Rome, Italy

Maybe it’s the crowds, or the somewhat metropolitan feel, or the overall sprawl of this city; but for one reason or another, it seems many visitors don’t have the fondest feelings toward Rome. And that just breaks our hearts.

The first time we traveled to Rome, it was for a simple day trip from Florence. An easy 90 minute train ride brought us into Roma Termini (the city’s main train station), and from there our day became a whirlwind of walking, sightseeing, tourist-elbowing, and sweating. We checked off the Roman Forum, the Colosseum, the Spanish Steps, Trevi Fountain, the Pantheon, and even a trip through the Vatican… all within about 7 hours. Unsurprisingly, I was nearly in tears by the time we got on our evening train back to Florence. So yes, we totally understand how Rome can be overwhelming.

Thankfully, we learned some valuable lessons from our rookie mistake. We learned that it’s okay to travel somewhere without visiting EVERY “must-see” spot in the city. In fact, it’s how we prefer to travel these days. We mentioned this in our Florence post, but it applies even more so to a bigger city like Rome: take your time. The Eternal City has stood for thousands of years – it would be a shame to rush through some checklist while missing all of the quietly immense details that make this city truly awe-inspiring.


Getting Here

Rome’s Fiumicino airport (FCO) is a major international hub, meaning it’s accessible from most airports/cities. We typically fly to Rome on AerLingus via Dublin, but this time we decided to splurge a bit on a direct flight from Boston to Rome (it was our honeymoon after all!). We upgraded our tickets and enjoyed an extremely comfortable 9 hour flight. Alitalia consistently wins awards for the food offered in its business class cabin, and now we understand why. Truly, Alitalia’s business class experience almost made me wish I didn’t fall asleep for 90% of the flight.alitalia

On our return trip, we arrived at the airport a few hours early (since I am one of those crazy people who lives in constant fear of being late for a flight). And we are so glad we did! The Alitalia lounge in FCO is one of the best lounges we’ve been to – the bar has a full selection of beers, wines, champagnes, and alcohol, and the FOOD is better than what you’d find in many restaurants (prosciutto, fresh pasta, beautiful salads). It was the perfect end to our honeymoon (and made it even harder to leave!).


Staying Here (Economy)

Hotel Giolli

Via Nazionale 69, Rome, Italy

Hotel Giolli (“Jolly”) is easily our favorite hotel in Rome. It’s extremely conveniently located: less than a 10 minute taxi from Roma Termini, and also about a 10 minute walk for the light packers out there. The rooms are spacious and comfortable, and the nightly rate includes a standard Italian style breakfast [meats, cheeses, fruit, pastries, and endless espressos]. Many of the rooms also have high ceilings covered in beautiful frescos, which adds a luxurious feel during your very affordable stay. Without a doubt, this will be our go-to hotel for all future trips to Roma.

Staying Here (First Class)

Waldorf Astoria Rome Cavalieri

Via Alberto Cadlolo 101, Rome, Italy

Unfortunately, our first class stay at Rome Cavalieri was not an experience we would recommend to friends, family, or readers. Long story short, we paid a first class rate for a less-than-first class experience*. Check back in after our next trip to Rome (hopefully soon!) for a new and improved suggestion.


*The plus side, however, was this view.

Spending the Day


If you look up any travel book or online guide for visiting Rome, they’ll likely all have a similar “must see” list – Colosseum, Roman Forum, Pantheon, Trevi Fountain, Spanish Steps, Piazza Navona, Campo de’Fiori, St. Peter’s & the Vatican, etc. And yes you should definitely try and see all of these incredible landmarks during your lifetime. But we have a few tips and tricks for making the most of your time in Rome without wanting to run away and hide in a quiet dark space:

  • Wait for nightfall to hit the major tourist spots – If you make an attempt at visiting Trevi mid-day, there’s a good chance you’ll actually just end up seeing the back of 1000+ tourists’ heads. Our favorite way to take in the stunning architecture and fountains of Rome is during a late-night, after-dinner stroll. The temperature drops significantly compared to mid-day, and you’ll be able to admire the world-renowned sites in your own space and at your own leisure. They’re also all lit up so beautifully that you’ll wonder why anyone chooses to do this in the day time!


  • Cool off in the Borghese Gardens – As mentioned previously, mid-day in Rome is hot. Our favorite way to stay cool is in the shadows of the gardens of Villa Borghese. These sprawling gardens include ponds, fountains, walking paths, and plenty of spots to cool off or take in a view of the city. Insider tip – rent a motorized bicycle! It’s only about €10 or €15 for an hour of childlike joy. Plus, the Italians don’t care so much about things like “rules” or “safety,” so you can take it wherever you want and enjoy a Peroni or two on the ride.
  • Shop – If you’ve ever noticed how painfully chic Italian men and women are, the best thing you can do for yourself is start shopping at their stores. Even the H&Ms in Italy have much better pieces than you’ll find in the states. Even better? Most of the shops are air conditioned.


Insider Tip – For only a few euro, you can take an elevator up to the roof of St. Peter’s Basilica! 


Pre-Dinner Drinks (Economy)


Via del Moro 8, Rome, Italy

For those of you who don’t know, one of Mike’s hidden talents is foosball. Born from many childhood hours in friends’ basements (or many slow hours at a tech start-up), Mike’s foosball talents are pretty much unmatched. Challengers welcome. So any time we pass a bar with a foosball table, we’re obligated to stop in. Thankfully, 8millimetri’s drinks were delicious enough to distract me from yet another embarrassing loss.

8millimetri’s cool interior fits in perfectly with the relaxed vibe of the Trastevere neighborhood. The theme is a subtle nod to old Hollywood movies (hence the name), and the space is filled with comfortable chairs and couches to chat with friends. 8millimetri also offers a varied (and delicious looking) spread for aperitivo; however, we passed on the nibbles since we were saving our appetite for our favorite restaurant in Rome. Read on below!


Dinner Date (Economy)

Margo G

Via Garibaldi 56, Rome, Italy

As Mike’s favorite date flight restaurant in the world, you know there has to be something special about Marco G’s. We were lucky enough to have our “farewell dinner” at Marco G’s during our wedding week. Marco himself was incredibly helpful and accommodating in putting together a special evening for friends and family who traveled so far to attend our wedding, but you’ll experience the same hospitality even just wandering into the restaurant from the street.


Now, about the food. First things first, do yourselves a favor and order the meat and cheese platter to start the meal. It’s an extremely generous serving and the smoked mozzarella will speak to your soul. Take your time on the appetizer since your next dish is a bit heavier – truffle and sausage pasta. I don’t even like truffle and this is one of the most incredible pasta dishes I’ve ever eaten. Everything on the menu is truly delicious, but we know from personal experience that you’ll be talking about these two dishes for months after you leave Rome.

If you need any further convincing, just know that two date flights friends were in Rome for 3 days for their honeymoon.. and ate dinner at Marco G’s twice. And we would do the exact same thing!


Dinner Date (First Class)

La Pergola

Via Alberto Cadlolo 101, Rome, Italy 

Our dinner at La Pergola may go down as one of the most incredible meals of our lives. Located on the top floor of the Rome Cavalieri, we dined at sunset on the spacious deck overlooking all of Rome. The setting was so beautiful we kept having to make sure it wasn’t actually a green screen. However, we were quickly distracted from the incredible view when the food and wine arrived.

In typical date flights fashion, we ordered the gourmet tasting menu with wine pairing*. Every bite was delicious, but we’ll remember the Fagottelli “La Pergola” forever. Picture the best carbonara sauce you’ve ever had, except it’s contained inside of the pasta, creating a saucy explosion as you bite through the perfectly prepared fagottelli. Mind-blowing is the only way to describe this dish.

While we wouldn’t stay at the Rome Cavalieri hotel again, we will definitely be back to La Pergola.

*Usually wine pairings = one glass of wine per dish. Not here! Our servers kept the wine flowing all night as we worked our way through 10+ courses.


Have you been to Rome? Did you love it as much as we do? 



Edinburgh, Scotland

Edinburgh* is a city that you just want to get to know. It welcomes you with open arms and invites you to explore each nook and cranny in your own time. Around every corner is another pub to warm up in by a fire or another cafe to read the afternoon away. Read on below for details about our romantic, adventurous, historical, exciting, and charming getaway to this timeless city.

*It’s pronounced “Edinbur-uh” – emphasis on the first syllable, with the last syllable just meant to sort of fall out of your mouth.

Getting Here

There are a handful of relatively easy ways to get to Edinburgh from the Eastern US – this time we took Aer Lingus to Edinburgh Airport via Dublin. We do a lot of traveling throughout Europe with Aer Lingus – Dublin is a great stepping stone to most of the continent, prices are very reasonable, and the service is far above their low cost competitors. We’ve taken the new A330 business class before (which is an awesome value), but as this trip was sort of last minute, we opted to go economy and get a 2 seat row closer to the front on the BOS->DUB leg. On the final leg into Scotland, we took a ATR-72. This was our first time on a turboprop plane… It felt a little bit like being on a school bus, that goes 400+ mph 20,000ft above the ground. Very interesting experience! If you like flying, and trying new experiences – we certainly recommend it.

Mike’s personal favorite way to get to Edinburgh is via the East Coast Train. Unfortunately this requires a bit more work: flying into London (usually Heathrow), then getting into Central London (via Heathrow Express), then either walking or taking the tube to Kings Cross/St. Pancras to catch the East Coast to Edinburgh Waverly Station. We know what you’re thinking, “that sounds fucking terrible” and honestly, it kind of is. But! The views of the English & Scottish countryside through the Midlands and coastline are nothing short of spectacular. So if you’ve got some extra time, or are feeling a bit adventurous – give it a go!

You can also fly directly to Edinburgh from dozens of European cities, as well as JFK (NYC) with American & Delta, O’Hare (Chicago) & Newark with United, not to mention Doha and Abu Dhabi on the Arabian Peninsula with Qatar Airways and Etihad. Seems like more and more routes get added every year. Fingers crossed for a direct to Boston soon!

edinburgh flight


Staying Here (Economy)

Motel One

18-21 Market Street, Edinburgh

In the states, any place named “Motel (Number)” is likely somewhere you’d want to bring your own sheets and try your best not to touch any surfaces. Motel One in Edinburgh does not fit that mold. Clean, modern decor, plenty of pillows (very important to the date flights team), and less than a 3 minute walk to The Royal Mile made Motel One the perfect economy stay for our first few nights in Edinburgh. And since the hotel is literally across the street from the city’s main train station, getting to and from the hotel with your luggage is no issue.

We arrived in Edinburgh early in the morning after a sleepless red eye, so we headed to Motel One hoping against hope that we’d be able to check in early. Thankfully our room was already available for us, so we gratefully dropped our bags off and quickly showered before heading out to explore the city (read on below!). Pro tip – when traveling to a materially different time zone, try your absolute best to stay awake your first day until a reasonable sleeping hour (hey, 7:30PM is totally reasonable…) Even though Edinburgh is 5 hours ahead of Boston, we were able to fully adjust within one day by not taking an oh-so-tempting nap on our first day. And while Edinburgh’s northern location makes late night dinners and walks through the city absolutely magical (sunsets at 9PM or later!), we were certainly happy to close Motel One’s blackout shades well before sunset on that first night…

Staying Here (First Class)

The Witchery

Castlehill, The Royal Mile, Edinburgh


Like many couples, the date flights team embodies the idea that “opposites attract.” He – loves spontaneity, shoots first asks questions later, is competitive to a T, dreams big and goes after what he wants. She – loves order and routine, makes lists (and the bed. everyday.), thinks change is hard, and analyzes each potential outcome before making a decision.

So when Mike requested we make the impromptu decision to delay our flights and stay one more night at the Witchery, no one was more surprised than me when I said, “Yes.” In all honesty, though, the decision was less driven by my increasing spontaneity (still working on that) than it was by how utterly magical the Library Suite at the Witchery is. As the concierge was giving us the grand tour of the apartment-style rooms, we couldn’t help exclaiming, “Are you KIDDING me?!” at every turn. Doors hidden behind panels of books, a full-sized dining area, red velvet everywhere, and well-worn books throughout the space proved that no detail had been overlooked in creating this romantic escape. Not to mention we were greeted by freshly baked cookies to be washed down by a bottle of chilled champagne just dying to be popped. Plus, two of the DVDs available to watch were from the Harry Potter and Lord of the Rings series [seriously, did the concierge do some internet creeping to know exactly what we would want in a hotel room?!].

witchery bathroom

Now, on to the details: The Witchery’s restaurant and rooms are located right on The Royal Mile in the heart of Old Town, mere steps away from Edinburgh Castle. Each room available for booking at the Witchery is actually an apartment style suite. The Witchery opportunistically buys up available apartments in the area and converts each into its own themed getaway, complete with kitchens, sitting area(s), and stunning bathrooms. Breakfast is included in the price of the room and will be delivered to your suite each morning, so there’s really no good reason to get out of your plush bathrobe before noon. The service was impeccable, and the night clerk even delivered a very early breakfast to us when we had to leave for the airport at the crack of dawn. The only way to appropriately describe our time here was decadent. We opted to order take away both nights of our stay since we didn’t want to spend any more time away from the rooms than absolutely necessary.

We couldn’t imagine a more enchanting end to our time in the birthplace of Harry Potter than to spend our final nights in Gryffindor Tower. I guess this almost makes up for the fact that I still haven’t received my Hogwarts letter…

Spending the Day

We did a PRETTY good job making the most of our time in Edinburgh, if we do say so ourselves. Whether you want to be active (#fitness), soak up the historical and/or literary significance of the city, or just spend 12 hours day drinking (no judgment!), Edinburgh will provide. Our first morning in the city we fueled up with a light full-Scottish breakfast then headed straight to Holyrood Park to hike up to the highest point in the city. Holyrood Park is an easy 15-20 minute walk from the city center, followed by a not so easy hour long hike up to King Arthur’s Seat. But trust us, the views are worth the effort! Plus, the pints you have after your hike will taste like victory and burned calories.

arthurs seat

Edinburgh Castle is certainly worth a visit, and its convenient location at the top of The Royal Mile made it an easy walk from our hotel. The castle and surrounding grounds are beautiful, especially at sunset (which lasted for almost an hour during our time in Scotland!). We even took a walk well below the castle wall to the spooky cemetery which lays at its feet. The view from the cemetery gave us a truly awe-inspiring appreciation for this impenetrable structure that has endured the test of time. And after all that learning you do, make a stop in the gift shop where you can taste and buy Edinburgh Castle’s own malt whisky.

And last but certainly not least, you know we couldn’t take a trip to Edinburgh without paying homage to the true queen of the UK, JK Rowling. We spent a full morning hitting up all of the relevant Harry Potter sites throughout the city – below are some of our favorites:

  • The Elephant House (21 George IV Bridge, Edinburgh) – We got Irish coffees here (or would they be Scottish? either way they had whiskey in them) and enjoyed the view of Edinburgh Castle and Greyfriars Kirkyard (inspiration for Tom Riddle Sr.’s cemetary!)
  • Spoon (6A Nicolson St, Edinburgh) – I think this was actually a Chinese restaurant back when JK Rowling was a regular, but now it’s a completely charming cafe that we could have easily spent endless hours reading, sipping iced coffees (Yes! They had delicious iced coffee here! A true rarity in the UK…), and soaking up the HP magic that’s left its imprint in each floorboard and colorful table.
  • Greyfriars Kirkyard (Candlemaker Row, Edinburgh) – See above. Super spooky.
  • George Heriot’s School (Lauriston Pl, Edinburgh) – Allegedly the inspiration for Hogwarts School of Witchcraft and Wizardry, Heriot’s almost looks like it was placed into a green screen of the Edinburgh skyline. With its stunning architecture and system of dividing students into four “houses,” it’s easy to imagine Hogwarts existing in a parallel universe to Heriot’s.
  • Victoria Street / The Royal Mile / Every close – We spent almost every minute wandering around Edinburgh imagining we were actually moseying through Diagon Alley. Actually, now that I think of it, we really should have started tapping on brick walls above every trash can in the city…

spoonSpoon, now one of our favorite cafes in the world. You can see why!


Pre-Dinner Drinks (Economy)

Wings Edinburgh

5-7 Old Fishmarket Close, Edinburgh

What’s that old saying? “You can tell everything you need to know about someone by which character they use in Mario Kart.”? Something like that. The fact that this bar has Mario Kart (on N64 no less) automatically makes it one of our favorites, but Wings Edinburgh offers so much more than that (like Goldeneye!). Everywhere you look, there is something sweet to geek out about, including a T-Rex head mounted to the wall above the Jurassic Park themed table (we sat at the also-awesomely decorated Star Wars table, but definitely felt a pang of seat-envy when we saw  a dinosaur staring down at us from the opposite wall).

Apparently the bar’s owner decided to open Wings after visiting the US and Canada, where he realized what a tragic mistake Scotland was making by not offering fried, saucy chicken for late night drunchies. Whether you choose to come here before dinner (more drinks, less wings) or for late night shenanigans, it’s impossible to not have fun on a date at Wings Edinburgh.

Pre-Dinner Drinks (First Class)

ensign ewart

Ensign Ewart

521-523 Lawnmarket, The Royal Mile, Edinburgh

For one reason or another, we’ve always idealized the culture and countryside of the UK. Likely born from lifelong obsessions with the likes of Tolkien, Lewis, and Rowling, we find ourselves drawn to images of thatched roof cottages, rolling green hills divided by perfectly imperfect stone borders, and – of course – every village and city’s quintessential pub. We’ve been lucky enough to visit a number of cozy, low-ceilinged pubs that serve up no-nonsense drinks and simple, soul-satisfying food. And of all the pubs in all villages and cities we’ve been to, Ensign Ewart is without question our favorite. During the four days we spent in Edinburgh, we went to this pub no less than five* times. Whether it was for a quick pre-dinner drink, a victory lunch after a climb to King Arthur’s seat, or a leisurely afternoon tasting Scotch flights, Ensign Ewart hit the spot. Every inch of this pub is charming and welcoming, but we were especially partial to the nook in the very back corner of the pub.Two small tables and benches face off beside a fire, providing the perfect spot for conversation. The set-up made us feel like we were in a private room, while also having a great view of the single-man kitchen and a chalkboard with helpful tasting notes for all of the Scotches we’d be tasting, organized by region.

inside ee

*When it became obvious (upon our fourth visit) how much time we were spending in Ensign Ewart, we thought it would only be fair to give some love to Edinburgh’s many other pubs. Our final day in Edinburgh was spent grabbing one drink each in more than ten pubs throughout Old Town (Thistly Cross ciders for her, golden ales for him, and some Scotch thrown in for good measure). And while they were all charming and cozy and perfectly good pubs in their own rights, Ensign Ewart is simply the best.

Dinner Date (Economy)

The Devil’s Advocate

9 Advocate’s Close, Edinburgh

Price: ££

Edinburgh’s Old Town is basically comprised of the high street (equivalent to main street, a.k.a. The Royal Mile), and small alleyways leading off high street to the north and south. The Scots call these alleyways “closes,” and after about 5 minutes spent walking around the city it quickly became a life goal for us to live in an apartment on a close in Edinburgh. The relatively high elevation of The Royal Mile means that many of these closes have pretty steep inclines and plenty of stairs, and Advocate’s Close is no exception. Advocate’s Close also conveniently led directly from Motel One to The Royal Mile, so when we were climbing up the close’s (many) steps and saw the restaurant’s cool exterior and amazing location we made a mental note to check it out (maybe when we weren’t so sweaty and out of breath).

Devils Advocate

Later that night when we entered the loft-style restaurant through the stonewalled bar on the first level, we knew we had made the right choice for our first dinner in Scotland. This is exactly the type of place we’d want to come for after work drinks when we inevitably move to Edinburgh 😉 In warmer months the restaurant offers outdoor seating and opens up its huge wooden doors to look out over the close and city below, but this time we ate up in the loft overlooking the bar area below. The menu was the perfect entry to Scottish fare, offering classics (like fish and chips) and some hip modern dishes (like pork belly with Asian slaw). The Devil’s Advocate also has a great whisky selection, but we opted for a few casual pints since we had, at this point, been awake for almost 30 hours.

The Devil’s Advocate set the perfect tone for our first date in this incredible city.. and was worth every stair it took to get there.

Dinner Date (First Class)

The Witchery

Castlehill, The Royal Mile, Edinburgh

Price: £££

At this point, you’ve already read all about our unforgettable stay in the rooms at The Witchery. So it should come as no surprise that the establishment’s restaurant is one of the most romantic places we’ve ever eaten. The Witchery has a very tempting a la carte menu, but of course we opted for the (reasonably priced!) 3 course tasting menu for £35. Everything we tasted was delicious – especially the short ribs – but the restaurant’s atmosphere is what truly stands out.

witchery entry

We dined in the Secret Garden room, so the name alone should give you a good idea of what to expect. And even though we arrived at the restaurant ready for an amazing experience based on everything we had read and heard, each of our expectations was blown away. The restaurant is tucked away down a stone alleyway, which suddenly opens onto a lush garden and iron-gated stone house. We truly felt as though we were walking into a fairy tale as we descended the staircase to the Secret Garden. Eating delicious food, sipping a fruity Brunello, and gazing out into the wildly beautiful garden covered in hours of twilight glow… The Witchery takes romance to the Nth degree, and does so with sophistication (and just a touch of magic).

Have you been to Edinburgh? Did you love it as much as we did? Comment below!

Boston, Massachusetts USA

There are many words one could use when describing Boston. Historic. Educated. Opinionated. Sports. Chowdah. And while all of these are true [on some level], to us, there are two important characteristics that help define this city. First, Boston is extremely walkable. Since chances are high that you won’t be visiting in the dead of winter, take advantage of the good weather and hit the streets. This is by far the best way to experience Boston and begin to understand the personality of its neighborhoods. Which brings us to our second point – Boston is a city of neighborhoods. You can jump to a lot of conclusions about someone based upon which neighborhood they choose to live in. So see our brief and abbreviated neighborhood guide below to get a feel for some of Boston’s many personalities:

  • Allston / Brighton: College kids. Great / cheap Asian food
  • Back Bay: Old money. Picturesque. High end shopping
  • Beacon Hill: Charm, charm, and more charm. Brick everywhere
  • Charlestown: Downeast Cider Company. Charming gaslight district
  • Chinatown: Self-explanatory
  • Dorchester: Up and coming
  • Downtown: Financial district. Commercial buildings. [Do people actually live here?]
  • East Boston/Eastie: Hispanic and Italian influences. Another up and comer
  • Fenway: Self-explanatory. Also some college kids
  • Fort Point: aka New Waterfront. Happening bar and restaurant scene
  • Jamaica Plain: Sam Adams brewery. Hippies, hipsters, and young families
  • North End: Heavy Italian influence. Paul Revere. Young professionals. [Our personal favorite]
  • South Boston/Southie: Bros and yo pros. The fraternity/sorority of Boston. St. Patrick’s Day
  • South End: Gentrification at its finest. Restaurants. French bull dogs

Reflecting Pool

Really though, don’t take our word for it. Get out there and start walking!


Getting Here


Boston’s Logan International Airport is one of the most well connected hubs in the country. With direct flights from 80+ cities domestically and around 75 international locations, getting here is pretty easy from just about anywhere in the world!

Logan is conveniently located 5 minutes outside of the city center [traffic willing]. Unfortunately, there are a ton of tolls between the airport and most downtown destinations. So expect to pay $20+ for a cab from the airport to your hotel, even if you’re barely in it long enough to get comfortable.

Alternatively, you can hop on the Silver Line [a bus-subway hybrid] right from Logan Airport and get to any destination within the MBTA’s network for less than $3 per person… but we prefer cabs.

Staying Here 

While there are a lot of hotels in Boston – and some very nice ones at that – most are quite expensive. And although the historical significance of city adds lots of charm, it also means many hotels are located in old buildings with small(er) rooms. Your best bet is to start with AirBnB, giving you the opportunity to stay in central locations for less than $400-500/night.

But if you do want to stay in a hotel downtown, we would recommend the Ames or Langham – both are beautiful, boutique-y, and conveniently located with great service to boot.

Luckily for us, we live here – so hotels are never an issue. 🙂

North End
Our own neighborhood – the North End a.k.a. Boston’s “Little Italy”


Spending the Day

As we mentioned, the best way to spend your time in Boston is walking to and from all of the great sites (and bars and restaurants!). We would definitely recommend walking the Freedom Trail, which will take you near the Common, all over the financial district, the North End, and even into Charlestown. Completing this walk on one of your first days will help get you acquainted with the city’s layout while you take mental notes on which areas you’d like to visit in more depth.

Swan Boats

If the weather isn’t cooperating or you’re just looking for some indoor time, head to one of Boston’s many great museums. The Museum of Science, MFA (free on Wednesday nights!), Isabella Stewart Gardner Museum, and the Aquarium are all fantastic options that are easily accessible on foot or by public transit.

For you shoppers and foodies out there, a visit to the Boston Public Market* (adjacent to the North End) and the SoWa Open Market (South End) should definitely be on your itineraries. Boston also has an excellent local brewery (and even distillery!) scene. DownEast Cider Company, Sam Adams, Harpoon Brewery, Night Shift Brewing, and Boston Harbor Distillery are some of our favorites.

North End Green

If you opt for renting a car during your stay, or are comfortable using public transportation (the T aka subway is color coded, cheap, and extremely easy to navigate), there are great day trip options all around the city. While Boston is the true capital city of Massachusetts, it also serves as the pseudo capital for all of New England. In 90 minutes of driving (or less), you could be on a beach on Cape Cod, walking among the mansions in Newport, learning about the pilgrims at Plymouth Rock, hiking the White Mountains in New Hampshire, or apple picking among the abundant fall foliage (anywhere in October/November, really).

Fall Foliage 2

After all of the walking, learning, and site seeing you’ll have done, you deserve some refreshing drinks and delicious food. Read on below for some of our favorite options! 

*Get a bag or four of apple cider donuts from Red Apple Farm in the Boston Public Market. They’re fried fresh and melt in your mouth. Plus, their miniature size makes you feel better about eating 10 in a row

Pre-Dinner Drinks (Economy)

21st Amendment

150 Bowdoin Street, Boston, MA

Boston, at its roots, is a historic city. It’s the rebellious older brother who  stood up to the Redcoats, threw tea into the harbor, and basically “invented America.” But it also has a more demure side, entrenched in the city’s Puritan foundation and evidenced throughout its drinking culture to this day. Liquor stores close early on Sundays (if they open at all), selling discounted drinks is illegal, and until recently no alcohol could be delivered to a Massachusetts address.

Thankfully, though, we live in Boston in a post-Prohibition era, so we get to enjoy bars like 21st Amendment as often as we want. We first stopped by this Beacon Hill tavern on a snowy February afternoon when we were craving some classic bar food and English country-style pub atmosphere. And that’s exactly what we got. 21st Amendment’s low ceilings crossed by dark wood beams, cushy seats next to cozy fireplaces, and short rib grilled cheese sandwiches make it the perfect place to spend a weekend afternoon. Better yet, stop in for just a drink before heading down the street for dinner at Grotto [read on below!]

Pre-Dinner Drinks (First Class)

Carrie Nation

11 Beacon Street, Boston, MA

Given Boston’s sometimes prudish drinking culture, it’s no surprise that one of our favorite spots to grab a drink is at the resident speakeasy – Carrie Nation. Named after a radical member of the temperance movement, Carrie Nation ironically serves up delicious craft cocktails under the disapproving gaze of its namesake painted on the walls. The spacious front bar is a great spot to grab drinks and $1 oysters (Monday & Tuesday only), but the establishment’s real draw is tucked away, down a long hallway, behind a velvet curtain. If you venture into Carrie Nation’s back room, you’ll understand why it’s known as a speakeasy. Low couches, pool tables, and discrete lighting bring you back to a time when you had to speak a password before the good stuff could pass your lips. Thankfully, no passwords are required here, only patience – the back bar opens at 5PM each night. Get there early to snag a cozy armchair or corner table and watch as the debauchery unfolds.

Insider Tip
Bourbon lovers beware – Carrie Nation serves up our favorite old fashioned in the city.

Honorable Mentions:
The Seaport neighborhood also has some great first class bars to hop around, especially in the summer. Try Del Frisco’s for a delicious martini and panoramic views of the harbor, or head on up to the third floor of Legal Harborside for al fresco drinks on the roof deck.

Dinner Date (Economy)



37 Bowdoin Street, Boston, MA

Dress: Casual, but since we usually go here for date night, we like to get dressed up and don’t feel out of place at all

Price: $$

There’s no point in sugar coating this – March in Boston is gross. It’s either (A) still snowing, windy, and freezing all the time, (B) just warm enough to half melt the snow that accumulated all winter and turn it a lovely shade of gray-black, or (C) some combination of A and B. Thankfully for residents of Boston, Restaurant Week usually falls within the first few weeks of March, giving us that final push of energy to get out of the house and into spring-mode.

Boston’s Restaurant Week usually spans 10 business days [two weeks Monday – Friday], with nearly every restaurant in all neighborhoods offering discounted prix fixe menus. It’s great for diners and businesses alike, since most Bostonians that we know make it a point to try at least one new restaurant for lunch or dinner whenever Restaurant Week rolls around.

At this point you may be wondering why this post is titled “Grotto” instead of “Restaurant Week”… well, the best thing about Grotto is that it offers Restaurant Week deals all year round. For $35 or $40 per person, you get a delicious 3 course Italian meal in one of the most romantic restaurants in Boston [the price depends on if you choose a pasta or meat dish as your main course]. The restaurant itself is located in the garden level of a brownstone building in Boston’s stunningly charming, old money-oozing Beacon Hill neighborhood. Brick walls, low red ceilings, and flickering candlelight make Grotto the quintessential date flight choice in Boston.

Our personal menu favorites include the grilled calamari, fra diavolo, gnocchi, anatra, and the banana bread pudding. Really though, no matter what dishes you choose, you’re in for a deliciously romantic night at Grotto.

Insider Tips
1) The gnocchi with short ribs, mushrooms, and gorgonzola are nothing short of life-changing. And this coming from someone who does not even like bleu cheese!
2) There’s a corner table – in the front, all the way to your left when you walk in the door – that may be our favorite singular place to eat in Boston. Getting a seat at this table makes you feel like you’re in a private nook designed just for you and your special someone, and gives you a great vantage point for people watching if conversation lulls. When making your reservation, it’s worth asking the host/hostess for that corner spot whenever the table is available.

Dinner Date (First Class)


354 Congress Street, Boston, MA

Price: $$$$

Two years ago this summer, the date flights team gave up on giving each other gifts. Sixteen birthday celebrations, eight anniversaries and Christmases, three years of living together, and one wedding all combined into a whole lot of stuff and very few original gift ideas. And if you happen to know one thing about real estate in the North End, it’s that space is limited. So the decision to nix the gift exchanges was an easy one. Instead, we’ve begun the celebratory tradition of surprise tasting menus. For every celebration, we trade off secretly selecting a tasting menu to try, booking the reservations, and ordering a Lyft. So the beneficiary truly has no clue where we are going until we arrive.

We’ll never forget the excitement of heading to our first surprise tasting dinner [well, it was a surprise for one of us!]. Our car was stopped along a side street in Fort Point, an industrial looking neighborhood on the cusp of becoming the next ‘hot’ food and bar scene in Boston. We had arrived at the crème de la crème of Boston’s culinary feats – none other than Barbara Lynch’s Menton.

If you arrive early enough, you can grab a drink at another Lynch establishment right next door – aptly named Drink! We had taken a little too much time choosing the perfect date night outfits, though, so we immediately sat down and got to business. The restaurant’s neutral décor is dominated by grays and whites and soft lighting, all of which combines to let the food on your plate truly stand out. Though, truthfully, the plates don’t need any help standing out. Half of our time was spent ogling the spectacles being placed in front of us – foie gras lollipops sticking out of a miniature grass field like two delicious flag poles; bread sticks shaped like twigs [“are you sure we can eat these??”] on a moss-covered tray; the entire meal was a sight to behold. And Menton’s menu is as delicious as it is creative, changing seasonally to capture the best flavors and ingredients of the year. We would travel far and wide to eat at Menton again, but a ten minute ride works too!

For us, there’s no better way to celebrate any of life’s milestones than eating a delicious meal with the person you love. Through all these years and all this stuff, we’ve come to realize how much more we value experiences [and flavors] than possessions. And for that, we have travel to thank.

Have you been to Boston? Are you coming to visit? Let us know in the comments, we’d be happy to provide more personalized suggestions! 

San Juan, Puerto Rico


One of the best parts of living in New England is being able to experience the distinct change of seasons throughout the year. We have hot summer days in beautiful coastal towns, stunning fall foliage on cool crisp days, and more often than not we cap off our years with picturesque white Christmases in December. But then January comes. Followed by February [thank god for Presidents’ Day]. And still March after that. These dregs of winter seem to be a never-ending cycle of dark mornings, cloudy days, and too many nights spent hiding under blankets on the couch. And even when it seems like the rest of the world is shaking off its winter layers and remembering how good it feels to see the sun before AND after work, Boston holds onto its grudges with sub-40F temperatures and relentless icy rain.

So yeah, it took basically zero convincing for the date flights team to book a somewhat impromptu trip to Puerto Rico for the last weekend in March. Hot beaches, blue water, and literal figurative buckets of piña coladas were calling to us from the Caribbean. We left Boston in a frenzy of excitement one Friday afternoon, with no more expectations than a few relaxing days on the beach defrosting from another New England winter. But what we found in San Juan blew every one of our expectations away. This wasn’t even our first time to PR. We were lucky enough to attend our first destination wedding in San Juan, but because of this it seems our memories of the island were mostly dominated by fun times with family and a blur of beaches, pools, and wedding activities.

We had no idea how HARD we would fall for Puerto Rico this time around… as in completely, head over heels in love with this Caribbean island. It’s gotten to the point that we’re pretty much constantly refreshing Puerto Rican real estate websites. But that’s another post for another day, hopefully…

Getting Here


Typically, when we take a date flight – it’s abroad. While Puerto Rico is an island in the Caribbean, it’s technically part of the US. That means a lot of great things for American citizens heading there; direct flights from 20+ mainland cities, no passport needed, same currency, etc. It’s basically like a 51st state – except most people speak Spanish (a lot are bilingual), it’s a kick ass island where the weather is always amazing, and its citizens don’t pay federal taxes… so maybe a bit different than being a 51st state? Anyways! Being a domestic flight, we had way more time than we anticipated after getting through security before we boarded, which left a nice long time to enjoy Bloody Marys/mimosas before boarding our flight.

At least out of Boston, JetBlue dominates the Caribbean – they fly direct to 5-10 islands depending on time of year, and offer a handful of direct round trips BOS->SJU daily. We had a bit of an outdated A320, and the FlyFi wasn’t working for the majority of the flight – but at JUST under 3 hours from take off to landing, we couldn’t complain too much! Especially once we were greeted by palm trees, gorgeous weather, and delicious food within MINUTES of touching down.

Taxis are super easy to get from the airport, they all speak English, and it’s a $20 flat fee (though tips are appreciated).

Staying Here (Economy)

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At Wind Chimes Inn | Acacia Boutique Hotel

1750 Calle McLeary, San Juan, PR | 8 Calle Taft, San Juan, PR

It’s pretty fitting that the first time we visited Puerto Rico was for my sister’s wedding, and our troupe stayed at two sister hotels in Ocean Park [hehe get it?] – the At Wind Chimes Inn and the Acacia Boutique Hotel. During that first trip, the date flights duo stayed in the At Wind Chimes Inn. Most recently, though, we opted for the Acacia experience. Both hotels are located within a 2 minute walk to the beach [Acacia is maybe 300 feet closer], and your room key will get you access to both properties regardless of where you choose to stay. While Wind Chimes and Acacia both give you the incredible feeling of staying in a gorgeous Puerto Rican home rather than in a typical hotel, the amenities listed below might help you choose the right sister for you:

  • Wind Chimes: secluded pool with beautifully flowering trees offering some shade in the hot PR afternoons, sun deck with lounge chairs, and a fully stocked bar
  • Acacia: THE most unique hot tub we’ve ever seen, Niche Bistro, and a slightly shorter walk to the beach

Pool Wind Chimes

Our room at Acacia also had a private balcony with a view of the ocean, which we took full advantage of for breakfast every morning and for pre-dinner Medallas every afternoon. There truly is no better way to start or end your day.

As you can probably tell by now, we can’t possibly say enough good things about these two hotels. And although we don’t know when we’ll be back to San Juan [soon, we hope!], we do know where we’ll be staying when we arrive.

Spending the Day

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There truly is something for everyone in San Juan. Whether you’re looking to brush up on your Spanish Empire knowledge, or trek your way through lush jungles,  or are just craving some sunshine and world class beaches, Puerto Rico has what you’re looking for.

History nerds? Head to Old San Juan and wander through El Morro. Formally known as Castillo San Felipe del Morro, this 400+ year old military fort has been beautifully preserved. Our time in El Morro was spent venturing down dark stone staircases, peeking into stark prison cells, and catching glimpses of the Caribbean Sea through old canon windows. This museum / fort does an incredible job of transporting its guests back in time, to an era when Puerto Rico was a most sought-after location for global powers to control.  


For the outdoorsy types, a trip to El Yunque should definitely be on the itinerary. This tropical rain forest is located ~45 minutes east of San Juan, so it’s best to rent a car if you plan to hike during your trip. And be sure to wear a bathing suit under your hiking clothes! Among the forest’s winding paths and colorful flora are natural springs where you can jump in and cool off. At the end of your hike, be sure to pop into one of the food huts near the parking lot. After all, you’ve earned that fried deliciousness.

Insider Tips
If possible, try and get to El Morro earlier in the day. The temperatures are much more suited for walking around, this usually-crowded tourist attraction will be yours to explore.
2) There is a luminescent bay about 45 minutes outside of San Juan. If you’re there at the right time in the moon’s cycle, you’ll be treated to a surreal nighttime experience in a secluded, glowing lagoon. No rental car? No worries! Kayaking Puerto Rico offers hotel pick up and drop off services within San Juan for only $20 per person.

Pre-Dinner Drinks (Economy)


La Cubanita

100 Calle San Francisco, San Juan, PR

Any bar worth its weight in San Juan will offer 2 for $4 Medallas during happy hour, and La Cubanita was no exception. And while the cheap happy hour offerings are what drew us in, it was the unbelievably talented and thoughtful bartender that kept us here until we had to rush to make our dinner reservation. With just a few guiding words from us, he managed to whip up the most delicious [non-piña colada] drinks we had on the island – including an old fashioned made with rum. No that’s not a typo, and it was way more delicious than it sounds.

During the two hours we spent here before our dinner at Marmalade [keep reading below!], I think we each said “this is probably the coolest place I’ve ever been” at least 5 times. Big open doors and windows peak out onto a colorful side street in Old San Juan, globe string lights hover over the bar, and shelves lining the wall inexplicably display household cleaning products and other sundries. There must be a backstory to the bodega vibe here… I guess we’ll just have to go back to investigate further!

Our time here even prompted us to start thinking of our favorite bars around the world, with La Cubanita right at home toward the top of our lists.

Pre-Dinner Drinks (First Class)

Barrachina Restaurant

104 Calle Fortaleza, San Juan, PR

Nine times out of ten, any restaurant or bar serving more tourists than local patrons is likely to deliver overpriced food in a cheesy atmosphere. Barrachina is that tenth time. Although the majority of dinner guests will likely be sunburned and just stopping over as part of a cruise [or loudly celebrating a bachelorette party], the piña coladas will make up for it tenfold. Our advise? Don’t let the tourists deter you.

When we first read that Barrachina was the birthplace of the piña colada, we knew we had to see and taste for ourselves. In the days leading up to our Puerto Rican date flight, we became solely focused on and excited about becoming piña colada connoisseurs. And after four days in PR [and many more piña coladas], we officially consider ourselves experts. Now, in our vast tropical drink experience, we can whole heartedly say that Barrachina’s blended concoctions are without parallel. The key? No ice. Yes, that’s right, you’ve been making piña coladas wrong your whole life [or at least we have!]. Instead, all of the ingredients are frozen and blended together, leaving you with the perfectly juicy piña to end all piñas. And be sure to ask for one to go on your way out – after all, Old San Juan is best viewed on foot, with a piña colada in hand.


Insider Tips
If you have a late dinner reservation, definitely get the Puerto Rican Delights appetizer to tide you over. Or skip dinner altogether and get the Special Sampler para dos. After all, calories don’t count on vacation.
2) For an authentically Puerto Rican experience, head to the La Placita one evening. This outdoor market area just south of Condado is chock full of bars and restaurants offering unbeatable drink specials and delicious food. It’s the perfect spot for an unplanned evening – pre-dinner drinks easily turn into a casual outdoor dinner followed by late night bar hopping. With no distinct lines or divisions separating the neighborhood’s bars, La Placita feels like a block party that everyone is invited to, locals and visitors alike.

Dinner Date (Economy)

Cafe Tresbe

Café Tresbé

1765 Calle Loíza, San Juan, PR

Dress: Casual

Price: $

In preparation for our latest trip to Puerto Rico, the date flights team decided it would be appropriate to work on our beach bodies a bit. Three and a half weeks, countless gym sessions, and too many ounces of chicken breast later, we couldn’t wait to veg out and enjoy the Caribbean lifestyle in full effect. During that month of hell prep, we managed to keep our sanity with weekly T(h)aco Thursdays at a local Mexican joint in Boston. So it was only appropriate that we sought out San Juan’s best tacos upon our arrival to the island.

Cafe Tresbe TacosEnter Café Tresbé. Located just a 5 minute walk from our hotel, this food-truck-turned-outdoor patio / juice bar / real bar / awesome hangout became one of our daily [and nightly] haunts. We ate our first meal in San Juan here, and to say we were deliriously happy at Café Tresbé would be an understatement. As you can see in the picture above, the atmosphere couldn’t be more fun or laid back. But the real star of Café Tresbé is the fish tacos. Without question these were some of the best fish tacos we’ve ever had – perfectly crispy, fresh fish topped with a to-die-for mango slaw and homemade hot sauce. Regardless of whether or not it happens to be T(h)aco Thursday, Café Tresbé is worth a trip any day of the week.

Dinner Date (First Class)

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Marmalade Restaurant & Wine Bar

317 Calle Fortaleza, San Juan, PR

Dress: Island Chic – not sure what the technical term is, but wear something fun & flirty! As with most restaurants on the island, Marmalade is air conditioned, so ladies – it wouldn’t hurt to bring a sweater or pashmina along with you

Price: $$$$

I’m not sure what we were expecting when entering Marmalade for our First Class Puerto Rican date flight, but it certainly wasn’t the modernist [and almost Middle Eastern?] island décor that awaited us inside. As soon as we sat down in our ridiculously comfortable chairs and had a chance to look around, we knew we were in for a treat. Marmalade perfectly balances modern style with comforting classics, both in the restaurant’s décor and on the chef’s plates.

Unsurprisingly, we opted for the six course tasting menu with wine pairing. And for the first time in our tasting menu experiences, we (1) had no clue what any of the dishes would be and (2) each got something different for every course! You have the option of hand crafting your own tasting menu, but we opted for the Chef’s choice since he is, after all, the expert. While we usually love getting to compare and contrast what we like in each dish, having two different menus allowed us to taste so many more dishes and wines than we would have otherwise. Plus, we got to be that cheesy couple feeding each other from across the table.

The food at this First Class establishment is delicious and completely unique, plus the restaurant offers four and five course tasting menus at slightly more affordable price points. Amazingly fresh seafood, bold spices, and stunning presentations [seriously, the plates themselves could be pieces of art] were the standard at Marmalade.

Insider Tip
Banana bread pudding with homemade rum raisin ice cream. Eat it.

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Thanks for reading! If you have been to San Juan and think there are other places we should feature on our next visit – let us know in the comments section.

Reykjavik, Iceland

Iceland, so hot right now. Iceland. Okay, so Iceland was anything but hot when we visited in March. But it is quickly becoming one of the most popular destinations to visit. Stunning landscapes, friendly locals, and easy flights from North America and Europe make a trip to Iceland basically a no brainer.

Our advice? Get there soon. Some of the most incredible and unique experiences we’ve had were seeing the awe inspiring sites of Iceland, and being almost entirely alone when we saw them. Our early morning flight into Reykjavik brought us to the Sun Voyager by 7am, where our first taste of Iceland included funky modern art, icy blue water, jaw-dropping mountains, and a sunrise that lasted an hour. And besides a few dedicated photographers who had risen early to catch the best light of the day, we were able to soak it all in by ourselves. It was the absolute perfect start to our trip, and ultimate consolation prize for not being able to check into our hotel until noon.

You may also have heard that you should only go to Iceland in the summer, since winters there are frigid and unpredictable. And while there is definitely some truth to the unpredictability of Mother Nature [if you don’t like the weather in Iceland, wait five minutes], the weather was basically very similar to Boston – dress smartly and you’ll be fine. Plus, the landscapes were coolly beautiful in March – white mountains, black sand beaches, gray skies, and unearthly green lava fields made us feel like we were alone on another planet. Not to mention – a TON of HBO’s Game of Thrones was filmed on location here. Even better? You have a chance of seeing the Northern Lights in the winter. [We, unfortunately, did not see them – but you can be sure we’ll be back again!]

Land Rover

Insider Tips
Forget the bus tours. Rent a car at the airport or in Reykjavik and spend your days road tripping around the island. Most of the hotels and apartment-style accommodations have parking access, and there’s nothing better than getting to pull over on the side of the road anytime you see something photo-worthy (which will be often!). Make a long playlist, stop at every gas station you see – for fuel, hot dogs, chocolate, and other necessities – and spend some quality time with your ride or die partner.

Getting Here – From Boston

Greenland winglet

Icelandair flies direct to Reykjavik from most major East Coast cities, and are even starting to expand to the Midwest (Chicago & Minneapolis) and even expanding further west to Denver, Seattle – even Anchorage Alaska!

We lucked out though, as Boston is the closest US airport offering flights to Iceland [for under $400 round-trip with 2 checked bags each]. Naturally, we were all over it and booked immediately.
The flight was a breeze, and the in-flight entertain was superb, offering a solid selection of newer movies and TV shows.
The only drawback would have to be the timing, particularly the time of arrival in Keflavik. Most (semi) transatlantic flights leave in the evening and get you to your destination the next morning. Unfortunately, since Iceland isn’t quite the same distance as, say, Rome or Munich – we touched down in Iceland at about 5:40am. Awesome. Fortunately, to kill time, we picked up our rental car and started the 40 minute drive to downtown Reykjavik to patiently await our noon check-in.
We experienced smooth sailing on the flight home too – we even got to fly in one of the cool Aurora themed planes (google it), and see the ice mountains of Greenland.
Insider Tip
Eat and buy nips before your flight – all food & drinks are a la carte, overpriced, and subpar. Aside from that we HIGHLY recommend Icelandair.

Staying Here (Economy)

Stay Brilliant Apartments

Brautarholt 2, Brautarholt, Reykjavík, Iceland

Affordable, apartment-style accommodations were exactly what we were looking for on our date flight to Iceland, and Stay Brilliant Apartments delivered. These no fuss apartments are conveniently located in downtown Reykjavik, with plenty of parking right outside. More importantly, they are next door to a top notch café [we started every day with a delicious cappuccino or three] and a short walk away from a Bonus grocery store [keep your eyes peeled for a drunk-looking pig logo]. In addition to having a fully stocked kitchen, where we prepped meals to supplement our frequent and necessary hot dog and chocolate gas station stops during our road trips, our apartment was stylishly decorated in modern and funky Nordic style. The apartment also had two bedrooms, more than enough closet space, a dining room table for 6, a full living room, and a small balcony which you can use to catch the Northern Lights in winter or to lounge on while sipping a sunset cocktail in the warmer months.

Stay Brilliant Apartments provide the perfect base for our stay in Reykjavik and for our road-tripping adventures across the island.

Spending the Day

Reykjavik skyline

Full disclosure: during our 5 days in Iceland, we didn’t get to spend as much time in the city of Reykjavik as we would have liked. We spent most of our days driving all over the western and southern parts of the island, trying to soak up as much of the Icelandic experience as possible – but the time we did spend in downtown Reykjavik was certainly memorable.

As soon as you start walking around, it becomes obvious that the roots of the city are residential. Unlike so many cities today – where the center is dominated by commercial buildings – much of downtown Reykjavik is stand alone single family homes. It has a very unique feel, definitely Nordic but still somewhat Western. This could be a result of the country’s recent increase in tourism, but it’s a city where most Americans, Brits, Canadians, etc. would feel right at home while still maintaining a charm and flavor distinctly Icelandic and all its own.


Must see stops in the city include the Sun Voyager, Hallgrimskirkja, Harpa Concert Hall, and the Pearl – and for the love of god, DO NOT leave Reykjavik without getting a hotdog from Bæjarins Beztu Pylsur. Voted best in Europe, this small stand is open until 1am most nights and 4:30am on weekends.

We would STRONGLY recommend renting a car (very unusual for us in a new city) and taking it all over Route 1 (only major “highway” in Iceland that runs the entire parameter of the country) to see the landscapes and other day-trip adventures. Our advice? Skip the tourist-packed Golden Circle and go see Snæfellsnes Peninsula one day and Vik, Jokulsarlon and the rest of South Iceland another.

Mountain + tractor

Snæfellsnes Peninsula – Known colloquially as “Mini-Iceland” – the wide array of unique landscapes that make Iceland so unique are also contained within Snæfellsnes. We drove north on Rt 1, then looped around the peninsula on Rt 54 (and around the tip via Rt 574), making a few unforgettable stops along the way. Most notably Djúpalóssandur beach and Bjarnarhöfn (the shark guy).

  • Djúpalóssandur: Ever wondered what it’s like to be Frodo, walking into Mordor? Just go to Djúpalóssandur. The black volcanic sand beach is nestled between two valleys of volcanic rock pillars that, when coupled with the remarkably blue waves, make this one of the most unique places we have ever been.
  • Bjarnarhöfn: If you’ve done any research on Iceland and traditional Icelandic food, you’ve probably read about the fermented shark. Bjarnarhöfn is THE place to get it. The family that runs the facility (which is really just one building and a shed) has been fishing Greenland Sharks like this for over 100 years. They catch them, butcher them, let them sit in crates for 6 weeks, then hang them up in the shed for 4-6 months. If you’re an adventurous eater – it’s a MUST.

Mordor - Iceland

South Iceland – We started this date by waking up before dawn to get to Myrdalsjökull glacier to do some snowmobiling with Extreme Iceland. Very cool experience, being North of the Wall on a snowmobile. Definitely worth it, plus it’s a chance to get up close and personal with your loved one as you can opt to share a snowmobile! After this adventure we took a few hour pitstop in Vik for lunch and some quintessential Icelandic wool swag. Vik is a super cute little town that deserves at least a few hours, if you have the time. Don’t forget to walk down to the beach and see Reynisdrangar before heading out. We decided to take this chance to get to Jökulsárlón, a glacial lagoon full of huge blocks of ice THOUSANDS of years old. Lucky for us there was also a ton of wild seals there soaking up some rays by the time we pulled in. There is just something so cool about seeing wild animals in a situation like that – felt like we were in an episode on NatGeo! And while we didn’t see any ourselves, word has it Jökulsárlón is a good place to catch an occasional glimpse of a wild Orca.

Jokulsarlon w: seals

To break up the 4-5 hour drive back to Reykjavik from the lagoon, we stopped at Sólheimasandur (just west of Vik) to see the wreckage of a crash landed US Navy Douglas DC3. After driving off road for a few miles, we came over the ridge of a hill to see a plane wreck. All alone on a black sand beach. Eerie. But one of the coolest sights on the island and not to be missed!

DC3 Wreck

Pre-Dinner Drinks (Economy)

The Dubliner

Hafnarstræti 1-3, 101, Naustin, Reykjavík, Iceland

Ah, The Dubliner – our home away from home in Reykjavik. Seriously, you could find us here at some point every night during our stay. This is the type of bar where anyone would want to be a regular. The Dubliner offers affordable pints, plenty of seating, candle-lit tables, and music quiet enough for you to actually hear your date talk. The kicker for us, though, had to be the foosball table. Nothing gets a fun date night started [or ended] better than a little healthy competition.

Loser buys next round 🙂

Pre-Dinner Drinks (First Class)

Dillon Whiskey Bar

Miðborg, Reykjavík, Iceland

First things first – get there early if you want to sit down. This whiskey bar gets pretty crowded, but never too loud or obnoxious for a few pre-dinner drinks. Also, they do live music Thurs-Sat, but thats’s not until later in the night.

If at least one of you enjoys whiskey this is a very cool stop before dinner. With over 100 whiskeys to choose from (Irish, Single Malt, Blended, American, Bourbon, Japanese, Taiwanese, and any other kind you can imagine) as well as expertly crafted cocktails and a selection of local Icelandic beers, it’s a pretty good bet you’ll enjoy your time here.

We got a bit adventurous and tried a Scottish Island single malt, a Speyside single malt and a Taiwanese whiskey (all on recommendations from Mike’s whiskey connoisseur friend) that we had never tried before, and still managed to make it to dinner in one piece!

Insider Tip
Dillons has some super rare single malts, so if you’ve ever wanted to try Macallan 25 or Balvenie 30 without spending $500-1000 on the bottle – this is the place.

Dinner Date (Economy)


Hamborgarabullan (a.k.a. The Burgerjoint)

Háaleiti S, Reykjavík, Iceland

Dress: Casual

Price: $ – we each got the Deal of the Century: classic cheeseburger, fries, and small soda for the equivalent of about 11 USD

Somehow or other, Iceland has figured out a way to perfect [what we used to think of as] classic American fast food fare. A tiny, standalone building near the water in downtown Reykjavik, The Burgerjoint is completely unassuming from the outside. Then you enter, and your brain starts to short circuit from everything happening around you. The open aired kitchen lets you watch as your patties turn to grilled perfection, all while the staff performs an intricate dance of cooking-while-staying-out-of-each-other’s-way [seriously, how do they fit 5 people back there?!] In summertime – or year round for braver souls than us – you can grab a picnic table outside, but in colder months it’s best to crowd together at tables or by the bar while you take in the restaurant’s twinkling Christmas lights, somewhat professional artwork, weirdly awesome knickknacks, and tantalizing smell of burgers and fries. Honestly, if you and your date run out of things to talk about during dinner here, it’s truly not be meant to be.

The Burgerjoint’s greasy-but-not-too-oozy, perfectly cooked, made-to-order burgers satisfied every one of our cravings after a full day spent exploring Iceland’s countryside. More than anything though, this joint has managed to flawlessly capture the Christmas spirit all year round – does it get more cozily romantic than that?

Dinner Date (First Class)

Puffin Sliders


Lækjargata 2A, 101 Reykjavík, Iceland (set back off the road, down a well-lit alley)

Dress: Dressy Casual

Price: $$$-$$$$

As you may know by now, here at date flights we love tasting menus. So when a friend recommended we give the tasting menu at Grillmarkadurinn a try, it was a no brainer.

Centrally located, Grillmarkadurinn is a short walk from most of the bars downtown [including The Dubliner]. When you first enter the restaurant, you can’t help but notice the attention to detail that went into building the space. Grillmarkadurinn pays homage to Iceland’s reverence of nature in every detail you see. Creative plates, smart applications of stone and wood accents throughout the décor, and easily the coolest bathroom we’ve ever seen [honestly, drink up] made for an unforgettable dining experience.

Our tasting menu was well-paced and allowed us to try dishes we could only taste in Iceland [including puffin and whale!]. Given the range of dishes and flavors presented, less adventurous eaters would be better off ordering their meals a la carte. No matter what dishes you choose, though, you should definitely – and this cannot be stressed enough – definitely order the potluck dessert. This dessert came as the final dish in our tasting menu and was nothing short of spectacular. Beautifully arranged… expertly prepared… it even came with some tableside presentation flair [think melted caramel + chocolate sphere + cake]. Every single bite was as delicious as it was beautiful. And really, what’s more sensual than sharing some caramel-y chocolate + ice cream + berry crumble + skyr sorbet bliss with your special someone?

Insider Tip
If possible, request a table downstairs when making your reservation. The meal will be delicious regardless of where you eat, but the atmosphere downstairs is truly unique and definitely worth asking for.

Snowmobiling date

Have a favorite place in Iceland we missed out on? Been to any of the locations mentioned above?

Let us know in the comments section!



Florence, Italy

If there’s a more romantic city in the world, the date flights team has yet to go there. Though, in full disclosure, we did get engaged and married in Florence, so we may be somewhat biased toward the home of the Renaissance.

The colors of this city are what come to mind first – all oranges and yellows and browns. It’s like fall in New England, only you get these magical colors all year round in Firenze.

Unfortunately, too many people make the mistake of seeing Florence as just another stop on a whirlwind tour of Italy. And while any amount of Florence is better than none, the best way [in our opinion] to experience this city is the same way Italians experience food – simply, never rushed, and always focused on quality over quantity. In many ways, it’s a lot like dating – you don’t want to rush into anything too fast here. If you try and cram in the Duomo, and the David, and all of the churches and museums that are Florentine must-sees in too short of a time span, you’ll just find yourself annoyed with the crowds, short tempered from the heat, and numb to the timeless, world-class beauty all around you.

Our advise? Take it slow. Spend your mornings tackling one of the giants of the city, and your afternoons strolling along the Arno, sunbathing in the Boboli Gardens, or sipping wine at the Piazzale Michelangelo. There’s a reason that life in Italy moves so beautifully slowly, and always has. Visit Italy the way the Italians live – trust them, they know what they’re doing.

Getting Here – From Boston

The closest major airport is Fiumicino Roma (Alitalia offers direct flights from a bunch of major US cities, and Aer Lingus offers a 1-stop option, via Dublin). From the airport, its super easy to take the Leonardo Express straight to Roma Termini (32 minutes and €17) where you can board a train straight to Florence (Firenze SMN) in about 1.5 hours via Trenitalia. The kiosks are all over Termini Stazione and are very easy to use. Trenitalia absolutely trumps Amtrak, or any other domestic US train service, in our opinion – not to mention the views on the train alone are worth staying awake for the duration! Hope you slept on the flight 🙂

Insider Tips
1) Unless someone is wearing a Trenitalia badge/uniform, don’t take their help – most of them are beggars and will simply help you book a train you could easily handle on your own, and demand a few €.
2) If you have time between getting to Termini and your departure to Firenze – go see the Colosseum! Its only about a 15 minute walk down Via Cavour, then a left on Via degli Annibaldi

Getting Here – From London


CityJet offers flights direct from London City Airport to Florence Peretola (formally Amerigo Vespucci). This was our first time flying CityJet, or out of the London City airport, and it was awesome. The airport was incredibly convenient from Central London (we were living in Bloomsbury at the time) and the flight was just under 2 hours!
There’s something so exhilarating for us, crossing over the Alps into the Italian airspace – the intricate patchwork of farms and fields of Lombardy & Emilia-Romagna, into the gentle rolling hills of the Tuscan landscape. No matter how long the travel before, no matter how jetlagged – that’s ALWAYS a source of excitement.
The small Avro RJ85 jet was surprisingly comfortable – leather seats, decent leg room, no complaints for a quick flight, and getting right from Central London into Florence was unbeatable.
Insider Tips
1) Florence can be a very windy airport, in which case landing a smaller plane can get interesting. Our advise? Take Dramamine before takeoff! One half of the date flights team gets horribly motion-sick, and Dramamine all but saved her life [and outfit] on a recent flight to Florence.
2) You can get direct flights into Florence from many major European hubs (Madrid, Frankfurt, Zurich, Amsterdam, Paris, to name a few) too.

Staying Here (Economy)

Albion river view

Hotel Albion

Via Il Prato, 22, Florence, Italy

If the date flights duo were to pick their favorite hotel room on earth, it would have to be the Frida Khalo room at the Hotel Albion in Florence. It’s not the biggest room in the world, or even at the Albion. It’s not particularly luxurious either, decorated in the sparsely rustic Tuscan style. There’s a lone window that looks out over the small rotary below and the Arno behind it. It’s simple, and it feels like home.

If you read the reviews of the Albion and its sister hotel [Le Boscarecce, a converted farmhouse out in the Tuscan countryside], the major theme that will come across is how the family behind this family-owned hotel sets it apart from all others. Sara, Susannah, Massimo, Nick, and everyone else you’ll meet at the Albion will truly make you feel like part of the family. Moreover, they’re always happy to recommend activities for your stay and book tours or reservations upon request. Susannah also happens to be an incredible cook [she and her daughter Swan made our unforgettable wedding meal], so you certainly won’t be disappointed if you opt for a night in.*

Now onto the actual details of the hotel: breakfast is included in the price of your room [pastries, hardboiled eggs, cold cuts and cheese, and the best blood orange juice on earth], as is reliable wifi, and access to the hotel’s bikes [though we do strongly believe the best way to see Florence is on foot]. The Albion is perfectly situated – just a few hundred yards from the Arno, and far enough away from the Duomo that you won’t be constantly surrounded by tourists but you’re also within easy walking distance of the city’s renowned sites. The décor is eclectic but comfortable, and all of the rooms are named after strong, famous women in history. Truthfully, it’s really the intangibles of this hotel that make it our number one choice – the people, the indescribable homey feeling, the old fashioned hotel keys… In short, we think one of our wedding guests described his stay at the Albion perfectly – “It’s not the nicest hotel I’ve ever stayed at, but it’s my favorite all the same.”

Whether it’s your first time at the Albion or your tenth, you’ll feel right at home using this as your base to explore this beautiful city. Guests who stay at the Albion always return on future trips to Florence. And you will too.

*We’ve never actually dined at the Albion after breakfast. Our wedding reception was at Le Boscarecce, where dinner is served daily. We have, however, seen guests eating dinner at the Albion so feel free to inquire!

Spending the Day

Florence Panarama

There are a few you things you really do have to do during the day while in Florence [see the Duomo; see Piazza della Signoria; go to Piazzale Michelangelo for sunset; anything you could find in a Rick Steves or Lonely Planet guidebook].

But there are a few slightly off-the-beaten-path things we HIGHLY recommend in addition to the staples:

Chapel of Princes – Connected to San Lorenzo Basilica, it almost looks like a mini-Duomo. This small chapel and sacristy is home to not only one of the most amazing spaces we’ve ever seen (the main chapel) but also several original Michelangelo statues and sketches on the wall. Prepare for a recurring theme during your time in Florence to be extremely prominent here: Medici.

Vasari Corridor – In 1549 when the Medici’s moved from Palazzo Vecchio to Palazzo Pitti, they realized they still had to get to Palazzo Vecchio every day for work. But, of course, they didn’t want to walk on the streets with the peasants [why would they??]. Naturally, Cosimo de’Medici had Giorgio Vasari build a secret hallway from their new home to their office in Piazza della Signoria. The Vasari Corridor winds through several buildings, behind a few churches [they didn’t even have to leave the hallway to attend mass], and right over top of the picturesque Ponte Vecchio. Tours of the corridor are offered irregularly, but it’s one of the most unique experiences in Florence.


Caffe’ la Terrazza – In the back of the 5th floor of La Rinascente in Piazza della Repubblica there is a flight of stairs that goes up to a small rooftop bar/cafe. This is the perfect place to stop for an espresso while exploring the city. As it’s relatively hidden, its never too crowded – and the views are amazing.

Rooftop Cafe - evening

Pre-Dinner Drinks (Economy)

Meat Market

Via Sant’ Agostino 23R, Florence, Italy

If anyone could figure out a way to improve the nearly perfect concept of happy hour, of course it was the Italians. Fun cocktails, good music, and as much food as you’d like to nibble on combine to create the perfect start to your Florentine night out.

Unfortunately we’ve heard tell that there are a few establishments in Florence that try to stretch their margins on aperitivo by offering second rate drinks and less-than-appetizing snacks. Take our word for it that MEAT Market is not one of those perpetrators. The bartender takes time and effort to create beautiful drinks [he even dressed up our mojitos like little matadors!], and there will be no shortage of delicious bites to curb your appetite until dinner time. Because, let’s face it, anyone going out to eat before 9PM in Italy is a huge dork. Beyond the seriously high quality food & beverage options, the shabby chic décor  and effortlessly cool vibe of MEAT Market will immediately make you feel like a trendy insider. This bar / restaurant is perfectly at home in the hip Oltrarno neighborhood.

To us, the perfectly casual evening in Florence starts with a stroll over to Oltarno at sunset, followed by a stop at MEAT Market for aperitivo, and ends with a leisurely dinner at Dante’s [taking care to save room for the world’s best gelato at La Carraia].

Pre-Dinner Drinks (First Class)

Westin Excelsior Rooftop Bar

Piazza Ognissanti 3, Florence, Italy

There’s just something that feels right about having a few cocktails on a rooftop, regardless of where you are in the world. Florence, with its picture-perfect skyline and beautiful climate, is no exception. We can’t think of a more romantic start to your First Class night out than sunset drinks at the Westin’s rooftop bar. Located right on the Arno, the Westin’s views of Florence, the river, and the too-good-to-be-true Tuscan landscape in the background will make you realize that life does not get better than this moment. Drinks are delicious, and the cost will be easier to swallow along with the free snacks that accompany your drinks [we had chips, nuts, and olives with our dirty ‘tinis].

Not ready for dinner yet? No worries! Pop across the Piazza Ognissanti – literally about 100 feet away – to the St. Regis Bar for round 2.

Dinner Date (Economy)

Trattoria Pizzeria Dante

Piazza Nazario Sauro, 12, Florence, Italy

Dress: Casual

Price: $$

Must: Get a bottle (or three) of the house wine

Trattoria? Pizzeria? Which is it?? Well, regardless of what you call it (we prefer Dante’s), this is one of our go-to date night spots in Florence. Each time we visit Florence, you can guarantee we’ll be eating dinner here at least once.

After spending all day walking and art-gazing in the birthplace of the Renaissance, the last thing any couple should want to do is elbow their way through a crowded and tourist-filled restaurant only to have a mediocre and likely overpriced dinner. Enter Dante’s: located in the hip Oltrarno neighborhood, the restaurant’s arched ceilings, soft lighting, and delicious house wine make it the perfect spot for a casual date night in Firenze. Everything on the menu is under €25 (and most dishes are around €15), and we’ve never had a bad meal there. Delicious, comforting food washed down with some of my favorite wine in the world is Italy at its best (seriously, the value of this house wine cannot be overstated – if anyone affiliated with Dante’s is reading this, please ship one five cases of wine to Boston as soon as possible).

Insider Tips
Save room for dessert! After your meal, walk one block toward the Arno River (on the same street as Dante’s) and you’ll find the best gelato in Florence the world. Gelateria La Carraia is disgustingly delicious, and doesn’t have any of the artificial colors or unnecessary add-ins that tip you off to a tourist trap.

Dinner Date (First Class)

Il Palagio – Four Season Firenze

Borgo Pinti, 99, Florence, Italy 

Dress: Elegant Casual – there’s no dress-code, but why not take the opportunity to bust out the fancy dress and sharp suit you packed?

Price: $$$$ – Il Palagio* has one of the coveted Michelin Stars, a sign that it is recognized at a top restaurant worldwide.

Bonus Tip: If you happen to be in Florence in the warmer months, take a stroll through the hotel’s gardens. The grounds are a little slice of heaven, and, in case you’re wondering about the level of service, pashminas are offered on nights the air is a bit cool.

If there’s one thing we love to do on every date flight we take, it’s a chef’s tasting menu in the city where we’re basing ourselves. This is usually always our most expensive night out, but it’s also almost always worth the cost. Especially when you’re the type [like me] who errs toward the side of “chicken, please” when trying new cuisines. Tasting menus allow you to try expertly prepared foods that you may never have ordered for yourself, plus the excitement of being served new dishes without knowing what may come next is the perfect experience to share with your loved one. There really is no better date night than splitting a bottle [or two] of wine over the course of a multi-course tasting menu.

When spending money like this on a meal [Il Palagio’s tasting menu is €115 per person, not including wine], it’s perfectly within your rights to expect exceptional service. And every time we’ve dined at Il Palagio, the staff has delivered. Our glasses were never empty, and the manager makes it a point to personally visit with each guest in the dining room. Plus, on top of the amazing food and service, Il Palagio is hands down one of the beautiful restaurants we’ve ever seen. Seriously, if we ever come into enormous sums of money I’m going to model my house after the Four Seasons in Florence.

Insider Tips

Towards the end of the meal, you may be asked if you’d like to try some chocolates. Say yes. The cart they’ll bring around literally carries a tree trunk made of chocolate, to be shaved off tableside for you to taste. To be honest, I have no idea how much this added to our final bill, but it seems like a good rule of thumb to say YES when asked if you’d like to try a piece of a chocolate tree.

Have a favorite place in Florence we missed out on? Been to any of the locations mentioned above?

Let us know in the comments section!

Coming soon!

Date Flights is a travel blog for couples – providing first-hand date ideas in cities all over the world. Whether you’re looking to splurge on an indulgent night on the town (First Class), or spend a relaxed & budget-friendly night over a casual bottle of wine (Economy), date flights has a romantic suggestion just for you.

Hoping to launch in Spring 2016, we are currently chronicling our recent trips to Brussels, Edinburgh, Florence, London, New York, Paris, Reykjavik, Rome, and San Juan.

Even more excitingly, we’re looking to start booking our trips for Winter 2016 and 2017 – if you’d like your restaurant, bar, hotel, [tour, museum, etc.] to be featured, please email us at:

We are always happy to have you along as a third wheel on our dates, and can’t wait to share our experiences with you soon!

-Erica & Mike