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! 


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