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.


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