Infinite Legroom

What To Do With 48 Hours In San Juan​, Puerto Rico​

A plethora of places to hit up, drink, party and play

Puerto Rico is a perfect escape from the U.S., with many perks for a stunning vacation — beautiful beaches, delicious food and a shot of Latin culture. Bonus for Americans, you don’t even need to bring your passport or even worry about currency exchange, as your US Dollars are accepted here. While we’re sure you can find information on San Juan pretty easily, with a plethora of places to hit up, drink, party and play — we’re all about getting off the beaten path for something a little different. 

We experienced a whirlwind weekend trip here a few weeks ago and spent our first visit to Puerto Rico exploring a bunch of different areas in San Juan. If you are heading to the island and want to get a fix for what’s happening and what’s beyond the tourist areas, here’s a few things we recommend to set you in the right direction. From three different choices for a place to lay your head, the best of breakfast, lunch and dinner and even some outdoor activities if you feel inclined… sit back and check out our 48 Hours In San Juan, Puerto Rico Guide.

Stay In A Designer B & B

Hotels are amazing, but some of you may be after something a little more unique and lower on the budget — without sacrificing style. This incredible multi-room guest house is located in a gated community only 10 minutes drive from the airport. Created by an ex-movie set designer, it’s eclectic touches will have you feeling like you really escaped from the city. Group kitchens, vegetarian meals cooked by the house chef and even yoga classes twice a week. This is a retreat for those who want to add R&R into their world.

For more about the inspiration behind this stunning guesthouse, click here.

2009 Calle España,
Ocean Park, San Juan
Puerto Rico, 00911

Image credit: Dreamcatcher Guesthouse

A Luxury Choice

Luxury lovers unite. The Ritz Carlton, located in the Isla Verde area is super close to the airport, so within 15 mins of landing you can have your feet in the sand and a Piña colada in hand. It’s got a beautiful pool and bar area where the staff are always ready to shield you from an afternoon shower or bring you ice cold drinks until the sun sets — the Ritz Carlton sure plays on it’s superior service in lush settings. The beach is gorgeous too, with plenty of chairs and umbrellas with exclusive use for hotel guests. There’s also pretty amazing sushi in the lobby bar, which is a nice change from the more traditional island fare.

Ritz Carlton San Juan
6961 Avenue of the Gobernadores,
Carolina, Puerto Rico 00979

Image credit: Sarah McLellan

New + Improved

On another side of San Juan in Condado, you’ll find the newly renovated San Juan Marriott and Casino boasting rooms with incredible views of the turquoise water and white sand beaches below. When you arrive in the sleek lobby, a bonus for tech savvy travelers allows you to check in via their Marriott app and skip the lines. Lots of activities and things in the neighborhood to keep you occupied, but our guess if that you’ll be laid out by the pool with a swim up bar. A bonus here is the hotel restaurant, La Vista Latin Grill, where we ate a delicious Octopus Carpaccio and Churrasco steak with “Mamposteao” style rice and beans. Delicioso!

San Juan Marriott
1309 Ashford Ave, San Juan,
PR 00907, Puerto Rico

image credit: Sarah McLellan

Health + Wellness

For some local flavor and in an area yet to fully realize it’s potential, is the Kamoli Kafe which offers health conscious fare for those who want to keep things light in the am. Fresh squeezed juices, salads and a variety of sandwiches await you at this cafe and boutique mix. The staff is friendly and ready to arm you with a list of other local recommendations, complete with hand drawn maps and service with a smile. A favorite here is the banana-honey-milk pancakes and we’d have to agree.

Kamoli Butik & Kafé
1706 Calle Loiza,
San Juan 00911, Puerto Rico

Image credit:

Namaste Session

For those who wanna get their OM on after breakfast, this Ashtanga yoga studio is set up right along the main thoroughfare of Calle McLeary, where you can head upstairs for a class with one of many expert teachers. Once finished, you are literally a 5 min walk down to the beach inside Ocean Park’s gated community where you’ll find more locals vs tourists and tons of space to throw down and towel and relax in front of the waves.

Ashtanga Yoga Puerto Rico
1950 Calle McLeary,
Ocean Park, San Juan, PR 00911​

Image credit:

Happy Hour Margaritas

Did someone say Fish Tacos and cold Margaritas? Yes, please. This is another local spot with good flavors and a friendly staff that will give you some local tips if you care to ask. We loved the fish tacos, classic margaritas and also their house hot sauce, spiked with a serious amount of chilies. Definitely add this to everything you eat here, including straight up on their whole fried tortillas. Check out this spot too for happy hour in the afternoon. Who doesn’t love a cheap Marg after a day in the sun?

La B de Burro
2000 Calle McLeary,
San Juan, 00911, Puerto Rico

Image credit: Sarah McLellan

Paddleboarding At The Lagoon

SUP, no seriously, stand up paddleboarding is a sport to reckoned with and if you are after some action, the Condado Lagoon is the site where Velauno offers classes and on the water workouts. Prices start at $20 for a one hour session Monday through Sunday. During the week they have a great deal for $35 which gets you two hours on the water. Get those abs ready, this is hard-core.

Paddle Boarding
860-898 Ashford Ave.
San Juan, PR 00907

Image credit:

Old San Juan

A walk around San Juan’s historical Old Town is a must and you will find yourself getting lost through the winding cobblestone streets and up the hills to the forts and views of the ocean below. Old San Juan can get packed with tourists when the cruise ships come to port, so we’d recommend staying away during that time. Make sure you get some panorama shots up on the hill, your Insta pics won’t quite do it justice.

Image credit: Sarah McLellan

Eat High End Local Food

Another great spot to visit, especially for food and drinks is La Placita, the site of many day time markets and night time party. Head here during the weekend nights and you’ll find hundreds of locals and some in the know tourists here drinking on the streets, dancing and generally having an amazing time. A couple of awesome restaurants are right here for your enjoyment including the local seafood fav Tasca El Pescador, serving amazing seafood, grilled specialties and our favorite, the squid ink risotto.

Around the corner and probably with a long line out the door is Chef Jose Enrique’s self named restaurant Jose Enrique on Duffaut St. He was named one of Food and Wine Magazine’s Best New Chef’s last year and was the first Puerto Rican to get that accolade. His daily menu changes and features the bounty of Puerto Rican produce and fresh seafood and meats. It’s a must stop if you want a high-end yet comfortably casual eating experience in San Juan.

Image credit: Food and Wine/

Speakeasy Cocktail Bar

One thing you should definitely do while you are in town is hit the speakeasy cocktail bar, hidden in the winding streets of Old Town. This cocktail bar – restaurant – club is like a labyrinth of new cool in an otherwise tourist heavy section of town. Enter on the street through a unmarked door, enjoy what looks like the only space in the bar, yet walk through the wooden doors to the side of the bartender and you are in a whole other room with another bar. The same goes for when you continue through the back, you’ll find more spaces offering food and finally the back room which turns into a dance club with DJ’s as the night moves into the later hours. Be sure to order the Lavender Mule or hit up one of the bartenders to shake up a favorite of their choice.

La Factoria
Calle San Sebastian #148
00901 San Juan, Puerto Rico

Image credit:
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