14: San Juan
48 Hours in Puerto Rico
Hark! My employer put me on a plane again! You know what that means - we’re back, baby. Today I’m coming to you from the idyllic reach of San Juan, Puerto Rico - a charmed business travel destination, even if just for a couple days.
I’ll be the first to say 48 hours is not enough time to do anywhere justice, but I did manage to squeeze in several things worth sharing - a testament to all the city has to offer, and to how compact and easy it is to navigate.
One key thing to note before traveling here: San Juan is a patchwork of neighborhoods, each with its own distinct character. Depending on what you’re looking for, there are several ways to experience the city. Something! For! Everyone!
Condado is Miami-adjacent with it’s high-rise, beachfront resorts and apartment buildings. Just 15 minutes down the road you hit Old San Juan - another tourist epicenter. Cruise ships dock here and eager seafarers sightsee and drink Piña Coladas inside colorful colonial buildings that date back to the 16th century when Spain colonized the island.
Stepping off the tourist track - Santurce and the sub neighborhoods within (like Ocean Park, Miramar) are home to galleries, coffee shops, record stores, boutiques and a laid back, more creative cohort of the city’s residents. I stayed in Ocean Park, the most residential of the neighborhoods listed, tucked away from the resorts of Condado and Isla Verde.
Irrespective of which neighborhoods you gravitate toward, your trip will involve beautiful beaches, incredible food and a reprieve from the hustle of the mainland.
Here’s 48 hours in San Juan > > >
Stay
We stayed at Dreamcatcher by DW Hotel - a small, eco-hotel steps away from the beach in Ocean Park. DW is a hospitality group that stands for ‘Dreamers Welcome’ and they really lean into the bohemian aesthetic. This particular property came complete with outdoor showers, hammocks strung throughout the common areas, and a perpetual fog of incense smoke in the lobby. Lean in.
They have a handful of small, design-forward concepts throughout San Juan if you rather avoid the resorts of Condado. We loved it!
Shop
There’s a creative current that flows through San Juan - from the murals covering the buildings, to the boutiques stocked with local brands, to the music that fills the streets and takes over the world (cc: Benito). There wasn’t time for a proper cultural excursion, but spending a couple of hours wandering a city is the ultimate immersion exercise. Here are some of my favorite shops and brands I sought out or encountered along the way:
Stores
Luca - high-end boutique with an 11/10 jewelry case (always my weakness).
Discotecario - record shop where the owner spent half an hour playing me old salsa records and explaining the evolution of the genre through the 60’s, 70’s and 80’s (60’s >).
Concalma - concept store that carries local San Juan brands - swiped some Conloque mugs that I love deeply.
Moni y Coli - boutique right in a buzzing little stretch of Ocean Park/Santurce by Cafe Regina (more on that below).
Designers / Brands
Hernán Herdez - gorgeous, high-end jewels.
Aida - vintage clothes + jewels. They were having a pop-up at Moni y Coli while I was there, but they do have a brick + mortar of their own.
Conloque - colorful, playful ceramics.
Isleñas - Leather footwear - snagged a pair of black sandals and once I break them in I won’t take them off.
Eat
Now for the least photogenic, but most important portion of this post: la comida. We prioritized traditional Puerto Rican food and had our fill of pernil (slow roasted pork shoulder), tostones (fried plantains), mofongo (effectively a garlicky mound of mashed plantains), meat and fish stews and fresh seafood for days.
La Casita Blanca - the quintessential San Juan spot for traditional Puerto Rican food (rumored to be a Bad Bunny favorite…). We ordered damn near everything on the menu but the fried red snapper, stuffed avocado with cod, and beef stew were favorites.
Deaverdura - authentic Puerto Rican food in Old San Juan. We had pernil (pork shoulder), rice with sweet plantains, and a sampler platter of Puerto Rico’s greatest hits, which featured bacalaítos (crispy cod fritters), tostones (fried plantains), sorullitos (fried cornmeal sticks) and others I failed to identify but thoroughly enjoyed. Extra points for the fresh coconut water. Muy bien.
Kasalta - deli/ bakery near Ocean Park. Puerto Ricans love their bread - don’t sleep on it! The place was bursting at the seams for lunch on Sunday and was a solid mix of visitors and locals. I got a Cuban (pictured below with an exquisite cheese pull) but PR is known for Mallorca sandwiches, which are breakfast sandwiches made with fluffy, buttery bread and stuffed with savory filling (eggs, meat) and dusted with powdered sugar.
Hilda Deli - part deli, part specialty grocer; dare I say, San Juan’s own shoppy-shop. Opened by the team behind Cafe Regina, another highlight of the trip referenced below, Hilda is new and trendy, and stands in contrast to the old school San Juan establishments listed above. While it’s not traditional Puerto Rican food, it is excellent. I procured one of the best sandwiches of my living life here, and if I’m lucky enough to return to PR - this might be my first stop.
Drink
This list leans more caffeination than inebriation (work trip, babes) but that’s fitting for PR given it’s history of coffee production. First, a confession - I started every day of the trip at Cafe Regina. Initially I’d planned to try a new spot every morning but all it took was one cortado with fresh cashew milk and I was… committed. So this list is brief, but I know a good thing when I see it, so why deprive myself?
Cafe Regina - I get the sense this place is a watering hole for the aforementioned cool / creative San Juan crowd. The food and drinks were excellent, as were the vibes - locals greeted the baristas by name, families lingered over breakfast and friends and neighbors gabbed as they waited in line to order. A highlight of the trip!
Habitante - stumbled on this coffee shop when I was roaming around Miramar. I had an espresso shot and a fresh ginger lime juice while observing cool locals.
La Factoría - we were told that if we could only go to one place in Old San Juan, it should be this one. La Factoría is effectively six bars in one. There’s a candle-lit cocktail lounge, a wine-focused bar, a bar with a big dance floor for salsa, a sexy little backroom lit by neon lights, and a couple more spaces I didn’t even get a chance to scope out. If you only have one night - this is the place.
San Juan is a true gem of an escape from the mainland. It’s a quick three-hour flight from NYC, no passport required, and it’s small and easy to navigate. Even in just two short days, with some work wedged in, I felt revived by my time here.
Muchas gracias San Juan, hasta la próxima.
More soon xX
the claw foot tub and the cubanooo 🤤 (and everything else)