San Juan, Puerto Rico
A colorful city full of street art, rhythmic music, tropical beaches, and people-watching on a beautiful island with rainforests and biolumnescient lagoons. What more could you want. And you don’t even need a passport to get there. The waters are crystal clear, the history is rich, and the cobblestone streets of Old San Juan will make you want to quit your job, rent an airy loft with perfectly crumbling paint, and spend your days in a balcony hammock staring out over the Carribbean waters with a Puerto Rican coffee in hand.
Where to Stay San Juan Marriott For a classic, tried and true stay that goes above and beyond in service and ocean views - this is your place. The concierge service will help plan your entire vacation, squeezing you into booked excursions, surprising you with door to door service and free drinks. Bring out your inner child with the pool waterslides, and spend mornings lounging with beach service, start (or finish) your night with live music and salsa dancing, and for those late sleepless nights - wander into the casino.
Villa Herencia A former haven for nuns, this eight-room boutique hotel is found by wandering down a light-filled alleyway in the colorful streets of Old San Juan. The rooms are each uniquely decorated, with billowy lace curtains and beautifully adorned accents. There’s an air of old world charm straight out of a novel.
Where to eat + drink Cafe Cultura Start your morning with a coffee from this quaint coffee shop in Old San Juan. The beans are fresh from the rainforest just an hour away. Sit at one of the outdoor tables, and watch the locals dancing and laughing in the nearby square.
Fatty’s Not your classic Puerto Rican food, but damn good Jamaican and West Indian Soul Food. Go here for lunch to avoid the long evening waits.
La Taberna Lupulo When we were here, there were only 5 people in the place - and they all broke out in a harmonious melody to a romantic Spanish song. Swing in for a delicious craft beer; but arrive early to avoid tourists. Sit next to an open window, or wander to the back patio with crazy beautiful wall art and moody natural light. Luquillo Kiosks When you want to explore beyond Old San Juan and a bit closer to the beaches, venture over to these popular food stalls for a taste of local Puerto Rican cuisine - and the classic island dish mofongo. Don’t be afraid to stay a while, and have a few cheap beers with locals.
Cocina Abierta For an evening out, try this new tapas-style restaurant with a deliciously orchestrated menu and craft cocktail program. The duck tacos are amazing. And you must save room for dessert. Trust us. Guavate Lechoneras This is best saved for a Sunday, if you’re ready to go beyond the beaches and tourists of San Juan, to the mountains. Once you arrive, you’ll be glad you made the trip. Small roadside open-air restaurants roast succulent pigs on Sundays,
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and the locals are usually the only patrons - drinking, laughing, and dancing to the band - likely their neighbors from up the street.
Where to play Wow Surfing School Treat yourself to a surf lesson in the mild waves of Playa Isla Verde. Acampa Adventures Schedule a pickup for a full-day adventure tour in Toro Negro, the island’s highest rainforest reserve. You’ll hike coffee plantations, climb up and then rapel down through waterfalls, zipline across treetops, and swim in natural pools.
Old San Juan Wander the streets. People watch. Stare at the perfectly dilapidated open air lofts. Look for a door marked ‘limbers’ and treat yourself to this icy treat. Drink a mojito at Marilyn’s, where a cat is your bar mate. Bio Bay This is an incredibly romantic, magical experience best done under a crescent moon. You’ll kayak through mangroves, opening up to a bay of neon blue and a sky full of stars.
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