Photos and Words by Rheanna Martinez

A colorful city full of street art, rhythmic music, tropical beaches, and people-watching on a beautiful island with rain forests and bioluminescent 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 day job, rent an airy loft with perfectly crumbling paint, and spend your days in a balcony hammock staring out over the Caribbean waters with a Puerto Rican coffee in hand.

Open air lofts in Old San Juan

Where to Stay

The 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, arranging door to door service, and to top it off — offering free drinks at area hangouts. Bring out your inner child with the outdoor water slide and swim-up pool bar. Get a massage in the spa, or on the beach. Sleep with your windows open to the sound of the coqui frog, and wake up to an incredible high-rise view of the early sunbathers below. Spend mornings lounging with delicious breakfast, unlimited mimosas, and friendly beach service. When the sun starts to set — grab a cocktail at the beachside bar, then head to the posh lounge for live salsa music. And when you’re still looking for more fun — wander into the casino. If that hasn’t sold you, the staff might be some of the most friendly, accommodating, and beautiful people we’ve ever encountered.

Villa Herencia: If you’re looking for something a bit more quiet and intimate in Old San Juan — consider Villa Herencia. A former haven for nuns, this eight-room boutique hotel is found by wandering down a light-filled alleyway around the corner from a legendary cathedral. The rooms are each uniquely decorated, with luxurious tubs, billowy lace curtains and carefully curated accents. There’s an air of romantic charm here, 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 plantations just an hour away. Sit an 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, and you’ll miss out on the long evening lines.

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 the 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. So is the octopus. And you must absolutely save room for dessert. Trust us.

Guavate Lechoneras: This is best saved for a Sunday, the only day you’ll find these. If you want to push your more adventurous food side and go beyond the beaches and tourists into the mountains — this is your calling. Once you arrive on the tiny mountain road, you’ll be greeted with dozens of small, open-air restaurants, each with a succulent pig roasting and locals as the only patrons — drinking, laughing, and dancing to the band made of up neighbors from up the street.

View over the haunted lookout point

Where to Play

WOW Surfing School: Treat yourself to a surf lesson in the mild waves of Playa Isla Verde. It’s harder than it looks, so be happy you started on a beach where you can also drink mojitos and lay out in the sun.

Acampa Adventures PR: Schedule a pickup for a full-day adventure in Toro Negro, the island’s highest rainforest reserve. You’ll hike coffee plantations, climb up and then rappel down through waterfalls, zip line high above the rainforest, and dive into 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 an icy drink. Explore the forts and old ruins. Drink a mojito at Marilyn’s, where a cat is your bar mate. Feed the pigeons. And dance to the old men playing guitars in the square.

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.

Take me back.

Isla Condado
Surfing on Isla Verde.
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