Whether you’re island hopping or looking for a quick tropical getaway, Puerto Rico is making a Caribbean comeback. With its trending hotspot of Condado and alluring historical charm, the city of San Juan should be on your radar right now. Here’s a quick capital city adventure where you’ll discover Old San Juan by day and the new San Juan by night.
Stop One – Get Established
Where: Cafe Mallorca
Why: Make Cafe Mallorca your first stop in Old San Juan. It’s a local establishment that houses the quintessential Puerto Rican pastry known as a Mallorca. Approach the counter and order this sweet, buttery bread, topped with powdered sugar and stuffed with any combination of ham, cheese and egg. Or mimic the purists and stick to it plain alongside a café con leche, while you enjoy all the diner-style action from your red vinyl stool.
Stop Two – Cobblestone Culture
Where: Streets of Old San Juan
Why: We highly recommend leaving the map folded and letting yourself get lost among the 7-square-blocks of colonial architecture and brilliant colors of Old San Juan. Dating back to the 1500s, it’s truly a magical experience to explore a city confined by medieval fortress walls. From the plazas to the photo-op sentry boxes dotted around, you’re in for a cultural experience on foot.
Stop Three – Tapa Time
Where: Hotel El Convento
Why: Cocktails and tapas in a breezy, Barcelona-like courtyard will have you lingering at Hotel El Convento. Once a convent for Carmelite nuns (for 252 years) then a dance hall, this gem has been superbly resurrected as a famous institution. The elegant, open-air patio is the perfect place to share mini piononos with agave nectar margaritas.
Stop Four – History With A View
Where: Fort El Morro
When: 1 pm
Why: Stepping through the 400-year-old fortress walls, you will get a glimpse of what it was like to guard a city against seaborne invaders. A multi-level promontory built with triangular stairwells, this World Heritage Site is not to be missed. From the upper level there are grand views to the west over the Santa Maria Cemetery.
Stop Five – Shoreline Stroll
Where: The City Walls
When: 3:00 pm
Why: Leaving El Morro head west towards the shore to find a lovely trail that will wind you along the city walls down to the San Juan Gate, Governor’s mansion “La Fortaleza” and Raíces Fountain. Afterwards pop into nearby Luca on Cruz Street for locally designed jewelry – think modern chic, not knick-knack. If trendy is not your thing, check out Olé for a classic, customized, handwoven Panama hat.
Stop Six – Refuel Local Style
Where: Birra y Empanadas
When: 4 pm
Why: Continue down Cruz Street to the hip eatery Birra y Empanadas, AKA beer and empanadas – need we say more? Since you have undertaken a day of binge eating, why not try a healthy selection of baked empanadas dipped in a variety of homemade sauces, from avocado to tamarind. This pit stop is a quaint, casual place to grab a cold Medalla beer and your wallet will feel quite loved too.
Stop Seven – Siesta? Sangria.
Where: Casa Lola
When: 5 pm
Why: To ramp up your buzz, head over to Condado, a new district right outside of old San Juan. The cute, pink house of Casa Lola screams authentic Puerto Rican flavors with its menu of mofongos, a famous fried-plantain based dish. We have to say the rum punch sangria will put a bounce in your salsa step if you decide to hit the town tonight.
Stop Eight – Foodie Fight
When: 7 pm
Why: Steps from the beach in Condado and above the high-end shops of Ferragamo and Cartier, you will find this exotic oasis headed by esteemed Chef Robert Trevino. Where Asian fusion meets local cuisine, you will embark on a culinary adventure from plantain pork dumplings with shaved truffles and halibut carpaccio in sweet coconut milk to duck pad thai. The uncontrollable flavors will leave you wanting more.
Stop Nine – After Dinner Glam
Where: Condado Vanderbilt
When: 9 pm
Why: For more panache in Puerto Rico, visit the newly reopened Vanderbilt. It’s vintage glam decor takes you back to the 1920s when royalty roamed around this legendary hotel. Enjoy a glass of red accompanied by a soft tune played by piano man Mr. Escobar to ring in the evening, before heading home to your luxury pad to relax and recover.
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Photographs: Lacy Colley; Shutterstock