Nightlife in Old San Juan
Old San Juan/Puerto Rico Tourism Company

When it comes to island getaways, Puerto Rico is one of the Caribbean’s best-kept secrets. Almost the same size as the state of Connecticut, you could cross the island in just six hours. Yet despite its size, each part of Puerto Rico has its own personality. The north sports some of the Caribbean’s best golf courses, while Rincón in the west is known for its more rustic side with killer surf spots and campsites. Then comes cultural darling San Juan with its old town lined with iconic blue cobblestoned streets, Spanish forts and colonial-style architecture. Pair all of that with a booming culinary scene, five-star hotels and nearby natural attractions and San Juan makes for the perfect Caribbean getaway — minus the price tag and passport requirements of neighboring islands. Here’s how to eat and drink your way around San Juan, while throwing a cultural attraction or two in along the way.

Puerto Rico has made a name for itself in the culinary world with its mix of Taíno, Spanish, and African cuisine served up in traditional and more globally inspired styles. At Oceano, which was featured on the Food Network, the sleek three-story oceanfront restaurant in Condado has a menu of Puerto Rican favorites like mofongo, a fried plantain-stuffed dish, with gourmet spins adding in shrimp and passion fruit reduction (dishes range from $18 to $36). The more casual Parrot Club in Old San Juan is perfect for lunch with its breezy courtyard-style space and twist on Latin favorites like nachos with ropa vieja (stewed beef) and Cuban black bean croquetas ($8-$12). Of course you can’t leave Old San Juan without visiting the nearby Barrachina, whose claim to fame is being the birthplace of the piña colada. Known for its buzzy nightlife scene, Old San Juan looks completely different come nightfall. Here you can find everything from tequila bars to speakeasies, with one of the local favorites being La Factoria, known for its hidden rooms and bartenders that whip up craft cocktails so good, they’ve helped the spot snag a place on the 2015 list of the World’s 50 Best Bars.


A must-visit while in Puerto Rico, El Yunque is the only subtropical rainforest in the United States Forest System, and just a 45-minute drive from Old San Juan. The rainforest has a variety of trails from easy to more challenging treks that could take anywhere from a half- to a full-day trip. If you have time to spend, head to Juan Diego Falls and the stone Mt. Britton Tower for panoramic views. For those on a time crunch, the popular La Mina trail takes about an hour, with the halfway point, La Mina waterfall, being the main attraction. In winter, this spot fills up fast, so hit the park when it opens at 9 a.m. to skip some of the crowds. With only six bioluminescent bays in the world, Puerto Rico happens to be home to three of them. Come nightfall, head an hour from San Juan to Laguna Grande for a two-hour kayak tour through the mangroves into the bioluminescent bay that lights up like stars as you paddle through the dinoflagellate-filled water.


Start your tour of Old San Juan at the Castillo San Cristóbal, a fort at the eastern gate of the walled city built in 1634 to protect against enemy attacks on land. Spanning 27 acres, San Cristóbal not only shows off some of Puerto Rico’s history as the spot where the first shots were fired during Spanish-American War, it also offers sweeping views of the coastline, Condado and Old San Juan. Afterward, head to Old San Juan’s blue cobblestoned streets lined with jewel box-colored colonial buildings home to local restaurants and boutiques tucked between the souvenir shops. One standout is contemporary concept shop Luca, with handpicked (and handmade) jewelry from local designers. Concalma is another design savvy shop known for its locally made upcycled denim totes. For travelers more into big-name designers, make your way to the chic Condado neighborhood where you’ll find a slew of boutiques like Cartier, Gucci, and Louis Vuitton.

The InterContinental Ocean View Room
The InterContinental

If it’s beaches you’re after, the 397-room InterContinental San Juan is sitting on one of the best in the resort-heavy area of Isla Verde. Fresh off of a $22 million renovation, the 15-year-old hotel has all the makings of a five-star Caribbean beach resort, with ocean view rooms starting at just $160. Located on a 2-mile stretch of white-sand beach, you’ll find everything from beach attendants setting up your lounge chair (complimentarily, of course) to a lagoon-inspired pool, as well as six restaurants, and an after-hours bar complete with a firepit. If want to up the luxe factor even more, the Club Level suites are set right by the pool and spa and include perks like private check-in, as well as complimentary breakfast, snacks, and cocktail hour in the lounge (rates for a king start at $240 per night). While you could hole up here the entire time spending your days by the beach, a trip out to Condado or Old San Juan is just 20 minutes away.

For something a bit funkier, the 32-room boutique CasaBlanca Hotel on the Calle Fortaleza is tucked between the restaurants, bars, and shops of Old San Juan. One of the tallest hotels in the area, you can catch rooftop views over San Juan from the Moroccan baths perched on the sundeck, perfect for a soak after strolling these streets all day. Décor sticks to a Moroccan-meets-European theme (think flowy white netting over beds, pop art paintings, and antique French and Spanish furniture) that starts as you walk inside the Spanish courtyard that doubles as a lobby, with a 12th-century Spanish chandelier cascading overhead. Rooms start at $109, and keep in mind that since the building is a walk-up, there’s no elevator.

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