If you haven’t yet been to Tulum, chances are your well-traveled coworker (or yoga instructor, or dog walker) has. The Mexican beach town on the Yucatán Peninsula is now known as much for its raucous nightlife and wellness community as it is for its ancient Mayan ruins. If you’d like your next getaway to be a little more stress-free, head east to San Juan, Puerto Rico.
The Caribbean island and U.S. territory has lively beaches, boutiques peddling handmade jewelry and vintage straw hats, cocktails mixed with locally grown fruit and herbs, and beachfront kiosks hawking salty octopus fritters. It has all of the vibrant culture and laid-back appeal of Tulum—but with far fewer crowds (and DJs). Plus, there’s no passport required.
Here is a primer on where to stay and what to eat, drink, and see on the Isle of Enchantment.
Where to stay
Originally built by the Vanderbilt family (and designed by the same architectural firm responsible for New York’s Grand Central Terminal), the Condado Vanderbilt celebrates its centennial this year. The historic, oceanfront property maintains its air of old-school sophistication and service while also offering modern amenities like pool and beach butlers who can deliver a steady stream of fruity frozen cocktails to your deck chair, a wood-paneled and marble spa with a Turkish bath, and meals with a focus on local ingredients. (For breakfast, try a cold-pressed juice, farm-fresh eggs with house-cured salmon, and guava pastelillos made by the pastry chef.)
Tucked away on a cobblestone street in Old San Juan, El Convento is a former Carmelite convent that dates back to 1646, now with luxury suites, a daily wine and cheese reception, and an outdoor plunge pool. The charming, open-air courtyard—with a nispero fruit tree growing at its center, greenery spilling over the sides of balconies above, and umbrella-topped tables—is the perfect spot to sip local coffee in the morning and return midday for a cocktail, made with herbs and fruit grown in the on-property garden.
What to do
When you visit Castillo San Felipe del Morro, located on the northwestern point of Old San Juan, chances are the sprawling lawn leading up to the 16th-century Spanish fortress will be peppered with families picnicking and flying kites. Take a few minutes to soak in the scene before climbing to the top of the Unesco World Heritage site for panoramic views of San Juan Bay.
Afterward, spend an afternoon wandering through the alleyways and streets of the historic district, taking in the colorful Spanish colonial architecture and stopping for a refreshing tropical fruit ice from one of the ubiquitous street carts. Beaches in Condado and Isla Verde are beautiful and convenient if you’re staying in the area. But don’t miss Piñones, located on a stretch of Route 187 on the northeast part of the island, for the roadside kiosks selling deep-fried bacalaítos and alcapurrias (fritters made with cod or plantains and ground beef, respectively)—all with the same sweeping ocean backdrop.
For a day outside San Juan, head about 40 minutes west to the family-run farm Frutos del Guacabo to taste tamarind and tomatoes, pet rabbits and goats, and learn about its mission to make Puerto Rico less dependent on imported foods. (Contact the farm to arrange a tour.)
In Santurce, visit the Museo de Arte de Puerto Rico for a look at works by local artists dating back to the 17th century, then stroll the streets outside to see public art. The neighborhood is known for its vibrant, larger-than-life mosaics and murals.
What to drink
The piña colada was invented here, but with all due respect to the boozy tropical drink, Puerto Rico’s cocktail culture has far surpassed that claim to fame. That La Factoria—with its skilled bartenders and perfectly executed cocktails—has been named one of the world’s best bars more than once won’t surprise you in the least. That it maintains an intimate vibe and warm, unpretentious service just might. (The bar doesn’t have a sign, so look for the building on the corner of San Sebastián and San Jose streets.)
A few steps away, La Taberna Lúpulo offers 50 beers on tap, some from local breweries like Zurc Bräuhaus and Ocean Lab. (The latter is open for tours of its Isla Verde–neighborhood brewery.) In La Placita, Jungle Bird serves nuanced, Caribbean-inspired cocktails—made with local ingredients like passion fruit, coconut cream, and hibiscus—out of tiki glassware with tiny umbrellas. Nearby, El Bar Bero seamlessly transitions from barbershop by day to cocktail bar by night, and hair-themed drinks like the Mullet, made with citrus vodka, elderberry, and house-made blackberry preserves, prove just as smooth.
What to eat
While upwards of 85% of Puerto Rico’s food is imported, approximately 75% of the ingredients on the plates at 1919 Restaurant come from the island. Chef Juan José Cuevas returned to his homeland after working at restaurants like the Michelin-starred Blue Hill in New York City, bringing his expert technique and passion for working with local farmers to dishes like chayote salad with goat cheese, and handmade pasta with arugula-pistachio pesto and pickled ají dulce (sweet pepper).
Other fine-dining options include Marmalade, in Old San Juan, with its award-winning wine list and a white bean soup with black truffle oil and pancetta dust that has a cult following, and Vianda, in Santurce, run by husband-and-wife duo Francis Guzmán and Amelia Dill. The eclectic, seasonally changing menu highlights local produce and gives a nod to traditional Puerto Rican recipes, while also infusing global flavors into dishes like tempura-fried pumpkin and squash with pique aioli and Tom Kha cod with local coconut.
Also in the Santurce neighborhood, 16 food kiosks make up Lote 23, including Hen House with buttermilk- and pickle-brined fried chicken sandwiches, and an outpost of artisanal pop shop Señor Paleta. (Try the bright fruit juice flavors like tamarind, or creamier options like Nutella.) Join the stylish crowd at Sabrina for brunch as flavorful as it is photogenic, and Café con Cé for coffee made with locally grown beans, both on Calle Loiza. The Mallorca Jamón y Queso—a sweet roll filled with ham and cheese and dusted with a thick layer of powdered sugar—at neighborhood diner-bakery Kasalta makes for a memorable breakfast or lunch.
More must-read stories from Fortune:
—Where you should eat, visit, and stay on your trip to Copenhagen
—This island in Washington State will make you feel like a multi-millionaire
—Why you should visit southern India on your next vacation
—Inside the “ultimate high-performance luxury lifestyle” experience at the new Equinox Hotel
—Listen to our new audio briefing, Fortune 500 Daily
Follow Fortune on Flipboard to stay up-to-date on the latest news and analysis.
Sign up for the Fortune Features email list so you don’t miss our biggest features, exclusive interviews, and investigations.
