Three Perfect Days: A Trip to Puerto Rico

Where to stay

Palacio Provincial: Once home to the Puerto Rican parliament and later the country’s Department of State, this hotel is now a reimagined boutique property that welcomes visitors to San Juan. Enjoy the property's luxurious amenities and be within walking distance of popular attractions.

Things to do and see

Old San Juan: Begin at the beginning. First settled in 1509, this town rests upon centuries of history. Pastel Spanish colonial buildings line cobblestone streets that hold 500 years of memories and events. You’ll pass sites like the statue of Puerto Rico’s first governor, Juan Ponce de León, made of repurposed cannons from Britain’s failed 1792 invasion attempt.

Plaza del Quinto Centenario: Built in 1992 to celebrate the 500th anniversary of Columbus’ first sail to the Americas, this square offers striking views overlooking El Morro and the Atlantic Ocean. Visit the 16th-century Castillo San Felipe del Morro, a fortress built on the ocean’s edge, once considered impenetrable. Afterward, wander into the surrounding meadow, where a monument marks the closest the Dutch ever came to infiltrating the fortress.

Cuartel de Ballajá: Once a war barrack, this building now houses the Museum of the Americas and the fourth generation Don Ruiz Coffee Shop.

A neighborhood food tour by Spoon: Taste the flavors of San Juan by sampling food from across the city. You’re likely to receive an interesting history lesson along the way.

Souvenir shopping in Old San Juan: Pick up a map of Puerto Rico at The Poet’s Passage, try on an indigenous vejigante (mask) at Mundo Taíno or browse ceramic creations at Mi Pequeño San Juan.

Pure Soul: Shop owner Sylma Cabrera pulls together apparel from across the world for her vibrant store. Browse accessories from 200 local designers or Cabrera’s own line of vibrant linen dresses, blouses and menswear. “That’s what modern Puerto Rico is about, finding comfort where maybe you didn’t expect it,” she says.

La Factoría: Some people know it from The World’s 50 Best Bars list in 2019. Others recognize it as a party location from the “Despacito” music video. But many know the club as a maze of cavernous rooms, flowing drinks and a place to dance all night.

Where to eat

Chocobar Cortés: The 95-year-old, family-owned Chocolateria has a line every hour of the day, and for good reason. Indulge in decadent treats and, for adults, icy chocolate martinis kissed with creamy Baileys.

Hecho en Casa: This classic San Juan lunch spot has fresh-made food, cold drinks and a friendly staff.

La Taberna Lúpulo: A hidden gem, this shop knows its stuff. Try an incredible local twist on a Cuban sandwich and wash it down with a Puerto Rican beer.

1919 Restaurant: Located in the 105-year-old Condado Vanderbilt Hotel, this restaurant is run by executive chef Juan José Cuevas, the first Puerto Rican to earn a Michelin star. His philosophy is “flavor without distraction.” His dishes are crafted from goods by the country’s local artisans and farmers, using flavor and technique to redefine traditional fine dining.

Where to stay

Caribe Hilton: This hotel is the first Hilton built outside of the continental U.S. and the supposed birthplace of the piña colada. Explore 17 acres of tropical paradise, including nine restaurants, an oceanfront pool complex and beachfront access.

Things to do and see

Santurce: Immerse yourself in the city’s arts district, a sea of colors, feelings and textures.

Calle Cerra: This is a space where social commentary and culture lives along the streets. Walk along a street decorated with murals: trippy psychedelia, whimsical geometry and tributes to everyone from Spike Lee to Ismael Rivera, a legendary local singer. Discover paintings that depict playful riffs on the Puerto Rican flag and other works.

The Museum of Contemporary Art: The MAC was born from an urgency to exhibit and promote Puerto Rico’s contemporary art and its expression. The museum preserves mid-20th-century to present-day work across the Caribbean and Latin America. Its spaces and collections invite guests to pause and consider the meaning and context. Every room is a conversation between the artist and his viewers. The MAC is emotion: candid anger, fearlessness, romance, torment and vulnerability—the Puerto Rican heart laid bare.

Where to eat

Kamoli: A café and shop focused on whole ingredients and healthy eating. Try a refreshing acai bowl while looking through jewelry displays.

Bacoa Finca + Fogón: Deep into the island’s forested terrain, this community-minded restaurant sits on a lake and specializes in wood-fired cooking, playing on the Puerto Rican tradition of bonfire feasts in the woods. The chefs—Raúl Correa, Rene Marichal and Xavier Pacheco—create an unforgettable meal spiced with Carribean flavor and bawdy banter.

Where to stay

Dreamcatcher by DW: This surfer-chic beachfront spot is the only vegetarian boutique hotel in San Juan. Its exclusive 19 rooms and suites are all uniquely designed with an attached tropical terrace. Indulge in a three-course vegan breakfast or head to the 24/7 beverage and snack bar.

Things to do and see

El Yunque: This is the only tropical rainforest overseen by the U.S. National Forest Service. And at 29,000 acres, it’s one of the smallest yet most biodiverse national forests. While hiking the park’s stunning trails, look out for enormous champion trees and the tiny, once-endangered orchid that grows on their moss-covered trunks. Amble through breathtaking paths and come across striking, panoramic island views.

Mosquito Bay Kayaking Tour: After sunset, ride solo or with another to Puerto Rico’s bioluminescent bay, where microorganisms emit light when disturbed. As you paddle, watch neon blue light ripple across the water in dancing patterns.

Where to eat

La Estación: Once an abandoned gas station in Fajardo, this restaurant now merges traditional American barbeque with Caribbean flavor and style. The marriage is magical. Dine on dishes cooked over open wood-smoke fires with ingredients from local farms and waters. The experience will be unforgettable.