San Juan is the rare city that tempts art lovers, history buffs and beach bums in equal measure. This is a Caribbean destination for culture lovers, a vivacious urban enclave steeped in colonial history and chock full of romantic hideaways, vibrant local art, a fresh take on traditional Puerto Rican cuisine and dramatic ocean views.
This place has captured the imagination of adventurers since Christopher Columbus landed here in 1493. Hundreds of meticulously restored colonial buildings from the 16th and 17th century, painted in cheerful shades of tangerine, aquamarine, lemon, rose and mint, still stand proudly along the blue cobblestone streets of Old San Juan and welcome travelers to one of the oldest continuously inhabited European settlements in the U.S. and its territories. The stone walls that enclosed the city when it was Spain’s most strategic military outpost in this part of the Atlantic still keep watch.
San Juan is every bit as beguiling now as it was then. To make the most of a weekend jaunt, skip the museums and immerse yourself in the sights and sounds of San Juan at street level, drinking in the city’s art, food, architecture and scenery as you stroll in the sunshine.
Looking for your perfect San Juan stay? Check out our curated selection of Room with a View: The Best San Juan, Puerto Rico Hotels.
Art of the Hotel
For an eclectic mix of historic elegance and eye-catching art, book a room at the CasaBlanca Hotel on Calle Fortaleza, a lushly comfortable retreat nestled in the heart of historic Old San Juan. The boutique style hotel offers 32 rooms, each uniquely decorated with antique wood furniture, colorful art created by Puerto Rican artists, richly layered textiles and gauzy white canopies billowing from atop the bedposts. Guests enjoy 24-hour access to a rooftop terrace with lounge chairs, stone soaking tubs where the water temperature can be customized to help occupants achieve optimum relaxation and a bird’s-eye view of the old city and the ships in the bay.
Art of the Meal
The restaurants in SoFo (South of Fortaleza Street in Old San Juan) get a lot of buzz, thanks the plethora of dining options in the neighborhood and the SoFo Culinary Fest, but there are intriguing restaurants in all over town. Puerto Rican chefs are having fun riffing on the island’s culinary legacy and spinning it into something new.
This is humble and hearty food jacked up with fresh, colorful garnishes, rich and tangy sauces and a penchant for all things savory, salty and fried to crisp, golden perfection. Look for the traditional root vegetables (cassava, yams, squash and plantains) that have graced the island’s tables for centuries, as well as just-caught seafood, rice and beans (which are plump, pinkish red and called habichuelas here) and lovingly prepared pork dishes.
Café Fortaleza (located on the street of the same name) is a good place to start exploring local food. It offers stylishly presented entrees and classic Puerto Rican sides like tostones de plátano (plantain) and plenty of mayo-ketchup for dipping. (Made with a blend of ketchup, mayonnaise, garlic and spices, it just might be the island’s most addictive condiment.) The menu rotates, so look for other favorites, including upscale versions of classic beach foods like bacalaítos (crispy codfish fritters) and stuffed fritters called alcapurrias.
Speaking of the beach, don’t miss El Ambique Beachfront Bar and Grill, located just steps from the white sand of Isla Verde Beach. It gets busy (and loud!) as the sun sets, so go early or explore the turquoise water and wide beaches before (or while!) you wait. The seafood is superb (the menu features options like mango ceviche, sweet chili beer battered shrimp and lobster stuffed tostones) but this seaside spot also offers vegetarian options and a particularly good mofongo. This dish —a combination of mashed plantains, pork cracklings and a protein like chicken, steak or shrimp — is a Puerto Rican specialty. You’ll find it all over the island.
To get off the tourist trail, check out Soda Estudio De Cocina, a funky neighborhood joint in Miramar. If you’re as tempted by egg rolls and fajitas as you are by pork belly and Mac and Cheese, this spot is for you. The cheerful mash-up of Caribbean, Asian, Mexican and Spanish cuisine is served (mostly) tapas style. Try a blackberry mojito from the cozy little bar or order from one of the better craft beer lists in the city.
Art of the Drink
Puerto Rico produces a lot of rum (ron in Spanish) so don’t leave the island without raising a glass of Palo Viejo, Ron del Barrilito, Ron Llave, Don Q or Bacardi. Try it in your favorite cocktail or do what the locals do and ask for a chichaito – a shot made with anise-flavored liqueur and white rum
Prefer something sweeter? Try a piña colada. The classic umbrella drink, which blends rum, pineapple juice, and coconut cream, was created in San Juan, although purists still debate if this momentous moment in cocktail history happened at Caribe Hilton or Barrachina Restaurant. The discussion about which version is superior is equally intense. The only responsible thing to do is try them both, right?
Art of the Outdoors
No trip to Puerto Rico is complete without a beach day. San Juan offers lots of easily accessible urban beaches, but to maximize outdoor fun both in and out of the water, check out Balneario El Escambrón, It’s located within walking distance of Old San Juan and the bustling Condado dining, entertainment and hotel zone. The beach offers access to oceanside and park trails that are popular with cyclists and joggers, palm tree shaded sand for strolling and relaxing, as well as swimming, snorkeling and scuba diving spots protected by a coral reef.
Art Of The…Well, Art.
To experience the art, history, and architecture of Old San Juan, just pull on your shoes and start walking. (If walking’s not your thing, there are also free, handicap-accessible trolleys that circle through Old San Juan daily. Hop on and off at any numbered stop and avoid Stop 1 when cruise ships are in port.)
Start at the Paseo de la Princesa, an oceanfront promenade that offers gorgeous views of San Juan Bay and an up-close look at the thick stone walls that protected the city for centuries. Get a photo of Spanish artist Luis Sanguino’s “Fuente Raices,” a fountain symbolizing the native Taíno, African and Spanish roots of Puerto Rico before strolling the shaded walkway to the Puerta De San Juan or San Juan Gate. When this doorway was constructed in the 1630s, it kept invaders out. Now it welcomes travelers into Old San Juan.
Take a left to see “La Rogativa,” a bronze sculpture by New Zealand artist Lindsay Daen. It commemorates the women who took to the streets to petition God for mercy during a siege of San Juan in 1797 and wound up thwarting the invasion.
Continue northwest toward Castillo San Felipe del Morro (El Morro), an impressive six-level fort that’s guarded Puerto Rico since the 1500s. This UNESCO World Heritage Site gives you a chance to walk in the footsteps of the men stationed there. You can peek out of the sentry boxes that have become a symbol of San Juan, descend the steep stone steps and see just how small you needed to be to operate a cannon.
Need a break? Find a vendor nearby if you want to join the crowd and fly a kite in front of El Morro. Or stop by nearby the Plaza del Quinto Centenario (Quincentennial Square) to see “Totem Telúrico” by Puerto Rican artist Jaime Suarez and join the kids for a splash in the walk-in fountain. Further east, rest in the tiny, shaded Plaza de San José at the feet of Ponce de León, the Spanish explorer and first governor of Puerto Rico. His likeness is sculpted from British cannons captured in a raid, which is weirdly appropriate for a conquistador.
The final stop is Castillo San Cristóbal. Like El Morro, this fort (and its sprawling ramparts and hidden tunnels) is part of the U.S. National Park Service’s San Juan National Historical Site. For one of the prettiest views in the city, walk up the curving ramp to the top of the fortress and look out at the candy-colored colonial buildings of Old San Juan, with El Morro in the distance and the crashing waves of the North Atlantic as far as you can see. You’ll have taken in hundreds of years of art, architecture, and history in a single glance.
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