Get Your Bearings Port locations: San Juan Cruise Port is set within San Juan Bay near Old San Juan. It’s about 15 minutes drive from the international airport. Destinations: Aruba, Bonaire, Curaçao, Antigua, Barbados, St. Lucia Cruise lines: Carnival, Celebrity, Royal Caribbean, Holland America, Norwegian, and many more |
The San Juan Cruise Port in Puerto Rico is located in the middle of Old San Juan, steps away from restaurants, attractions, and architectural finds. When you exit the cruise terminal, you’ll be on Paseo Gilberto Concepción de Gracia, a waterfront walkway. Turn away from the water and head uphill to find yourself in the middle of the 17-square-block neighborhood known as Old San Juan. A popular first stop is the San Juan National Historic Site, consisting of two waterfront forts that are relics from Puerto Rico’s past as the gateway to the Atlantic trade route. You’ll also find plenty of places to shop for local art and options for trying mofongo along Calle de la Fortaleza. A classic end to a first day here includes drinks at Eter Rooftop & Lounge with sunset views over the San Juan Bay. Welcome to Puerto Rico!
San Juan in a day
Many ships arrive around 7 a.m. and you’ll need to get going early to get the most of out one day. Get your morning coffee fix at Don Ruiz Café, a fourth-generation roaster located inside a traditional Spanish style courtyard, across the street from the hilltop fort, Castillo San Felipe del Morro, and about a 15-minute walk north from the cruise port. The guaritas, sentry boxes, positioned throughout were used to keep watch for enemy ships and have become emblematic of the island as a whole. A second fort, Castillo San Cristobal, is within walking distance and included in your admission.
After learning about maritime defense, switch sails and have a chocolate-themed lunch at Chocobar Cortes. This beloved brand has been manufacturing farm-to-bar chocolate for nearly 100 years. Chocolate is incorporated into the menu items, like the Chocoburger with chocolate ketchup or smoked pork wrap seasoned with a chocolate rub. To take a taste of the island home with you, stop by Montadero Chocolate’s new location in Old San Juan. They are locally and family owned and offer hand-painted bonbons with Puerto Rican flavors like passion fruit, dulce de leche, and even Bacardi.
In the afternoon, walk off your meal by strolling the cobblestone streets. To support local artists, stop by the Poets Passage and see if there’s an open mic night while you’re visiting, or admire the various artworks of differing media inside Gallería Botello. Don’t miss the Catedral de San Juan Bautista, the second oldest cathedral in the Americas dating back to 1521.
Head back to your ship via Paseo de la Princesa, a pedestrian promenade, and change for dinner. When you’re ready, Marmalade is a short walk away and ideal for celebrating special occasions with a tasting menu of four to six courses. The white bean truffle soup and lobster risotto are standout dishes. For a more casual dining experience and chance to shop the flagship store of Puerto Rican Rums, try La Casita de Rones, a pink house near the cruise ships that’s hard to miss.
There is salsa dancing every Sunday and Monday night at La Factoria in Old San Juan, considered one of the best cocktail bars in the Caribbean. Also nearby is the Cannon Club, an eclectic piano bar with a relaxed, lounge vibe. For an LGBTQ+ friendly setting, go to La Sombrilla Rosa or El Cafetín.
If you have two days . . .
Santurce is a neighborhood adjacent to Old San Juan, adorned with community art and in the middle of gentrification, with old buildings mixed among new skyscrapers. It is the most populated neighborhood in the San Juan metro area and a chance to surround yourself with locals. Grab a bite at Lote 23, a lot turned hub where you’ll be spoiled for choice by Puerto Rican owned food trucks, part of an entrepreneur incubator program. Next door is the Bookmark, a small bookstore where you can shop titles by local authors. Visit the Museo de Arte de Puerto Rico to see immersive art installations and a 2.5-acre sculpture garden.
Treat yourself to dinner at Cocina al Fondo, helmed by chef Natalie Vallejo, winner of the 2023 James Beard Award for Best Chef South. Try the pan-fried octopus and pumpkin and goat cheese turnovers. Alternatively, chef Carlos Portela is a finalist for the same category in 2024 and owns Orujo, a singular dining experience elevating endemic ingredients over a dozen or more courses. There is no set menu: You sit and receive the mini dishes he brings out to you. Either option requires advance reservations. For a night on the town, head to La Placita, a nightlife area packed with clubs, and bars. There are DJs, live music, and people dancing in the streets.
La Concha Resort features several swimming pools, a beach, and the lively Fifty Eight nightclub which opens at 10 p.m. on Fridays and Saturdays.
Photo courtesy of La Concha Resort
Stay longer
If you’re feeling active, take a bike ride on Paseo Puerta de Tierra, a dedicated five-mile sustainable pathway that connects Old San Juan to Condado, a lively area with families, water sports lovers, and partygoers alike. San Juan Bike Rentals offers guided tours and e-bike rentals. Alternatively, go on an LED kayak night glow tour of the Condado Lagoon with Night Kayak. Otherwise, take a short ride share from the cruise port to enjoy Condado Beach. Go for a walk on Condado Beach and dine at one of the neighborhood’s many fine restaurants like Santaella for the pastelon (a plantain lasagne) or Mario Pagán Restaurant for a melt-in-the-mouth sea bass filet.
La Concha Resort is the epicenter of the party scene here, with a casino and Fifty Eight nightclub. It’s also an iconic hotel known for its Perla building, a seashell-shaped architectural marvel on the sand. If your room faces the water, open the balcony to fall asleep to the sounds of the ocean.
Two places claim to have invented the piña colada: Condado Hilton and Barrachina in Old San Juan. Barrachina’s version is commemorated with a plaque outside its Old San Juan location, but the date is several years after Ramon “Monchito” Marrero, a bartender at the Hilton, is believed to have made his version. Your mission, should you choose to accept it, is to taste both and determine the true winner.
For a large choice of entertainment and dining options with no reservations required, visit Distrito T-Mobile, located by the Convention Center and a 10-minute drive from the cruise port. Barullo Taberna Española has tapas and over 20 wines from around the world on tap. La Burguesía has massive gourmet burgers that hit the spot. Arena Medalla is a sports bar dedicated to Puerto Rican athletes with pool tables, arcade games, and private karaoke rooms on the second floor. Adventure seekers will appreciate Toro Verde Urban Park, with an indoor ropes course and zip lines through the outdoor venue.
Here you’ll also find the Sheraton Puerto Rico Resort and Casino, with a rooftop infinity pool and free shuttle transporting guests to the beach and Old San Juan throughout the day.
Distrito T-Mobile has been the site of Dick Clark’s New Year’s Rockin’ Eve countdown in Puerto Rico since 2021. The event’s host (and Miss Universe 1993) Dayanara Torres told me, “I was honored to host New Year’s Rockin’ Eve. To me, it is one of the most powerful things anyone can do to represent Puerto Rico and show it to the world. There were millions of viewers—the whole world watching us. You can see our happiness, our culture, our dancing, our music—and it’s incredible.”
When asked what makes Puerto Rico special, Dayanara says, “Apart from the beauty, the beaches, the rivers, mountains, adventure—I think it’s us as people. The island is a beautiful gem, but the people take it to another level.”
