A Perfect Day in San Juan

Any trip to Puerto Rico must include at least one perfect day in the old city of San Juan. The island overflows with a rich culture and history that you can first experience here in San Juan right after stepping off the plane. Spend a day roaming the old city, exploring cobblestone streets with hidden gems and restaurants, art galleries and shops. These are the must-see places to complete your perfect day in San Juan.

Highlights
151 Calle del Cristo, San Juan, 00902, Puerto Rico
Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.
San Francisco, San Juan, 00901, Puerto Rico
Anywhere breakfast is served all day usually scores in my book. At Caficultura in Old San Juan, the food is “farm to table” and is as delicious as the creative menu sounds. In addition to the mostly healthy options, the highlight is the maple syrup made with rum, and coconut milk–dipped french toast topped with coconut shavings. The atmosphere was pretty cool—large black chandeliers hang from large wooden beams, and the picture windows face Plaza Colón outside. Definitely a cool local place to stop into and grab a coffee or brunch while sightseeing throughout Old San Juan’s historic district.
When I first moved to the island, I joined a friend in the Old City for a tour and lesson on the history of Puerto Rico. When passing by this little section of town near Pigeon Park, my friend and native-turned-tour-guide said that this was the smallest house in Old San Juan. Wow, okay, so this little yellow portion is technically a house? I’ve visited this site several more times since then and have never actually seen anyone enter or leave this door. Whether it’s true or not, it makes for a cool story and great photo.
Calle del Cristo, San Juan, 00926, Puerto Rico
Sunny days should be cherished, and Puerto Rico offers plenty of them. Beaches are wonderful when you’re seeking to escape the heat, but Old San Juan will have you embracing the rays and feeling just as wild and free. The whole family will have a blast running around the fields of El Morro, tirelessly trying to keep a cat- or airplane-shaped kite soaring through the air. At the Plaza del Quinto Centenario, where water shoots up from the ground in foamy jets, join the locals as they gather around to frolic and cool off.
299 Avenida José de Diego, San Juan, 00909, Puerto Rico
Arts in Puerto Rico range from lavish recitals to paintings of humble local scenes. The Luis A. Ferré Fine Arts Center in San Juan puts on various performances, including theater, concerts, ballet, and opera. The center itself is a work of art, with a vibrantly-colored mural of the Muses, and a stained-glass window symbolizing the elements of nature. Meanwhile, the neoclassical Puerto Rico Museum of Art showcases visual art pieces from the 17th century onwards. Its collections feature a linoleum portrayal of a girl gathering food, and a collage in oil that depicts two faces of the famous Puerto Rican poet Julia de Burgos.
54 Calle Fortaleza, San Juan, 00901, Puerto Rico
End your day in Old San Juan with a pre-dinner stroll along the water, alongside the Old City Walls. It’s that time of day when everything seems to slow down, even the waters of the Caribbean Sea begin to ease into a glassy stillness - perfectly reflecting the midnight blue sky and the incandescent glow of the street lamps. Start from Paseo de la Princesa, at the Raices Fountain, and wind your way around the walls. Take in the views of the setting sun from the benches that line the walkway. Reminisce about the day and linger. There’s no need to rush into the night and tomorrow will come soon enough.
148 Calle San Sebastián, San Juan, 00901, Puerto Rico
Feel instantly cool when you slip through the unmarked wooden doors and enter La Factoria. Garden lights hang from the graffiti-covered walls (designed to look artsy-shabby with a stylish restraint), seductive music plays, and the liquor bottles behind the bar are lit from beneath to add to the glow. The flattering amber light in this neighborhood bar invites whispered conversations and lingering glances. La Factoria, which introduced San Juan to the craft cocktail when it opened in 2013, encourages experimentation. Take your time enjoying your drink of choice, but be sure to wander a bit further into the sprawling building where you’ll come upon separate spaces with different moods: a wine bar, a speakeasy, a dance floor.
501 Calle Norzagaray, San Juan, 00901, Puerto Rico
Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)
1552 PR-25, San Juan, 00909, Puerto Rico
A recent addition to the Puerto Rican capital’s culinary scene are food hall–style spots where diners can choose among multiple kiosks, or stalls, each featuring a distinct kind of cuisine. Lote 23 is one such spot, located in the working-class neighborhood of Santurce. More than a dozen food entrepreneurs have fare on offer here, from pizza and tacos to bao and burgers. If you just need something to cool yourself off in the tropical heat, there are popsicles and cocktails, too. The alfresco eating area has plenty of picnic tables where you can sit and enjoy whatever you’ve ordered.
176 Calle Duffaut
Chef José Enrique has become something of a darling in Puerto Rico’s culinary circles, particularly as he has achieved acclaim (most notably as a James Beard “Best Chef of the South” semifinalist) and lots of media coverage off the island. He’s been experimenting with many opportunities lately, including heading up hotel restaurants, but his cornerstone, the eponymous José Enrique, remains—and continues to be wildly popular among Puerto Ricans and visitors alike. The small restaurant, located inside a rehabilitated house rezoned as a commercial space, fills up quickly, so expect a wait for your chance to try one of the “contemporary Caribbean” dishes from a regularly changing menu. If you need entertainment while you’re waiting, head across the street to the Plaza del Mercado, where live music and dancing are often thumping on weekend nights.
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