Puerto Rico is one of those rare destinations that manages to feel both electric and deeply grounded at the same time—and San Juan It is the beating heart of this island. It can be difficult to choose the best places to visit in the capital of the island. There are so many things to do. I am half Puerto Rican and have visited the island several times. cocktail barsBeautiful beachesThere are also dive bars and parties both indoors and outdoors that last late into the evening.
Every corner is a different temptation: a gallery filled with local art; a boutique that smells of tropical dreams and warm leather; a fort that whispers secrets about pirates and revolution. I’ve learned that when hungry, just follow your nose—it’ll lead you to sizzling mofongo, juicy lechón, and empanadas that demand a second round. At courtyard cafés, strangers can become fast friends over frosty Medalla beers and slow sunsets. The city is layered—historic but current, laid-back but alive. You just need to know how to fit it all in a 3-day itinerary.
For those who want to plan their trip, I have created a guide on how to spend three days at San Juan. It includes ideas for foodies, first-timers, and anyone else looking for the best of San Juan. adventurers Even the creatives who want to be inspired by art, culture and soul will find inspiration in this guide. This three-day itinerary includes recommendations for where to eat and stay, how to make the trip seamless, and top-rated guides who can take you on food walks or waterfall hikes.
In this article:
San Juan itinerary, day one
Get your bearings by going to Old Town on the first day. There, every step is a story. Music spills out like rum, and tumbling down into the cobblestone lanes that wind through the centuries-old architecture. The ocean is never far here—it clings to the edges of the neighborhood, and wraps its salty arms around candy-colored buildings.
Morning:
Start the day in Old San Juan. The pastel-washed building feel like a dream. The earlier you get out the door, the better—the city is best explored when it’s just waking up, especially in peak seasons, when the cruise ship crowds shuffle in around mid-day. Breakfast (or brunch) at Barrachina It’s almost a rite-of-passage. Whether or not it truly birthed the piña colada is irrelevant; its courtyard, flanked with tropical greenery and colonial arches, is soaked in laid-back local energy (and huge portions for all entrees).
If you want something more low-key and relaxed, consider a trip to Cuatro Sombras—a legendary café with rich aromas pouring out of it from the freshest of beans, grown in the shady mountain region of Yuaco.
From there, get delightfully lost wandering the streets of Old San Juan: Walk off breakfast by exploring the narrow corridors around Calle de San Sebastián, one of the most charming streets you’ll come across. (Come back here later for a lively strip of cafés and bars.) Make your way toward Callejón de la Puerta de la Bandera—the casual attraction is a vibrant-hued alleyway, with a backdrop of a large Puerto Rican flag. Wander along Calle Norzagaray, where you’ll find charming boutiques, colorful balconies and vintage streetlamps. A slew walking tours Base their routes on this street, as it is a long stretch that connects to two historic forts in the area. Don’t miss a peek at the regal and picturesque Palacio Provincial Hotel—a former governor’s mansion turned boutique stay.
Afternoon:
The iconic is the answer to culture’s call Castillo San Felipe del Morro. The island’s most iconic landmark, the Cuartel de Ballaja, is a place where you can find cannons with sweeping views of the Atlantic, like something from a classic pirate story. Cuartel de Ballajá is in front of del Morro—it was built from 1854 to 1864 in order to house the Spanish and Puerto Rican regiments in Old San Juan (and has since taken on many forms through history). If you crave art, stay close to the Humanidades inside Cuartel de Ballajá, a spacious, restored and newly-opened gallery marked by Moorish archways and an undulating ceiling that mimics the ocean just outside. The building acts as a center for the arts, also housing a dance school, music school and the Museo de Las Américas. Be sure to visit some of the galleries. Galerìa Botello This 350-year-old house has been converted into a gallery, which hosts contemporary local artworks. Nearby, of the many shops to splurge in, be sure to stop at the aesthetically-designed Gyspetter boutique, home to lots of fun accessories and trendy ‘fits.
A mid-day drink is available at El Batey. It is gritty, iconic and sticky with memories. The walls are covered with decades worth of stories and graffiti. During the day, the many arches that line the walls are fully open, pouring in natural light and a refreshing breeze—while also inviting local birds to stroll on in and hang amongst the buzzy local crowd.
Evening:
Before dinner, head to Ashford Avenue—the ritzy main street of Condado, is peppered with high-end shops, restaurants, and bars. Make it a priority to visit one of the many restaurants that you can choose from. La Concha Resort’s Shell-shaped Oceanfront Restaurant Space LevantIf you are staying at the property, or not, this is a great place to dine. This upscale dining space opened in San Juan, Puerto Rico, on March 20, 2025. The menu fuses Mediterranean flavors with fresh island ingredients. You can enjoy a variety of cocktails and dishes that are both creative and delicious. Māro is a fun-yet-elevated pick for Pacífico-Latina cuisine, home to entrees that feel like true artistry.
