The Top 12 Things to Do in San Juan, Puerto Rico

As the oldest city in the Western hemisphere, Viejo San Juan (also known as Old San Juan) was originally settled by the Spanish in the 16th century. Between the cobblestone streets and the pastel-hued, color-blocked architecture, this part of the city is an Instagram-lover’s dream. But don’t just visit for the selfies—Old San Juan is home to many historic sites, and the story of the city is best appreciated via a walking tour with a local guide. Even if you’re just passing through, it’s hard not to be impressed by the beauty of the city, particularly at Calle San Justo.

This UNESCO World Heritage Site in Old San Juan is the most popular historic attraction in Puerto Rico and is an absolute must-visit for guests visiting San Juan. The fort of Castillo San Felipe del Morro protected the capital from enemy ships and now provides views of the water and fascinating history for visitors. Construction originally began in 1539 by the Spanish, and in that entire time, it was only once conquered by land (and never by sea). It’s a tradition to fly a kite on the spacious lawn, so make sure to take up one of the local vendors on their offerings, and face into the wind.

A tree-lined street, Paseo la Princesa is also known as Walkway of the Princess. This idyllic promenade is picturesque during the daytime, but even more so at night. Sunset is the ideal time to visit, as there will be less tourists on the street, but still an enticing amount of local artisans selling souvenirs.

While visiting a cemetery may not usually be at the top of your list for must-do activities while on vacation, for this scenario, you must make an exception for the Old San Juan Cemetery, also known as the Santa Maria Magdalena de Pazzis Cemetery. With its majestic views of San Juan Bay, the cemetery is the burial spot for Puerto Rico’s most luminary citizens—from poets to politicians. Admire the tropical flowers and sculptures in this beautiful historic site, which was built in 1863.

There's more than one way to view the walled city of Puerto Rico, and though we've already suggested strolling along the Paseo La Princesa, San Juan is equally gorgeous when observed from the water. View the forts and the beautiful architecture from the sea, and get a sense of how intimidating the scale of the fortresses once were. We suggest sailing San Juan Bay at sunset for prime, pastel-colored vistas.

Check out the many outdoor galleries of Calle San Sebastian, but also keep your eyes peeled while strolling the cobblestone streets of Old San Juan. The curious traveler will discover an array of paintings and murals, depicting not only the loveliness of the island but also the political turmoil as well. Seeing the murals must-do for first-time travelers to the city, as well as for Puerto Rico's regular visitors. We also recommend the Galería Botello and the Obra Galería for a more traditional gallery experience.

You’d be remiss to visit Puerto Rico and not try the rum, as it is the island’s most popular beverage, and more than 70 percent of all rum purchased in the U.S. comes from Puerto Rico. In that spirit, make some time to have a tasting at the Bacardi Rum Factory, also known as the Casa Bacardi Puerto Rico. The largest of its kind in the world, to get a better appreciation for the local (alcoholic) flavor. The truly hearty should opt for a rum tasting tour.

Though Puerto Rico’s most famous beaches are located outside the capital city (and many of the best spots are on Vieques Island), there’s still plenty of opportunities for city visitors to relax on the sand. Visit Condado Beach, Ocean Park, or Pinegrove beach for the opportunity to lie in the sun. After all, the cobblestone streets on Old San Juan will still be there come sunset (and they'll be more alive than ever). 

There’s no shortage of artistic inspiration in San Juan, aside from the outdoor galleries of Calle San Sebastian, there is also a magnificent street art scene in Santurce. This neighborhood has been compared to Miami's Instagram-famous Wynwood, so get your selfie sticks ready, and prepare to hit the streets. Be sure to visit the Museo de Arte de Puerto Rico, also located in the artsy neighborhood.

Observe the beauty of San Juan Bay on one side and the formidable San Juan Gate on the other while walking the Paseo Del Morro. This walking trail was designated a National Historic Site in 2001 and is a wonderful way for visitors to acquaint themselves with the history and natural beauty of San Juan's walled city. This trail is a continuation of the Paseo de la Princesa, and you should begin your journey at San Juan Gate.

While you're in Puerto Rico, you must at least attempt to dance the salsa. Visit the speakeasy La Factoria to get the best dancing in town. The bar is consistently ranked as one of the best bars in the entire world, and the dancing only becomes more creative (and more invigorated) as the hours wane into the early morning.

You may recognize this town in Old San Juan as the setting for Justin Bieber's music video for "Despacito." La Perla (Spanish for "the pearl") has undergone a renaissance in recent years, as the vibrant city has become increasingly known for its colorful architecture and even more colorful nightlife. Located between the forts of San Cristobal and El Morro, this unique town is a must-visit for travelers looking to explore the local flavor and culture of Puerto Rico.