The Best Things to See, Eat, and Do in San Juan

In a jewel-strewn Caribbean sea, what’s the case for coming to Puerto Rico, you ask? Excellent question. Come to this sunny, vibrant island to experience the surreal sensation of technically still being in the United States (same dollar, same president, no need for a passport) while also being in an entirely different country (gas by the liter, roads by the kilometer, Spanish by the earful). A trip here is a 3-for-1 bargain of Caribbean beaches, tropical rainforests, and splendid mountainscapes—with the rare added bonus of not one but three bioluminescent bays. There’s enough to see and do in Puerto Rico to keep you busy for weeks.

That said, at the top of any Puerto Rico itinerary should be San Juan, the thriving capital city where the majority of the island’s visitors disembark. Established in 1521, this is the oldest European-founded settlement in the US and the second-oldest in the Americas. You don’t have to squint too hard to see that rich history around you: The pastel-colored Spanish Colonial buildings and narrow cobblestone streets of the Old Town are protected by 17th-century fortresses and a 15-foot-thick zigzagging wall. Take a walking tour around Old San Juan to get the full effect. Also of historical import: The piña colada was invented here.

But San Juan is more than just charming old stuff and tourist shops. It’s a mosaic of ever-evolving neighborhoods, from the cosmopolitan Miami vibes of Condado to the hipster bars and street art of Santurce. Whether you’re here for the day or staying for an entire week, here are the best things to do in San Juan.

Puerto Rico’s tourism has rebounded to its pre-pandemic levels despite all the challenges. As a result, most of the hotels, attractions, and activities are available island-wide for your enjoyment.

At the time of writing, the only requirement for domestic travelers is to fill a declaration form at the dedicated Department of Health website. Non-US citizens (and long-term residents) are required to show proof of being fully vaccinated against COVID-19 before departure.

For international travelers, citizen or otherwise, the US entry requirements apply. Travelers must be vaccinated and have a negative COVID-19 test result taken no more than one day before departing for Puerto Rico.

Let’s do the touristy-but-can’t-miss stuff first, shall we? Two gigantic citadels front San Juan’s northern face. To the west, the 16th-century Castillo San Felipe del Morro (commonly known as El Morro) is undoubtedly one of the most well-known attractions in Puerto Rico. With its strategic location overlooking the San Juan Bay, El Morro defended this port city from 1539 to as recently as WWII.

Entry into El Morro costs just $10—save your ticket, because it also includes entry to “that other fort,” Castillo San Cristobal, within 24 hours of purchase. This is basically El Morro’s overlooked little sister, but San Cristobal is cool too! It’s the largest European fortification in the Americas and features the infamous Devil's Guerite (Garita del Diablo). Legend has it that soldiers would randomly disappear as they stood watch in this sentry box.

It's about a mile walk from one fort to the other, and the stroll alone is breathtaking, with pastel houses on one side and an arresting blue sea on the other. A mammoth esplanade fronting El Morro serves as a national gathering spot and is a great place to take a break.

After you visit the forts, stroll the waterfront down to La Fortaleza, another walled compound where the island's governor lives. You’re not allowed to go in—it’s literally the governor’s home and office—but you’ll see it well enough from the gate. In recent years, the first lady has taken the initiative to decorate Fortaleza Street leading up to the main gate. In the past, it’s been adorned with hundreds of colorful umbrellas, kites, butterflies, and a giant Puerto Rican flag floating above the street. Who knows what’s going to decorate the street when you visit!

Since 2012, the entry doors of a dilapidated building on San José Street have become an important symbol for Puerto Ricans living under the island’s current economic crisis. Artist Rosenda Álvarez originally painted the doors with the Puerto Rican flag, only to revisit her mural four years later, mute the red and blue colors of the flag, and paint them black instead. The change served as visual criticism of the controversial fiscal oversight board that is now controlling island finances. The building is now a popular photo spot among tourists and locals.

Even though it’s located right next to El Morro, this colonial-era cemetery is often overlooked by tourists. It lies just outside the wall, facing the sea. The Santa Maria Magdalena de Pazzis Cemetery is the final resting place of several prominent Puerto Ricans—among the most famous names found here are Pedro Albizu Campos, Jose Celso Barbosa, and José de Diego, among many others.

If you see a small kart with the word “piraguas” written on it, do not hesitate! Piraguas are crushed ice cones flavored with local fruit syrups like cherry, passionfruit, strawberry, tamarind, coconut, and lemon. Unfortunately they’re a dying tradition, but they can still be found in Old San Juan, especially near El Morro and Paseo la Princesa.

You’ll also notice homemade popsicles sold here and there at residents' front doors, usually for $1. These are paletas, flavored with just about every fruit on the island. Guava. Coconut. Other stuff. The orange-and-cream mix is somehow gooier than expected and also very refreshing—which was necessary around midday in the summer, when the city can be, ah, I'll just say it, oppressively hot.

The capitol building is a marble structure fronting the Atlantic, not far from Fort San Cristobal. Entrance is totally free Monday through Friday. Gaze upward at the ceiling, where the history of Puerto Rico is depicted in a stunningly detailed mosaic. Stand in the center of the rotunda, and you’ll be surrounded by glass-encased copies of the Puerto Rican and US constitutions. Outside, the Puerto Rican and US flags fly side by side.

First, check out the museum at Casa Blanca, a house built for the Spanish explorer Ponce de León and his family. De León, who famously (and futilely) searched for the fountain of youth, died on an expedition before he could move in.

Walk a few blocks to the San Juan Bautista cathedral, where Ponce de Leon did move in, and where he'll stay for eternity; he's entombed inside. There’s nothing fancy about the architecture, but San Juan Bautista is the oldest cathedral in Puerto Rico and the second-oldest in the Americas. In addition to the tomb of de León, it contains the shrine to Carlos Manuel Rodríguez Santiago, the first Puerto Rican and the first layperson in the history of the United States to be beatified.

About three blocks down from San Juan Bautista Cathedral, you’ll find this small chapel renowned for its healing powers. Built in 1753 at the edge of a stone cliff, this is the site where a miracle (allegedly) took place. The story goes that in 1753, a rider in the traditional horse race of the San Juan Bautista celebrations lost control of his horse, plunging to the cliffs below. The Spanish Secretary of Government, Don Mateo Pratts, watched the event unfold as he cried out, “Christ of Good Health, save him!” The horse didn’t survive the fall... but the rider did.

Ever since, thousands of faithful Puerto Ricans come on a weekly basis to pray for their own miracle. Note that the chapel is only open Saturdays and Sundays.

If you’re cool with pigeons and would like to recreate your favorite scene from Home Alone 2, wander into Parque de las Palomas (right next to Capilla del Cristo). As the name suggests, the park is plagued with hundreds of pigeons waiting for you to feed them corn or bird food, which you can buy from a local seller for a buck. They’ll stand on your head, arms, and shoulders as you feed them.

The park is temporarily closed, but the pigeons and sellers have organically moved to the street in front of the Capilla del Cristo to entertain visitors.

There are six shady plazas carved into the Old San Juan street grid. Walking around one afternoon, I came across Plaza Felisa Rincon de Gautier. It’s right outside the old Bautista Cathedral, named after the city's first female mayor. A busker who works the plaza every day was strumming an old ballad on his guitar. Two women, maybe in their 60s, very likely sisters, were singing along with him. They were belting it, really loud, getting really into it. The song brought out such emotion in them that I found myself choking up. When the song ended, the women cheered, hugged the guitar player, and went on their way. "That's very Puerto Rico," said a friend who lives on the island. "That's what we do."

Obviously, you can’t visit Puerto Rico and not go to the beach. Some of the island’s most stunning beaches are actually outside of San Juan. But there are several popular beaches worth a visit within the city.

Among these beaches is Isla Verde Beach, which was recently voted “Best Urban Beach” by USA Today. This is a popular choice by most locals and tourists who don’t want to venture too far from the city. Its sandy shore is three miles long and wide, so even on its most crowded days, there’s still space for you to relax. Isla Verde Beach is actually comprised of Pine Grove Beach, El Alambique, and Balneario de Carolina, with the latter having public bathroom facilities and its sand cleaned regularly.

Condado Beach is similar to Pine Grove Beach, but it tends to have a more touristy vibe than Pine Grove given the number of hotels in Condado. Still, this is an excellent beach to visit if you just want to dip in the water a step away from your hotel.

Ocean Park Beach is situated at the heart of Santurce, a popular district in San Juan. While the beach isn’t as big as the aforementioned ones, it still offers a relaxed atmosphere since it’s mostly surrounded by a park, homes, and local shops. You can walk to the now-bustling Calle Loiza to grab a bite at one of its many bistro bars, restaurants, and cafes.

Last but not least, if you want even more seclusion, head to Playa del Capitolio (Capitolio Beach) right in front of the Capitol Building. This small beach is rarely visited by tourists or locals due to its odd location. But if you’re looking for a narrow stretch where you can lay on the sand and relax away from the crowd, this is an excellent option.

La Perla has had a bad reputation for literal centuries. This historic shanty town was originally established in the 19th century to house former slaves and homeless servants who weren’t allowed to live within city walls. Today, the neighborhood enjoys newfound fame as the place where Luis Fonsi filmed his music video for “Despacito.” It was hit hard by Hurricane Maria and is still in the midst of rebuilding.

To check out the area, grab a drink at La Vergüenza, a popular bar right in front of the pedestrian entrance to La Perla. Once in, visit some of its chinchorros (small rustic bars) like La Cantina, La Perla Waterfront, and Palmas El Rincón de Paco to try real traditional Puerto Rican cuisine, local fritters, and its artisanal fusions.

Walk along the Malecón, where you can take beautiful photos of El Morro and get up close (the closest you can get!) to the ominous Garita del Diablo at the Castillo San Cristobal. Don’t forget to enjoy the street art painted all over the buildings along the Malecón and La Perla.

If you’re in the area on a Sunday night, go partying at La 39 Bar, a makeshift bar built on the roof of a house that was partially destroyed during the hurricane. Order a Medalla, the most popular beer in Puerto Rico.

Also featured in the “Despacito” music vid is the speakeasy La Factoria. This place is so famous among locals, it doesn’t even need a sign outside. It’s located where the popular Hijos de Borinquen bar used to be (you can still see the original name inside, painted on the wall), and La Factoria retains the low-key vibe of the iconic original.

It's tourist-friendly, but as you make your way inside, you'll find more than tourists drinking—and dancing—there. Beyond the hidden back door are four more individual spaces, including a wine bar, dance floor, and cellar-like bar, each with its own music, definitive vibe, drinks, and food. You might even get spendy and drop $9 on a cocktail.

Puerto Rico has no shortage of delicious street food, especially now that the food-truck craze has taken over the island. But Puerto Rico has had its own traditional food-truck dish for decades now—it’s called tripleta. What’s a tripleta? It’s a sandwich. Tripleta means three, so this sandwich has marinated grilled cube steak, ham or pork, and chicken. It’s served on a loaf of sweet potato bread with chips, mayonnaise, and ketchup. Trust me, it is delicious. Among the most popular tripletas is El Churry, found in Isla Verde and many other locales.

Beyond tripletas, Puerto Rico has a varied local cuisine that you shouldn’t miss trying. Head to Raices to taste their mofongo relleno (stuffed plantain with your choice of protein) served in a traditional pilón. La Cueva del Mar will serve you all things seafood with a very local vibe. And La Casita Blanca will indulge you with a mouthwatering home-cooked meal. This restaurant is literally set in a former home, and it’s decorated as if its former residents still live there.

Or, if you want to taste a bit of everything, you can’t go wrong with an authentic Puerto Rican food tour.

Ashford Avenue feels like a Caribbean version of Miami Beach, what with its Miami-style architecture, high-end stores, trendy hotels, and beachfront cafes. Walk along the avenue to soak in the atmosphere, chill at the beachfront Ventana del Mar Park, and have a vibrant night at the historic La Concha Resort.

Even though folklore takes the piña colada as far back as the 19th century, when Puerto Rican pirate Roberto Cofresí offered his crew a cocktail made with coconuts, pineapple, and rum to boost their morale, the “official” piña colada wasn’t invented until 1954 by Ramón "Monchito" Marrero at the Caribe Hilton. On the other hand, the famous restaurant Barrachina also claims that their bartender, Don Ramon Portas Mingot, invented the drink in 1963. While the hotel got the governor’s recognition in 2004 to commemorate its 50th anniversary, both locales still argue over who’s the real inventor of Puerto Rico’s national drink. So why not drink a bunch of both and decide which one is the most delicious?

If you’ve got money to burn, you must head to Plaza Las Americas—the largest shopping mall in the Caribbean and the second-largest in Latin America. With over 300 stores and “The Center of It All” as its slogan, this mall does indeed have it all, from high-end boutiques to local arts and crafts.

Located in the hip Santurce neighborhood, Lote 23 is basically a modernized version of the traditional beachside kiosks commonly found around the island. Here you’ll find young chefs using locally sourced products and experimenting with traditional Puerto Rican cooking techniques and new trends. Snack on criollo cuisine, burgers, “Asianrican” dishes, fish tacos, cocktails and craft beers, and more. It’s an open environment with picnic tables and live music—or if it’s a game night, a giant screen to watch sports.

Commonly known as La Placita, or the Little Market, this is the most popular hangout for locals during the weekend—especially Friday nights. Located in Santurce, La Placita is actually a colonial-style produce market during the day, but once it closes in the afternoon, the bars and restaurants surrounding it come to life until the early morning hours. You’ll find everything from reggaetón music clubs to salsa dance floors, gay bars, and even upscale restaurants, all in one place. The best part is how the crowd mixes on the street and hops between locales based on their mood.

You’ll see no shortage of impressive, ultra-vibrant murals all over San Juan, but if street art is your thing, head to Santurce. The annual contemporary art festival Santurce es Ley attracts some of the world’s most-talented street artists to decorate rundown buildings and empty parking lots around the neighborhood with stunning, large-scale murals. You’ll spot the majority of these colorful masterpieces on a walk down Calle Cerra and along its side streets. It’s often compared to Miami’s Wynwood District, and in fact features work from some of the same artists.

The biggest mistake you could make in Puerto Rico is not leaving San Juan. This fascinating island is small enough that you can get anywhere in just a few hours, and yet it’s absolutely packed with diverse landscapes, from mountains to rolling farmland and bioluminescent bays—heck, there's even a rainforest! El Yunque National Forest (yep, run by the familiar US Forest Service) is an easy day trip from the city; ride up in the morning, be back in the Old Town in time to watch the sunset over the harbor. Just $4 gets an adult into the park.

Another easy day trip from San Juan is a visit to one of Puerto Rico's sister islands, Culebra or Vieques. You can catch the ferry—which leaves from Ceiba—to either island. Culebra is more low-key, with fewer restaurants and services, but it does have Flamenco Beach, regularly ranked one of the best beaches in the Caribbean. Vieques also has beautiful beaches, likePlaya Caracas and Playa Negra, plus fun nightlife and waterfront restaurants. Stay overnightand go on a night kayaking trip at Mosquito Bay, the best and brightest bioluminescent bay in the world. The best time to go is in the darkness of a new moon.

Old San Juan is one of the most popular areas to stay in, especially if you want to stay in a Spanish Colonial building and be within walking distance to most attractions in the old city. There are dozens of accommodation options in the area, including the 4-star hotel El Convento—set in a former convent—Decanter Hotel, Casa Sol B&B, and of course, plenty of short-term rental apartments.

But definitely consider looking for accommodation outside of Old San Juan, especially if you’re renting a car, as parking in Old San Juan is quite limited. Condado is the go-to area for most tourists looking for a chain hotel or a more contemporary setting. The Caribe Hilton, Condado Plaza Hilton, Condado Vanderbilt, La Concha Renaissance San Juan Resort, and San Juan Marriott Resort are among the most-popular choices in the area. Further east and a step away from the airport is Isla Verde, where you’ll find the Fairmont El San Juan, Hampton Inn & Suites, Embassy Suites, and TRYP by Wyndham, among others.

For short-term rental apartments, in addition to the previously mentioned areas, you can also check neighborhoods like Santurce, Ocean Park, and Miramar for a mix of authentic early 20th-century homes and contemporary lofts. Pick your era, pick your pillow—it’s all in San Juan.

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