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The Best Things to Do in San Juan 2019

ViaHero · February 1, 2019

Wondering what to do in San Juan? Wonder no more—here’s the complete guide to the best things to do in San Juan, complete with all the history, food, art, nightlife, beaches, and festivals you have to experience. After you’ve added these gems to your Puerto Rico itinerary, feel free to send us a message with any questions you still have!

Want to explore Puerto Rico differently? Have a local plan your trip.

Experience the unparalleled history

Discovering the history is one of the things to do in San Juan

Founded in 1521, San Juan is the third-oldest city in the Caribbean. Even if you’re not a history buff, Old San Juan’s stunning 500-year old forts, monuments, and cathedrals absolutely cannot be missed. If you’re traveling to San Juan, these sites are all must-visits (trust us on this one):

  • Castillo San Felipe del Morro: A 16th-century Spanish fort that’s one of Puerto Rico’s most iconic tourist attractions (we guarantee you’ve seen tons of pictures of it). And yes—it’s well worth a visit.
  • La Fortaleza: The 500-year old mansion where Puerto Rico’s governor resides. It’s beautiful.
  • Castillo San Cristobal: The lesser-known sister fort of del Morro, San Cristobal is actually (we think) a much more enjoyable experience. Fewer tourists, more freedom to roam, spooky tunnels under the fort, and gorgeous views above.
  • Paseo de la Princesa: The colonial plaza that winds beneath San Juan’s old city wall. The path circles the city wall on one side and borders San Juan harbor on the other. There are antique lights, palm trees, cafes, outdoor markets, and of course, amazing views.
  • Raíces Fountain: This gorgeous fountain is located on Paseo de la Princesa and is one of Puerto Rico’s must-sees. Head over at sunset for an amazing view.
  • Callejon de la Capilla: This quaint avenue is known for San Juan’s famous blue cobblestones (read more about them in this San Juan travel guide).
  • Plaza de la Rogativa: Often thought of as the most beautiful plaza in San Juan. Get some advice from a local for the best places to roam in and around the plaza.
  • Puerta de San Juan: The last of the major colonial gates through the old city wall, where dignitaries of the Spanish Crown were received for hundreds of years.
  • San Juan Bautista Cathedral: San Juan’s 16th-century cathedral. While it may look simple, it’s the burial place of conquistador Ponce de Leon!

Pro tip: A couple of these sites were damaged in Hurricane Maria back in 2017, but as of 2019 they’re all back to normal. Check out this article on traveling to Puerto Rico right now for more info.

Eat the delicious food

Eating is one of the things to do in San Juan

Foodies, unite! With everything from gourmet restaurants to creative food carts, San Juan is a true foodie destination (just one of the many reasons to travel to Puerto Rico) Here are some of the places you have to eat:

  • Casa Cortés Chocobar: A restaurant with a chocolate-centered menu that’s bound to be one of your trip highlights (and with chocolate sandwiches and lava cake, who could blame you).
  • Jose Enrique: A rising star of a restaurant that takes Afro-Caribbean cuisine to a whole new level. Reservations here are a hot commodity, so have an in-country local call ahead for you in advance.
  • The Miramar Food Truck Park: A local favorite in Santurce for Puerto Rican-Asian-Mexican fusion cuisine (yes, that’s a thing).
  • Acapulco Taqueria Mexicana: For travelers wanting a taste of something new, this traditional Mexican restaurant is part of Calle Loiza’s thriving culinary scene.
  • Juan Jose Cuevas 1919: A five-star restaurant in the glitzy Condado Vanderbilt Hotel. It’s delicious, unsurprisingly.
  • Perla: A breath-taking contemporary restaurant known for its awesome seafood menu.
  • Double Cake: A bakery on Calle Loiza known for low prices and “Coquito Mini Loafs,” sweet frosted bread named after Puerto Rico’s coqui frogs.
  • El Jibarito: A perennial classic, El Jibarito is known for its delicious and affordable Puerto Rican staples.

Pro tip: Puerto Rico is especially known for its fried street food—think empanadas and bacalaitos. You can find them all over the place, but we’d recommend asking a local for their favorite spots.

Check out the amazing art

Checking out art is one of the things to do in San Juan

From whimsical graffiti to classical museums, San Juan’s art scene is absolutely unreal. If you’re an art lover, these hotspots are total must-sees:

  • Espacio 1414: A contemporary gallery of Puerto Rican art in the heart of Santurce (San Juan’s hipster neighborhood), 1414 is awesome for anyone who loves modern art. Entry is by appointment only, though, so make sure to chat with a local about how to make reservations.
  • Calle Cerra: Santurce’s go-to spot for fantastic graffiti and street art, Calle Cerra is covered in amazing murals.
  • Mundo Taino: A local artisan shop for cookery and gifts in Old San Juan with easily some of the best gifts to bring home from Puerto Rico.
  • Galería Botello: A modern art gallery nestled on quaint Calle del Cristo, super close to some of San Juan’s famously awesome places to stay.
  • Museo de Arte de Puerto Rico: A perfect medley of history and art, this museum features everything from indigenous Taino art to contemporary works.
  • El Mercado Libre: A local market in Santurce with super fresh produce and locally-crafted art, this is also a fantastic place to support local artisans.
  • El Cuadrado Gris: A video and contemporary art gallery, El Cuadrado Gris is an off-the-beaten-path Puerto Rico attraction you have to check out.

Pro tip: Whether you want to take an art tour through PR or just see the island like a local, there are a ton of unique ways you can travel to Puerto Rico in 2019. Check out more info here.

Chill on the world-renowned beaches

Chilling on the beach is one of the things to do in San Juan

San Juan is by no means a concrete jungle; the city is right on the Caribbean, so visitors have access to amazing beaches right in the city itself. Here are some favorite areas:

Experience the unreal nightlife

Partying is one of the things to do in San Juan

San Juan is a nightlife hub—so even if you’re not a bar-and-club type person, you’re going to want to experience it for yourself. Oh, and in Puerto Rico nightlife isn’t just for the kids—people of all ages are out every night, living it up. Don’t believe us? Ask a local. Here are some places you have to see:

  • La Placita de Santurce: The central plaza of Santurce, La Placita full of outdoor bars and restaurants. The minute the sun goes down, it’s packed with locals of all ages eating, drinking, and dancing the night away. This is where you’ll find most of the best nightlife spots in the neighborhood.
  • Bar La Factoria: A world-famous hipster bar in the heart of Old San Juan, La Factoria is known for its local twists on classic cocktails.
  • La Respuesta: A popping bar with stand-up comedy and mouth-watering cocktails, La Respuesta is perfect for those doing Puerto Rico on the cheap.
  • Club Brava: An upscale club in Isla Verde where salsa dancing is the name of the game.
  • El Boricua: A laidback bar known for live music, El Boricua is down in Rio Piedras—San Juan’s college neighborhood.
  • Piso Viejo 1917: A tapas bar with hipster vibes (starting to see a theme here?) and off-the-wall salsa nights.  
  • Eternal Lobby Lounge: A futuristic cocktail bar on a world-famous seaside street in Condado.
  • El Batey: One of the oldest bars in Old San Juan, El Batey has spectacular live bands.

Pro tip: There’s amazing nightlife in San Juan no matter what you’re into, so make sure to get some tips from a local before you plan your night out.

Turn up at San Juan’s world-famous festivals

Going to a festival is one of the things to do in San Juan

With a major festival, sports event, or holiday at least once a month, San Juan is Puerto Rico’s #1 place to celebrate—which also ensures that you’ll never want for things to do. Here are just a few of the awesome festivals you can experience:

  • Three Kings’ Day (Jan. 6): Part of the Catholic celebration of Epiphany, complete with gifts and traditional songs—basically Puerto Rico’s extended Christmas.
  • San Sebastián Street Festival (Jan. 16-20): Puerto Rico’s version of Mardi Gras, with parades, drinking, and dancing. It’s one of the best things you can experience in Puerto Rico’s off-peak season, which is, ironically, actually the best time to visit Puerto Rico.
  • Casals Festival (March 6-13): A classical music showcase with world-famous composers and orchestras.
  • Saborea (April 4-7): A food festival for the ages where famous chefs, breweries, and wineries share their award-winning delicacies.
  • Puerto Rican Danza Week (May 13-18): Five days of traditional dancing that can get a little crazy (believe us, this isn’t your grandma’s dance party).
  • San Juan Bautista Day (June 24): A strange but awesome celebration of Saint John the Baptist’s birthday in which people walk backward into the ocean (seriously, it’s a trip).
  • Heineken Jazz Festival (July 15-19): An annual festival drawing curious travelers, beer lovers, and jazz fanatics from around the world.

Pro tip: If you want to experience any or all of these amazing events, just ask a local for help planning your trip.

While we hope you enjoyed these examples, the full list of amazing things to do in San Juan is pretty much limitless. Don’t miss any highlights—have one of our Puerto Rican locals (AKA Heroes) help plan your trip. Any questions? Just send us a message! And for more tips on San Juan and beyond, check out: