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Visiting San Juan for the First Time? Here’s What to See and Do

From the food to nature and everything in between, here's how to make the most of your first trip to San Juan.
Hi, I'm Jessica!

Jessica is a widely-published travel and food content creator. She’s the founder of The Dining Traveler, and the author of the coffee table book, The Dining Traveler Guide to Puerto Rico. Her writing and photography have been featured in publications such as AFAR, Business Insider, Travel and Leisure, among others. She was raised in Puerto Rico and began traveling as a young Marine 25 years ago. From serving as a translator in the Senegalese countryside to interviewing chefs in Peru, she loves learning about cultures, food, and people. She has traveled to over 60 countries and lived in six. Follow her on Instagram, Facebook, Twitter, Pinterest, and YouTube @DiningTraveler.

San Juan, the capital of the Caribbean hot spot Puerto Rico, boasts over 500 years of history and extensive cultural and natural wonders, including cascading waterfalls, pristine islands, delicious cuisine, and a sizzling music and dance scene. Whether you’re going for a weekend getaway or staying on an extended vacation, there’s plenty to see and do, especially if it’s your first time in Puerto Rico. Don’t miss these exciting activities, from chowing down on local food to dancing in public squares and spotting marine life in the island’s clear waters.

1. Learn about Puerto Rico’s history in Old San Juan

castillo san cristobal, san juan, puerto rico
The 18th-century Castillo San Cristobal is a military marvel.Photo Credit: Terri Butler Photography / Shutterstock

One of the oldest spots in North America.

Old San Juan is one of the oldest cities in the Americas, dating back to 1521 when the Spanish colonized Puerto Rico and established a settlement and the fort, Castillo San Cristobal. Today, Old San Juan is a vibrant town, lined with colorful historic buildings with fantastic restaurants, bars, and shops. Explore the cobbled streets on your own or via a walking foodie tour to learn more about this charming town’s long history and sample local cuisine.

2. Eat and dance at La Placita de Santurce

corner bar, la placita de santurce, san juan, puerto rico
La Placita de Santurce is a true day-to-night spot.Photo Credit: sanju_222323 / Tripadvisor

Food and music are the heart of Puerto Rican culture.

If visiting San Juan for the first time, add an evening at La Placita de Santurce (Santurce Market) to your list. During the day, fruit and vegetable stands line the market, and small cafés offer hearty Puerto Rican lunches (try mofongo, a filling dish made from mashed plantains). At night, the area comes alive with locals and tourists dancing salsa and reggaeton and trendy restaurants offering meals at every price range.

Related: Around Puerto Rico in 16 Dishes

3. View Old San Juan from the sea

old san juan, puerto rico, viewed from the sea
The ocean is a natural part of island life.Photo Credit: Darryl Brooks / Shutterstock

View the island from its clear waters.

If you’re traveling to San Juan on a short trip, the best and most beautiful way to see it (while maximizing your time) is by boat. Take a sunset sailboat tour to soak in the beauty of the Old San Juan coastline from the sea. Plus, see historic landmarks such as Castillo San Cristobal and Condado, San Juan’s most popular beach resort area, from a different vantage point.

4. Indulge in Puerto Rican street food in Piñones

fried street food in piñones, san juan, puerto rico
The street food in San Juan and the surrounds shouldn't be skipped.Photo Credit: C2428SBbenjaminl / Tripadvisor

Taste San Juan’s foodie delights with an ocean view.

Do what many locals do with their time off: Head to Piñones, a beach area about 15 minutes away from San Juan. The neighborhood’s streets are lined with kiosks offering decadent fried Puerto Rican street food like pastelillos (empanadas) filled with stewed crab, savory minced meat, or just cheese or a crispy bacalaíto, a fritter with chunks of codfish. Sip on a cold, refreshing coconut while listening to music, dancing, and enjoying the lively atmosphere.

Related: Don’t Miss Dishes in San Juan

5. Go paddleboarding along the Condado Lagoon

kayakers at sunset, san juan, puerto rico
Kayaking is a good alternative to paddleboarding for those with not-so-great balance.Photo Credit: Dennis van de Water / Shutterstock

Say hello to the manatees.

Condado, the lively sandy beach area of San Juan, is home to the Condado Lagoon, which houses a sizable population of manatees. The calm waters of the lagoon also make it the perfect place to go paddleboarding, while admiring the contrast between nature and the modern buildings surrounding the lagoon. Try paddleboarding or a glass-bottom kayak tour in the morning, or a night kayak tour to enjoy the tranquility of the mangroves once the sun sets.

6. Learn about the history of Bomba music and dance in Loíza

woman and child in front of ocean, puerto rico
Loíza is known as a cultural hub, but it also has lovely beaches.Photo Credit: Dora Ramirez / Shutterstock

Dive deep into Puerto Rican culture.

Discover Puerto Rico's rich African heritage in Loíza, home of the beloved cultural dance Bomba. Many bars and restaurants feature the exhilarating rhythms Bomba music and dance, so you can watch or join in with the locals.

Before or afterwards, get a feel for the area by touring the Parque Histórico Cueva Maria De La Cruz, home to a massive cave; dive into the vibrant world of artist Samuel Lind at his art studio, where he created colorful works featuring dancing and joy; and embrace the traditions of Loiceño folklore by admiring the Vejigante masks, special face coverings found at artisan shops and studios around the town. And, of course, you can always visit the area's beaches for some surf and sun.

7. Head to the mountains for traditional Puerto Rican food

roast pig on a spit, puerto rico
Lechón asado is one of the best Puerto Rican dishes.Photo Credit: Christa E / Tripadvisor

Get your Puerto Rican culinary education at a higher altitude.

Savor the flavors of Puerto Rico in the neighborhood of Guavate, renowned for its Ruta del Lechón, where restaurants serve the exquisite Puerto Rican lechón (roasted pork). Cafeteria-style restaurants, lechoneras, line the streets, each offering a unique take on this delectable delicacy. And after satisfying your taste buds, head to Charco Azul, nestled in the heart of the Carite Forest, and take a dip in the swimming hole surrounded by lush tropical vegetation.

8. Go on a rum-tasting tour in the rum capital of the world

casa bacardi sign, san juan, puerto rico
Casa Bacardí offers tours and tastings.Photo Credit: Bacardí Distillery Tour / Tripadvisor

Indulge in the sweet, strong booze.

Puerto Rico is known as the rum capital of the world. If you’re looking for a fun and educational experience, check out Casa Bacardí in Cataño, which hosts various events such as general tours and mixology classes. For those looking for craft rum experience, head to the town of Bayamón, home of Ron del Barrilito—one of the oldest rum producers on the island—and a massive waterfall that's also well-worth visiting.

9. View street and museum art in Santurce

museo de arte de puerto rico, santurce, puerto rico
El Museo de Arte de Puerto Rico is housed in a neoclassical building.Photo Credit: BMSunny / Tripadvisor

Puerto Rico is more than beaches and music.

Discover the essence of Puerto Rican art at the Museum of Art of Puerto Rico (El Museo de Arte de Puerto Rico), housed in a magnificent neoclassical building. The museum boasts a rich collection ranging from 17th-century religious artworks to contemporary masterpieces, encompassing a diverse array of sculptures, carvings, and posters.

After visiting the museum, walk around the Santurce neighborhood, especially Calle Cerra, to see stunning murals created by local artists depicting contemporary scenes of Puerto Rican culture.

10. Take a day trip to the East Coast (and its islands)

white-sand beach with catamarans, puerto rico
Take a water taxi out to Cayo Icacos.Photo Credit: SVongpra / Shutterstock

Swim with turtles along the pristine beaches.

Condado, the lively sandy beach area of San Juan, is home to the Condado Lagoon, which houses a sizable population of manatees. The calm waters of the lagoon make for the perfect place to go paddleboarding and see the contrast between nature and the modern buildings surrounding the lagoon. Try paddleboarding or a glass-bottom kayak tour in the morning, or a night kayak tour to enjoy the tranquility of the mangroves once the sun sets. And don't miss a visit to Cayo Icacos, an uninhabited island with a beautiful beach.

More things to do in San Juan

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