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Things to do in Old San Juan range from uncovering centuries-old forts to feeling the vibrant local culture. This vibrant, historic neighbourhood in Puerto Rico blends Spanish colonial origins with Caribbean sass. Walk on cobblestone streets, visit sites such as El Morro, admire street art, or take an easy break at a lively plaza. Go to museums, sip on piña coladas, or see the sunset along Paseo de la Princesa. From ocean vistas to cultural events, activities in Old San Juan provide the best mix of history, charm, and unforgettable island experiences for all types of travellers.
Top 10 Things To Do In Old San Juan
Explore historic forts, vibrant plazas, neighbourhood murals, and Puerto Rican cuisine while trying these amazing things to do in Old San Juan.
1. Walk The Historic Ramparts Of El Morro Fort
Photo: P. Hughes / Wikimedia Commons
Visit Castillo San Felipe del Morro, or simply El Morro, a recognisable landmark, one of the top things to do here. Perched above San Juan Bay, this 16th-century Spanish fort was built to protect the island from seaborne attack. Today, it’s a touching reminder of Puerto Rico’s colonial past. Walking its serenity-chiselled stone walkways and standing on cannon-embrasured ramparts, you will cherish the history that shaped the Caribbean. If you are intrigued by history or just a passing visitor, a tour of El Morro is one of the most unforgettable Old San Juan experiences.
Major Highlights: Sea views, colonial architecture, historic tunnels
Location: 501 Calle Norzagaray, San Juan, 00901, Puerto Rico
2. Explore Tunnels And Towers At San Cristóbal Castle
Photo: LBM1948 / Wikimedia Commons
Castillo San Cristóbal is the largest Spanish fort in the New World and an absolute must-see in Old San Juan. Stretching across 27 acres of ground, this gargantuan fortress was constructed to protect the city from land-based invasions and features a complex system of tiered defences, tunnels, and dungeons that will stir your imagination. As you make your way through its maze-like passages and climb up onto the top viewing platforms, you’ll be treated to bird’s-eye vistas of the Atlantic Ocean and San Juan’s lively streets. Walk along sentry paths and picture the existence of Spanish soldiers who once stood guard here.
Major Highlights: Panoramic views, secret tunnels, history exhibits
Location: 501 Calle Norzagaray, San Juan, 00901, Puerto Rico
3. Take A Stroll Along The Paseo De La Princesa Promenade
Photo: Edgar Torres / Wikimedia Commons
Paseo de la Princesa is the most romantic and culturally engaging encounter in Old San Juan. This 19th-century promenade, just outside the walled city, is a culturally historic and community-rich romanticism. Begin your walk at the renowned Raíces Fountain, a beautiful sculpture symbolising Puerto Rico’s multicultural heritage of African, Spanish, and Taino origins. Subsequently, stroll along a tree-canopied walkway lined with colonial buildings, street vendors, and quirky local art. Musicians will likely play their traditional instruments, providing rhythm for your walk. The aroma of Puerto Rican street food like empanadillas and piraguas fills the air.
Major Highlights: Street food, art stalls, musical evenings
Location: FV7M+9CV, Paseo de la Princesa, San Juan, 00901, Puerto Rico
4. Pay A Visit To San Juan Bautista Cathedral
Photo: Diego Delso / Wikimedia Commons / Image For Representation Only
One of the best things to do to reward yourself in Old San Juan is a trip to San Juan Bautista Cathedral. It’s one of the oldest cathedrals in the Americas, full of centuries of history, religion, and architectural wizardry. Built in a stunning Gothic style, the cathedral is not only a place of worship but also a historical landmark, serving as the final resting place of Spanish explorer Juan Ponce de León. Step inside and you’ll be greeted by soft light filtering through intricate stained-glass windows, stone archways, and statues that echo the devotion of generations.
Major Highlights: Ponce de León’s tomb, traditional architecture, stained glass
Location: 151 Calle del Cristo, San Juan, 00901, Puerto Rico
5. Take Photos Under Umbrellas On Calle Fortaleza
Photo: Ligocsicnarf89 / Wikimedia Commons
The La Fortaleza and Calle Fortaleza tour is one of the most renowned things to do here. La Fortaleza, or “The Pink Palace,” is the Puerto Rican governor’s official residence and UNESCO World Heritage Site. Calle Fortaleza, the quaint palace street, is famous for its ever-changing overhead art installations, from dripping umbrellas to whimsical kites and lanterns. The block has become Puerto Rico’s most photogenic spot, merging colonial structures with vibrant modern imagination. Browse boutique shops, cosy cafes, and vibrant art galleries as street performers and vendors spice up the air.
Major Highlights: Vibrant canopy displays, palace views of the government, boutique shopping
Location: San Juan, 00901, Puerto Rico
6. View Afro-Caribbean Art At Museo De Las Américas
Photo: Daderot / Wikimedia Commons
A visit to Museo de Las Américas is one of the most significant things to do in Old San Juan. Located in beautifully restored Spanish military barracks of the Cuartel de Ballajá, the museum offers detailed insights into Puerto Rican and Caribbean local identity. Taíno native heritage, African ancestry, and vibrant people art are some of its permanent exhibits, completing a whole cultural experience for history enthusiasts and passing voyeurs alike. The building itself is also part of the intrigue, with open courtyards, arched walkways, and colonial beauty. In addition to the permanent exhibit, the museum also sometimes includes rotating art exhibits, movie screenings, and cultural classes.
Major Highlights: Afro-Caribbean exhibits, folk art, contemporary works
Location: Cuartel de Ballajá, Segundo Piso, Viejo San Juan, San Juan, PR, 00926
7. Enter Old San Juan Through The Iconic San Juan Gate
Photo: Kris Arnold / Wikimedia Commons / Image For Representation Only
Walking through the San Juan Gate (Puerta de San Juan) is one of the most iconic things to do here. This handsome red gate, once the official welcoming gate for visiting dignitaries arriving by sea, is now a symbolic and historic entrance into the walled city centre. Approaching along scenic Paseo del Morro, you’re greeted by stunning views, crashing Atlantic surf, ancient walls, and greenery clinging to the shoreline. Even the gate itself, massive and imposing, is a story in quiet of San Juan’s former power and splendour. Visit during golden hour when sunbeams soak the stone in golden hues, perfect for a photo shoot or a serene beach walk.
Major Highlights: Coastal views, historic entrance, ocean walk
Location: FV8J+354 Caleta de San Juan, San Juan, 00901, Puerto Rico
8. Shop Artisan Goods On Calle Del Cristo
Photo: P. Hughes / Wikimedia Commons
Strolling along Calle del Cristo and seeing the Chapel of Christ the Saviour (Capilla del Cristo) is among the most fascinating activities in Old San Juan. The ancient cobblestone street, steeped in romance, leads you to a small cliff-top chapel that’s full of legend. It is said a horse and rider narrowly escaped death when they plunged off the edge of the cliff during a race, prompting the chapel’s construction in the 1700s. Inside, there are silver offerings and devotional art that maintain its otherworldly, spiritual ambience.
Major Highlights: Boutique shopping, local legends, ocean views
Location: San Juan, 00901, Puerto Rico
9. Sip Cocktails And Dance Salsa At La Factoría
Photo: Valeria Boltneva / Pexels / Image For Representation Only
At dusk, the entire other side of the city turns alive, and experiencing it is one of the best things to do. The nightlife at night here pulses with credibility, culture, and rhythm. Begin your night at La Factoría, an unlisted bar that appears annually on the world’s best bars lists. In its labyrinth of rooms, you can enjoy expertly concocted cocktails, soft lighting, and impromptu salsa dancing. In walking distance is Nuyorican Café, infused with a different kind of vibe, live jazz, poetry slams, and spoken word performances celebrating Puerto Rico’s vibrant cultural heritage.
Major Highlights: Craft cocktails, live music, dancing
Location: 51 C. de San José, San Juan, 00901, Puerto Rico
10. Enjoy Bay Views On The Ferry Ride To Cataño
Photo: Moebiusuibeom-en / Wikimedia Commons / Image For Representation Only
Maybe the most underutilised activity in Old San Juan is to ride the local ferry between Cataño, a brief but breathtaking ride across the bay. Like Sydney’s Manly ferry ride, the trip is a wind-whipped escape from the insanity of the city and opens another face of Puerto Rico. As the ferry sails over the water, riders receive all sorts of postcard-perfect scenery: the pastel-colored skyline of Old San Juan, the imposing mass of El Morro, and the sparkling Caribbean stretching out to the horizon.
Major Highlights: Scenic drive over the bay, Bacardí Distillery stop, glimpse of local life
Location: FV7P+9PG, Calle Marina, San Juan, 00901, Puerto Rico
Old San Juan is a timeless treasure where beach beauty, culture, and history meet. Cobblestone streets lined by pastel-colored buildings, old forts, and vibrant plazas, there are numerous things to do in Old San Juan. Whether you are a history enthusiast or a hedonist, the city provides a unique combination of activities which linger long after you have departed. Therefore, let TripXL organise everything for you as you wish.
Cover Photo: Brad Clinesmith / Wikimedia Commons
