Go on a Guided Walking or Foodie Tour

If you’d prefer to learn more about the places you’re passing by on a stroll through the colorful streets of Old San Juan, consider booking a walking tour with guide Debbie Molina Ramos, who has been leading educational walks around the city since 1999. Choose from daytime or nighttime tours to see the area in a different light.

Those interested in tasting their way around the old city can choose from several foodie-themed tours by Flavors Food Tours and Spoon, which each offer small groups the chance to sample bites from different restaurants around Old San Juan and in some cases, rum-based cocktails, depending on which tour you choose.

Sip Piña Coladas Where They Were Created

While you can find piña colada cocktails all over Puerto Rico (it is the national drink, after all) it might be more memorable to indulge in the place they were created. Head to the Caribe Hilton, located on Calle San Gerónimo in Old San Juan, where, in 1954, bartender Ramón “Monchito” Marrero famously blended coconut cream, pineapple juice, and rum to create the world’s first piña colada.

Visit the Old Forts

History buffs, rejoice! Old San Juan is home to several massive fortresses whose cannons, ramparts, and layered defenses have guarded the walled city for centuries. Start by visiting El Morro (full name: Castillo San Felipe del Morro) and Castillo de San Cristóbal, which are among the most visited attractions on the island, and for good reason. Then, stop by the governor's mansion, called La Fortaleza (the Fortress) because it served as one of the Spanish settlement's early defensive structures.

Take a Sunset Stroll Along Paseo de la Princesa

Paseo de la Princesa ("Walk of the Princess") is a broad promenade that begins near the docks at the foot of the city and leads to the lovely Fuente Raíces (Raíces Fountain). On weekends, you're likely to find all kinds of stalls lining the road, and occasionally, a free musical or cultural performance to enjoy. Paseo de la Princesa hugs the old perimeter wall of the city and beyond the fountain, continues around Old San Juan to the San Juan Gate, the last remaining of the city’s original five entry points. The best time to enjoy the walk is during sunset when you can take in gorgeous views of the bay from the fountain and escape the midday heat.

Dance the Night Away

While salsa dancing and Puerto Rico go hand in hand, the island isn't exactly crawling with hallowed halls of salsa. While old standards like the Nuyorican Café (where Mick Jagger once danced the night away) have closed, newer spots like La Factoría and La Vergüenza Puertorrican Chinchorro—where you can also dance the rumba, bomba, and plena—in Old San Juan have really stepped up to the plate.

Check Out the Former Home of Juan Ponce de León

One of the oldest structures in Old San Juan, La Casa Blanca (also known as Museo Casa Blanca) was constructed in 1521 and served as the city’s earliest fortress as well as the home of its first Spanish ruling family. You might have heard of the man who made the search for the mythical Fountain of Youth his legacy, but before Juan Ponce de León took off on his chase for immortality, he built this home; his family and their descendants went on to live here for 200 years. The house provides a beautiful trip back through the ages and is definitely a historical highlight.

Discover the Old City's Nightlife and Dining Scenes

When it comes to the best lounges, bars, and nightclubs in greater San Juan, you'll find several of them in Old San Juan, a section of the island known for its active nightlife scene. Whether you prefer chic lounge vibes of upscale joints like Marmalade, grungy and funky bars like El Batey Bar, or multi-level discos (there are many to choose from), Old San Juan doesn't seem so old once the sun goes down.

Dining in Puerto Rico is also an incredibly rewarding experience, whether you're seeking local classics like mofongo, gourmet international cuisine, or a delightfully inventive fusion of Caribbean and global flavors. In Old San Juan, Calle de la Fortaleza (Fortaleza Street) has carved out its reputation as the city’s Restaurant Row, and is home to some of the best eateries in town; South Fortaleza, known as the SoFo District, even has its own biannual culinary festival. Of course, you don't need to restrict yourself to Fortaleza Street to enjoy good food in the old city, but the variety and quality of food options found here make it a good bet for a great meal.

Visit Legendary La Rogativa

Of all the lovely sculptures in Old San Juan, why single out La Rogativa (the procession)? Because of the story of Puerto Rican patriotism it tells. The monument, located in Plazuela La Rogativa near the San Juan Gate, commemorates one of the most evocative legends of the island. When the British attacked Old San Juan in 1797, a quick-thinking priest took it upon himself to lead the outnumbered soldiers and civilians on a religious procession through the city. Apparently the British mistook the citizens’ prayer march for reinforcements and abandoned their attack. The sculptures recreate the moment as a work of art for all time.

Shop for Handcrafted Souvenirs

There's nothing wrong with a T-shirt or a shot glass, but if you want something creative and original to remember your trip by, the island is known for its lovely arts and crafts and you can find plenty of souvenir options throughout Old San Juan. From iconic vejigante masks found in numerous shops to the hand-carved santos (wooden figurines), souvenir shopping in San Juan is a real treat.

Browse the Old City's Art Galleries

Old San Juan is a haven for artists and proudly houses numerous art galleries that are well worth a look. Leading the list is the outstanding Galería Botello, but it's not the only place to feature fine local and regional works. Obra Galería, which showcases modern and contemporary art, is also worth your time.