Top 10 Things to Do in Old San Juan

Street paved with Blue Cobblestone in Old San Juan, Puerto Rico
••• Zen Rial / Getty Images

Old San Juan is one of the best places in all of Puerto Rico. It has no beaches, no resort hotels, and not a whole lot of natural beauty. What it does have is over 500 years of history, beautiful colonial architecture liberally splashed with tropical colors and a timeless magic that makes it one of the most enchanting destinations in the Caribbean. You could spend many happy hours just walking around the walled city. But if you want to experience the best of Old San Juan, here are its top 10 experiences.

  • 01 of 10

    Visit the Forts

    El Morro Fortress in Old San Juan
    ••• El Morro Fortress. Walter Bibikow/The Images Bank/Getty Images

    Perhaps nothing captures the history of Puerto Rico more than Old San Juan's massive fortresses. El Morro and ​Castillo de San Cristobal are among the most visited attractions on the island for good reason. Their cannons, ramparts, and layered defenses have guarded the walled city for centuries. Even the governor's mansion, La Fortaleza, is called "The Fortress" because it was one of the settlement's early defensive structures.

  • 02 of 10

    Dine Out on Fortaleza Street

    Dining in Puerto Rico is usually a rewarding experience, whether you're after local Rican classics, gourmet international cuisine, or a delightfully inventive fusion of Caribbean and global flavors. In Old San Juan, Fortaleza Street has carved out a reputation as a Restaurant Row that includes some of the best restaurants in town. In fact, South Fortaleza, or "SoFo," as it's known, even has its own biannual culinary festival.

    Among the restaurants that you'll find here are:

    • The Parrot Club
    • Dragonfly
    • Aguaviva

    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 found here make it a good bet for a great meal.

  • 03 of 10

    Take a Sunset Stroll Along Paseo la Princesa

    Paseo De La Princesa Fountain
    ••• The Raíces Fountain. George Oze Photography / Getty Images

    Paseo La Princesa is a broad promenade that stretches from near the docks at the foot of the city and leads to the lovely Raíces Fountain. On weekends, you're likely to find all kinds of stalls lining the road, and maybe even a free cultural performance to enjoy. Paseo 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 only remaining of five entry points into the old city.

    The best time to enjoy the walk is during sunset when you'll have gorgeous views of the bay from the fountain and you'll escape the heat of the day.

  • 04 of 10

    Go Salsa Dancing

    Salsa and Puerto Rico go hand in hand, but surprisingly, the island isn't exactly crawling with hallowed halls of Salsa. Fortunately, my favorite destination for fantastic live Salsa music can be found in Old San Juan, my favorite destination for fantastic live Salsa music can be found in Old San Juan at the Nuyorican Café.

    Continue to 5 of 10 below.
  • 05 of 10

    Check Out the Home of Ponce de León

    One of the earliest structures in the old city, La Casa Blanca was both its earliest fortress and home to its earliest ruling family. You might have heard of the man who made his legacy the search for the mythical Fountain of Youth. Well, before he took off on his chase for immortality, he built this home, and his family lived here for 200 years. Today, the home is a wonderful trip back through the ages, and one of the cultural highlights of Old San Juan.

  • 06 of 10

    Enjoy the City at Night

    Take a look at the best lounges, bars, and clubs in San Juan. You'll find several of them in Old San Juan, a city known for its active nightlife. Whether you prefer the chic lounge scene (try Dragonfly or Marmalade), grungy and funky bars (El Batey leads that pack) or multi-level discos (Club Lazer), Old San Juan doesn't feel so old once the sun goes down.

  • 07 of 10

    Visit La Rogativa

    Of all the lovely sculptures in Old San Juan, why do we single out La Rogativa? I think it's because of the story it tells. The monument, located in a quiet corner of the city near the San Juan Gate, commemorates one of the most evocative legends of Puerto Rico.

    In 1797, the British attacked Old San Juan; outnumbered and facing defeat, a priest led a religious procession through the city. The British, mistaking the citizens for reinforcements, abandoned the attack.

  • 08 of 10

    Book a Nighttime Walking Tour of the City

    Old San Juan is beautiful by day, but truly magical at night. And there are two tours that show you the city at night in a special way.

    • Debbie Molina's Night Tales is a wonderful walking tour of the old city. Debbie takes you inside buildings you don't normally get to see at night and regales you with fascinating stories from the city's past.
    • Leslie Padró's Flavors of San Juan combines historical anecdotes with a chance to savor dishes at several local restaurants.
    Continue to 9 of 10 below.
  • 09 of 10
    Traditional vejigante masks
    ••• Traditional vejigante masks. Walter Bibikow / Getty Images

    Puerto Rico has amazing hand-crafted souvenirs. There's nothing wrong with a t-shirt or a shot glass, but if you want something original, this island has wonderful arts and crafts, and you can find plenty of options in Old San Juan. From the iconic vejigante masks found at numerous shops to the hand-carved santos to the Panama hats at Olé, souvenir shopping in San Juan is a treat.

  • 10 of 10

    The old city is a haven for artists, and it 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 showcase fine local and regional works.