Colonized by the Spanish in 1530, Old San Juan, known to the locals as Viejo San Juan, is the oldest city in the U.S. and its territories. This historic city is walled-in and teeming with colorful colonial architecture, forts and an eclectic culture ready for your to explore. Experience the many things to do in Old San Juan like a local would with our off-the-beaten-path guide.

Old San Juan, Puerto Rico

Grab a Bite on Fortaleza Street

Sightseeing isn’t wise on an empty stomach, so first on our list is a walk down the city’s cobblestone streets for a bite to eat at any of the local Old San Juan restaurants on Fortaleza Street. Here you can try Puerto Rican specialties like Mofongo, a savory dish of deep-fried plantains seasoned with spices and paired with shrimp, pork or veggies. Be sure to order a delicious Frappe de Mango too, a sweet mango smoothie filled to the brim that’s delicious for breakfast, lunch, or just an afternoon snack. Puerto Rican cuisine is a mix of European, African and native Taíno culture, a delightful fusion of flavors that will entice your palate regardless what you choose. Some of the best restaurants in San Juan Puerto Rico where you can find authentic local flavors are The Parrot Club, El Jibarito, and Marmalade.

Explore Iconic Sites 

Travel through time at Ponce de León’s “Casa Blanca,” otherwise known as the White House, in Old San Juan. The home was built in 1521 by one of the world’s most famous explorers, Ponce de León. Now a museum, the landmark is a cultural treasure that’s a must-see on your agenda. Take a guided tour and travel through the 1500’s to the 1800’s inside the rooms decorated with authentic furniture and photographs of the times.

When you’re done, marvel at the architecture of the Castillo de San Cristóbal. Though technically a castle, the Castillo de San Cristóbal is known as the oldest fort in Puerto Rico. Built in 1783 by the Spanish, the immense structure sits at the edge of the island rising 150 feet above the water, offering a dose of history along with scenic ocean views. The fortified castle helped stave off many invaders during various battles including an invasion by Sir Ralph Abercrombie in 1797, and features a unique architectural design with several layers, each fortified and walled to keep enemies out. We recommend walking through this Old San Juan fort to experience the intriguing layout first-hand.

Discover Old San Juan’s Rich Art Scene

Good news for art lovers, Old San Juan has a flourishing art scene with numerous galleries spread throughout the walled-in city. Stop by Galería Botello to study their collection of bronze sculptures, oil paintings and their unique wooden carved santos. The story behind Puerto Ricans’ interest in santos, or saints, is a tradition that dates back centuries. These small figurines carved in the liking of a preferred saint are used as offerings to which Puerto Ricans relay their prayers. You can find these santos at various galleries including the Siena Art Gallery or in smaller sizes at souvenir shops.


It’s always nice to have something to remember your experience in Old San Juan, so permit yourself to act like a tourist and take home a souvenir! Make a pit stop at Mascaras de Puerto Rico to shop for vejigante masks. Made of papier-mâché or coconut, these ornate masks originated in the 12th century in Spain and were worn in festivals celebrating victories in battle. These folkloric masks are an important part of Puerto Ricans’ arts and crafts culture, making it a suitable – though slightly frightful – souvenir to take home and hang up on your wall.

A must-see on your bucket list, Old San Juan, Puerto Rico is a Caribbean gem where visitors can discover a bounty of beautiful architecture, history, enticing cuisine, and art for all ages. Book your stay at a Hilton and enjoy your visit to Old San Juan, Puerto Rico!

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