Curator’s statement
My great-grandmother grew up in Old San Juan, Puerto Rico, before moving to the mainland as a young adult. Being able to experience what my great-grandmother once did and seeing the places in her stories is truly timeless. From reminiscing about funny stories of her setting up shop on Plaza de Armas to learning more about the history of Old San Juan, it made Old San Juan even sweeter to experience.
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Where to stay in Old San Juan
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Things to do in Old San Juan
Calle de la Fortaleza, known as “Umbrella Street”
Castillo San Felipe Del Morro: The historic fort that protected the port and Puerto Rico from the British. You will get to walk around the fort, see old quarters, where the cannons were placed, and learn about how the fort helped the Spanish defend their territory. The lawn of El Morro has a tradition of flying a kit.
La Fortaleza & Calle de la Fortaleza: Oldest Governor’s House. Along the road, you will be able to see the Calle de la Fortaleza, known as “Umbrella Street”.
Casa Blanca: A house museum and hotel, is the oldest house in Old San Juan. You can walk through where Ponce de Leon used to live and learn more about the 16th and 17th century.
San Cristobal Castillo: One of the largest forts in the Americas and was also a site for the “Pirates of the Caribbean: On Stranger Tides”.
Plaza Colon & Plaza de Armas: Not only does it have a ton of picture opportunities, it is the entrance plaza to Old San Juan. The statue in the middle is of Christopher Columbus as a memory of the Spanish arriving to the island. Plaza de Armas was the town square.
Puerta de San Juan: When walking the wall to the Castillo San Felipe Del Morro, you will either pass or enter through the Gate to Old San Juan. This served as the entrance to the city.
Parque de las Palomas: This park is next to the water where flocks of pigeons live. You can feed the pigeons out of the bag, your hand, or throw it on the ground.
El Yunque: A 45-minute drive from Old San Juan to visit the only rain forest in a United States national forest. You’ll get to see waterfalls, swimming holes, and beautiful plants and animals. There are many tour guides that you can book through.
Carabali Rainforest Park: UTV or Horseback riding through the rainforest and getting to swim in the Rio Grande. The tour guides are great at personalizing the tours even when multiple groups are together.
Casa Bacardi: A 23-minute drive from Old San Juan, worth it if you enjoy rum tasting. You can choose from different tour options around the property.
Places to eat & drink in Old San Juan
Anita Gelato
La Casita de Rones: Your one-stop shop for food, drinks, and shops, oh—and pictures. This is a great place to taste the rums of Puerto Rico.
Anita Gelato: When you need a sweet treat or a cool down, this is one of the best places to get gelato. The aesthetic and vibe makes it 10x more fun by feeling luxurious.
Tropical Taste: An authentic Puerto Rican restaurant hidden in the back of storefronts. The serving staff can help guide and navigate your taste through the menu to find your perfect match.
La Tortuga Bistro Bar: A laid-back bar and grill that has a mix of traditional Puerto Rican cuisine and American-style food.
Barrachina: Known for the “birthplace of piña colada” while also serving traditional and international cuisines.
Princesa - Cocina Cultura: A higher-end restaurant that dives into the history of Puerto Rico. Their menu focuses on 18th and 19th century cuisines.
Need to know
Recommend renting a Jeep if you plan to travel outside of Old San Juan. Roads are not the best and have a ton of potholes.
Bring lots of sunscreen if you plan to walk around.
Recommend walking the San Juan Wall to the Castillo San Felipe del Morro; however, it is directly in the sun and about a 1.25–1.50 mile walk, depending on where you start.
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Hannah Miller
Hannah Miller
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For more inspiration and insider recommendations, visit our San Juan page.