The 10 Best Things to See and Do in Old San Juan

by Donna Heiderstadt

The 10 Best Things to See and Do in Old San Juan

by Donna Heiderstadt

Old San Juan was founded back in 1521. Fast-forward (almost) 500 years, and Old San Juan has since become one of Puerto Rico’s most-visited sights — and one of the Caribbean’s most vibrant neighborhoods. Here are 10 things to see and do when in town, according to our expert.

Old San Juan was founded back in 1521. Fast-forward (almost) 500 years, and Old San Juan has since become one of Puerto Rico’s most-visited sights — and one of the Caribbean’s most vibrant neighborhoods. Here are 10 things to see and do when in town, according to our expert.

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Old San Juan / dennisvdw/iStock
Castillo San Felipe del Morro
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Castillo San Felipe del Morro (El Morro)

Castillo San Felipe del Morro (also known as El Morro) took over 250 years to construct and features six levels. It’s a UNESCO World Heritage Site (as is all of Old San Juan) and a great place to explore on a sunny day —don’t miss the views from the top level.

Castillo San Felipe del Morro (also known as El Morro) took over 250 years to construct and features six levels. It’s a UNESCO World Heritage Site (as is all of Old San Juan) and a great place to explore on a sunny day —don’t miss the views from the top level.

Paseo de la Princesa
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Paseo de la Princesa (Walkway of the Princess)

Paseo de la Princesa is a beautiful promenade that dates back to 1853. Lined with vintage lampposts, it begins in a tree-shaded park of the same name and winds its way around the city’s southern wall and offers splendid views of San Juan Bay and El Morro. Along the way, you’ll pass La Puerta de Old San Juan (San Juan Gate), the city’s sole remaining historic gate.

Paseo de la Princesa is a beautiful promenade that dates back to 1853. Lined with vintage lampposts, it begins in a tree-shaded park of the same name and winds its way around the city’s southern wall and offers splendid views of San Juan Bay and El Morro. Along the way, you’ll pass La Puerta de Old San Juan (San Juan Gate), the city’s sole remaining historic gate.

Shrimp mofongo
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Try Mofongo

Make the island’s national dish — garlic-flavored mashed plantains typically served with shrimp, pork, beef, or chicken — your lunch of choice. You’ll find many restaurants serving it in Old San Juan (Restaurante Raices serves generous portions, but El Jibarito is also highly recommended). Wash it down with a glass of white sangria. 

Make the island’s national dish — garlic-flavored mashed plantains typically served with shrimp, pork, beef, or chicken — your lunch of choice. You’ll find many restaurants serving it in Old San Juan (Restaurante Raices serves generous portions, but El Jibarito is also highly recommended). Wash it down with a glass of white sangria. 

Cathedral of San Juan Bautista
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Catedral de San Juan Bautista (Cathedral of St. John the Baptist)

This elegant, yellow-hued landmark was constructed back in 1540, and it's the second-oldest church in the Western Hemisphere. Today, it's a sought-after wedding venue (you’re almost certain to see a bride on weekends). Afterwards, enjoy a cocktail at the atmospheric Hotel Convento, which is located right across the street. 

This elegant, yellow-hued landmark was constructed back in 1540, and it's the second-oldest church in the Western Hemisphere. Today, it's a sought-after wedding venue (you’re almost certain to see a bride on weekends). Afterwards, enjoy a cocktail at the atmospheric Hotel Convento, which is located right across the street. 

Condado
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Bike Ride to Condado

Pedal your way from Old San Juan to Condado (a hotel-lined, beachfront neighborhood with great restaurants and nightlife) while visiting a few historic sights along the way. Rent the Bicycle in Old San Juan offers a three-hour guided tour with stops at San Cristobal Fortress, Condado Lagoon, and Santurce Marketplace, where you can enjoy a refreshing snack.

Pedal your way from Old San Juan to Condado (a hotel-lined, beachfront neighborhood with great restaurants and nightlife) while visiting a few historic sights along the way. Rent the Bicycle in Old San Juan offers a three-hour guided tour with stops at San Cristobal Fortress, Condado Lagoon, and Santurce Marketplace, where you can enjoy a refreshing snack.

Santurce Market
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La Placita de Santurce (Santurce Marketplace)

This colorful square — which is technically located outside of Old San Juan, on the edge of neighboring Condado — houses the historic daytime Mercado de Santurce, where you'll find fresh fruits, vegetables, and refreshing smoothies. Come nighttime, the square transforms into a vibrant street party with al fresco salsa and merengue music along with icy mojitos. 

This colorful square — which is technically located outside of Old San Juan, on the edge of neighboring Condado — houses the historic daytime Mercado de Santurce, where you'll find fresh fruits, vegetables, and refreshing smoothies. Come nighttime, the square transforms into a vibrant street party with al fresco salsa and merengue music along with icy mojitos. 

Castillo San Cristóbal
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Castillo San Cristóbal

If it’s two forts for the price of one, why not? A ticket to El Morro also grants access to Castillo San Cristóbal (within 24 hours of purchase). Castillo San Cristóbal is named for St. Christopher (the patron saint of travelers) and was completed in 1783 after 150 years of construction. Today, it remains the largest fortress in the Americas. There’s even a dungeon with drawings made by an 18th-century prisoner.

If it’s two forts for the price of one, why not? A ticket to El Morro also grants access to Castillo San Cristóbal (within 24 hours of purchase). Castillo San Cristóbal is named for St. Christopher (the patron saint of travelers) and was completed in 1783 after 150 years of construction. Today, it remains the largest fortress in the Americas. There’s even a dungeon with drawings made by an 18th-century prisoner.

 Calle de la Fortaleza
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Calle del Cristo and Calle de la Fortaleza

These two streets (among the most photogenic in Old San Juan) are lined with colonial-era buildings painted in bright Caribbean hues that house bars, restaurants, shops, and galleries. A stroll here offers a chance to snap photos, sip mojitos, and even pick up a souvenir or two. 

These two streets (among the most photogenic in Old San Juan) are lined with colonial-era buildings painted in bright Caribbean hues that house bars, restaurants, shops, and galleries. A stroll here offers a chance to snap photos, sip mojitos, and even pick up a souvenir or two. 

La Casa Blanca
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La Casa Blanca

Explorer and conquistador Juan Ponce de Léon began building this house shortly before he died in Cuba in 1521. While he never lived here, his descendants did for two centuries. Today, La Casa Blanca remains one of the oldest on the island, and it's now home to a museum. 

Explorer and conquistador Juan Ponce de Léon began building this house shortly before he died in Cuba in 1521. While he never lived here, his descendants did for two centuries. Today, La Casa Blanca remains one of the oldest on the island, and it's now home to a museum. 

La Rogativa
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La Rogativa

Created in 1971 by New Zealand artist Lindsay Daen, this 12-foot bronze statue depicts a group of people making a plea to God for help. It commemorates the true story of Old San Juan’s bishop leading a crowd of women through the streets one night in 1797 — an act that caused invading British troops to retreat. It’s located on Caleta de las Manjas near the San Juan Gate.

Created in 1971 by New Zealand artist Lindsay Daen, this 12-foot bronze statue depicts a group of people making a plea to God for help. It commemorates the true story of Old San Juan’s bishop leading a crowd of women through the streets one night in 1797 — an act that caused invading British troops to retreat. It’s located on Caleta de las Manjas near the San Juan Gate.

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