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 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.

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. 

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. 

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.

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. 

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.

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. 

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. 

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.