San Juan Bay - Our journey begins at the Waterfront Princess promenade. Take in the sights of San Juan Bay (Spanish: Bahía de San Juan), the main inlet next to Old San Juan. Stretching about 3.5 miles (5.6 km), it is the largest water body in an estuary covering roughly 97 square miles (250 km2) of channels, inlets, and eight interconnected lagoons. San Juan Bay hosts the island’s busiest harbor. Across the bay, you can see the stunning El Yunque, the Bacardi distillery, El Canuelo Fort, and Isla de la Cabra, a former leprosy colony.

Paseo de la Princesa - El Paseo de La Princesa, Puerto Rico’s most cherished promenade, dates back to 1853. This beautifully restored walkway is a favorite among locals day and night and attracts millions of visitors worldwide. Built in 1853, it allowed Victorian-era residents to stroll along the water. The ancient La Princesa jail, located outside the city walls, has original cells that are carefully preserved. Tours before 2 pm include entrance.

Old San Juan - Take a scenic walk along San Juan Bay, featuring impressive fortification walls leading to the RAICES monument, which represents Puerto Rico’s rich cultural heritage. Designed by Spanish artist Luis Sanguino, the Raices Fountain showcases Amerindian, African, and Spanish cultures. Discover ancient walls, garitas, and 1.9 miles of meticulously restored fortifications, a testament to Spain’s dominance in the New World.

La Puerta de San Juan - Visit the monument to Isabella II, the “walking trees,” and the original entrance to the Walled City - The Gate of San Juan. La Puerta de San Juan is the last of the five gates that provided access to the walled city of Old San Juan. The vibrant red gate, standing 16 feet tall, dates back to 1635.

Iglesia de San Jose - The colonial gem of the Americas, featuring 412 preserved colonial buildings, each with its own unique story. Cristo Street brings history to life with its beautiful walkways, numerous shops, and stunning views of Iglesia de San Jose, the second oldest church in the Americas, established in 1532 under Spanish rule. The church highlights the Gothic architecture of the time and was the resting place of Juan Ponce de León for 350 years, still bearing his coat of arms. Capilla del Cristo, Plaza las Palomas, the San Juan Cathedral, and Hotel El Convento are also located here.

Calle de la Fortaleza - Known as Umbrella Street, this acclaimed art project adds another amazing attraction in the heart of Old San Juan. Behind it is La Fortaleza, the official residence of the governor of Puerto Rico. Built between 1533 and 1540 to defend San Juan’s harbor, it is the oldest executive mansion in continuous use in the New World.

Plaza de Armas - Plaza de Armas, the main plaza of Old San Juan, features a unique blend of various architectural styles. Dating back to Spanish colonial times, it was designed as the city’s main town square. On one side of the plaza is San Juan’s official town hall building, and on another is the Puerto Rico Department of State. To fully enjoy Plaza de Armas, grab a coffee and a Puerto Rican pastry from any local spot. The plaza also features a skilled replica of Madrid’s Clock Tower.

Calle San Sebastian - Visit the community market for unique handcrafted souvenirs and vintage clothing made by local artists. Create your own memorable piece using a unique technique, a piece of art you’ll proudly display at home! Enjoy a single-origin coffee tasting, featuring coffee fit for popes and kings.

Catedral Basilica Menor de San Juan Bautista - The Catedral Basilica Menor de San Juan Bautista has been the cradle of Catholic faith for islanders for half a millennium. It is here that John Paul II performed the Holy Service.