Stop 1 — Choose one option: Option A: Castillo San Felipe del Morro — Explore the iconic 16th-century citadel standing guard over the entrance to San Juan Bay. Walk through its massive ramparts, sentry boxes (garitas), and multi-tiered ocean-side defenses.

Option B: Castillo San Cristóbal — Discover the largest fortification built by the Spanish in the New World. Walk the expansive main courtyard, dark tunnels, and the strategic outpost that protected the city from land-based attacks.

Stop 2 — Choose one option: Option A: Plaza de Armas & City Hall — Stroll through the historic main square of Old San Juan. View the beautiful 19th-century four-seasons fountain and admire the classic architecture of the Alcaldía (City Hall).

Option B: Plaza de Colón & San Justo Streets — Begin at the grand square featuring the statue of Christopher Columbus. Walk along the vibrant cobblestone streets, taking in the pastel-colored colonial buildings and unique blue adoquín pavers.

Stop 3 — Choose one option: Option A: San Juan Bautista Cathedral & El Convento — Step inside the oldest cathedral in the United States to view the tomb of explorer Juan Ponce de León, followed by a walk past the historic, majestic Hotel El Convento.

Option B: Capilla del Cristo & Puerta de San Juan — Visit the legendary 18th-century chapel built on top of the city walls, then walk down to the massive red sandstone gate that served as the primary historic entry point to the city.