Begin the tour in the heart of Old San Juan at Plaza de la Catedral, one of the oldest and most historic plazas in the city. Here we’ll take a few minutes to introduce ourselves, get to know the group, and set the stage for the experience ahead. While surrounded by centuries-old architecture, you’ll learn about the origins of Old San Juan and the role this plaza has played in the city’s history.

Learn the history of catedral San Juan Bautista.

Step inside the historic Hotel El Convento, a beautifully preserved former convent that dates back to the 1600s. Here we’ll visit a coffee shop and local food market located inside the hotel to enjoy Puerto Rican coffee while learning about the island’s agricultural traditions, including coffee, sugarcane, and tobacco.

Stop at the famous La Rogativa sculpture overlooking San Juan Bay while discovering the stories behind Old San Juan’s defensive walls and harbor. From this scenic viewpoint you’ll see landmarks such as La Fortaleza, the governor’s residence and UNESCO World Heritage Site, Casa Blanca, the oldest structure in Old San Juan, and the Bacardí Rum Distillery across the bay. You’ll also enjoy beautiful views of the harbor and the distant Cordillera Central mountains, and may even spot the famous cats of Old San Juan.

As we make our way toward La Perla, we’ll pass by the famous Castillo San Felipe del Morro, one of the most iconic fortresses in the Caribbean and part of the San Juan National Historic Site. Along the walk you’ll enjoy views of the dramatic coastline and see other historic landmarks that help tell the story of Old San Juan.

Visit the iconic oceanfront community of La Perla, located just outside the historic city walls. This is where we’ll enjoy our main Puerto Rican food tasting, dining at a beautiful local restaurant with views of the Atlantic Ocean. Taste traditional comida criolla such as mofongo while learning how Taíno, African, and Spanish influences shaped Puerto Rican cuisine. We’ll also walk along La Perla’s famous malecón, hear the story of this unique neighborhood, and see Old San Juan’s historic walls from a completely different perspective.

Stop on this lively street to taste traditional Puerto Rican fritters such as alcapurrias or empanadillas while enjoying a cold local beer and learning about the island’s vibrant street food culture.

End the tour on Calle San Sebastián, one of the most lively and historic streets in Old San Juan. Here we’ll wrap up the experience with a refreshing mojito, while learning about the famous Fiestas de la Calle San Sebastián, the largest cultural festival in the Caribbean.