Step into the heart of Old San Juan and uncover Puerto Rico’s 4,000+ year story on this 2.5-hour tour. From the moment you meet your local guide, you’ll wander cobblestone streets lined with colourful colonial houses, hear tales of the island’s indigenous Taíno, African, and Spanish influences, and discover how these cultures shaped Puerto Rico’s identity.

The first stop is at Plaza Colón, where the Commemorative Fountain marks Columbus’ arrival in 1493. From there, visit the 16th-century San Francisco de Asis Monastery, including its hidden crypt, to learn how early Spanish settlement began and meet some of the historical figures buried there. Stroll through charming Plaza de Armas, the original town square, where the colonial houses and fountains reveal its Spanish influence. Continue along the UNESCO city walls, including the Bastión de las Palmas, where your guide will recount historic battles that defended Puerto Rico and why the island has been called the “gateway to the New World.” Pass by La Casa Estrecha, and explore the Catedral de San Juan, the second-oldest church in the Americas. Finish at the Castillo San Felipe (El Morro), the 16th-century fortress that once defended the island. Explore its ramparts, hear stories of pirates and battles, and enjoy breathtaking views of the Atlantic.

With a small group of 15 guests or fewer, this tour ensures a personal, immersive experience, letting you connect with the history and culture of Old San Juan.