Wander through the cobblestone streets of Old San Juan, where vibrant colors, Spanish colonial architecture, and Caribbean flair blend into one unforgettable scene. As you explore, you’ll hear fascinating stories of conquistadors, pirates, and the island’s transformation through the centuries. Discover how Spanish traditions and American influences come together in this historic district — from its pastel facades and wrought-iron balconies to the lively plazas that capture the spirit of Puerto Rico

Pause in this lively square beneath the statue of Christopher Columbus and hear how Old San Juan’s story began. Discover the plaza’s colonial past, local legends, and the energy that still makes it a favorite meeting spot today

Step inside this 16th-century monastery to uncover one of Old San Juan’s hidden gems. Explore the crypt below and hear the fascinating stories of the historical figures who rest here

Casa Estrella & San Juan’s Quirky Homes See one of Old San Juan’s most eye-catching houses, where bright colors and unusual design capture the city’s playful spirit. Learn how these iconic homes reflect the creativity and character that make San Juan so unforgettable

Step inside one of the oldest churches in the Americas, a serene masterpiece that’s still at the heart of local life. Admire its centuries-old architecture and discover the stories of faith, resilience, and devotion that shaped Puerto Rico’s history.

Pause at the city’s original main entrance, where travelers once arrived by sea to the “Walled City.” Walk through the same gate that welcomed explorers, merchants, and governors centuries ago, and imagine the bustling harbor that lay beyond.

Experience the lively heart of Old San Juan at its historic main square. Surrounded by colonial buildings and shaded fountains, this plaza has been the city’s meeting place for more than 500 years — perfect for people-watching and soaking up local life.

Finish your tour at Castillo San Felipe (El Morro), the 16th-century fortress that defended the island for centuries. Your guide provides your entrance tickets and then gives you free time to explore its ramparts and take in the panoramic views of the Atlantic.