Discover one of the oldest capitals in the Western Hemisphere, and explore Old San Juan’s colorful streets and historic plazas. Visit the 16th-century San Francisco de Asis Monastery, Plaza de Armas, UNESCO-recognized city walls along the turquoise water, and the Catedral de San Juan. Along the way, your expert local guide will reveal the island’s indigenous Taíno, African, and Spanish influences. Finish at Castillo San Felipe (El Morro), using a dedicated entrance for select tour groups for easy and seamless entry into Castillo San Felipe (El Morro). Small groups and a passionate guide make history come alive in just 2.5 hours. This tour conveniently starts a short 10-minute walk from Old San Juan Cruise Port and is ideal for cruise guests looking to see the highlights of San Juan with enough time to get to and from the boat.
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 the iconic fortress that has guarded San Juan for centuries. Explore its ramparts, tunnels, and sweeping ocean views while your guide shares stories of battles, pirates, and the city’s enduring spirit.
Please arrive 15 minutes prior to the start of your tour, your guide will be holding a green Walks sign. This tour meets in Plaza Arturo Somohano outside Teatro Tapia.
- Please arrive 15 minutes before your tour start time for check-in. Out of courtesy to other guests, we’re unable to wait for latecomers. No refunds can be provided for late arrivals or no-shows.
- The tour involves a fair amount of walking, and sometimes uneven terrain. Comfortable shoes are recommended.
- Areas visited during this tour are subject to closure. Your guide may need to modify areas visited on the day of the tour.
- Tips/gratuities (for your guide) are always appreciated.
San Juan, the capital and most populous city of Puerto Rico, is a vibrant blend of Spanish colonial history, Caribbean culture, and modern amenities. Known for its well-preserved historic sites, beautiful beaches, and lively nightlife, San Juan offers a unique tropical experience with a rich cultural heritage.
The historic heart of San Juan, known for its colorful colonial buildings, cobblestone streets, and historic sites.
The only tropical rainforest in the U.S. National Forest System, offering lush landscapes, waterfalls, and hiking trails.
A popular beach in the Condado neighborhood, known for its white sand, clear waters, and vibrant atmosphere.
A traditional Puerto Rican dish made from mashed fried plantains mixed with garlic, pork cracklings, and other ingredients.
Roasted pork, a staple in Puerto Rican cuisine, often served with rice and beans.
Fritters made from a mixture of green bananas, yautía (taro), and pork or crabmeat.
This is the dry season with warm, sunny weather and lower humidity. It's the best time for outdoor activities and beach visits.
U.S. Dollar (USD)
Atlantic Standard Time (AST), UTC-4
120VV, 60HzHz
San Juan is generally safe for tourists, but petty crime can occur. Be aware of your surroundings, especially in less touristy areas and at night.
Terminal de Carros Públicos de San Juan
Affordable and convenient, but schedules can be irregular. Trolleys are also available in Old San Juan.
Available • Apps: Uber, Lyft
Car, Bike, Scooter
A tropical rainforest offering lush landscapes, waterfalls, and hiking trails.
A coastal town known for its bioluminescent bay and water sports.
A small island known for its pristine beaches and relaxed atmosphere.
Price varies by option