Walking Tours

SAN JUAN

Best Walking Tours In San Juan

Ranked by traveller popularity

The 10 most popular walking tours in San Juan. Here's what they actually deliver, who runs them, and what they cost.

10 Best Walking Tours In San Juan

Old San Juan Walking Tour

Old San Juan Walking Tour - From Plaza Colón to La Puerta de San Juan: Streets With Purpose

1.Old San Juan Walking Tour

Most Popular 5.0

Old San Juan walking tour with writer David Rodríguez. Small-group stroll to walls, plazas, churches, and waterfront views for $39.

“The guy was very insightful. He was very knowledgeable about the history and gave us great pointers after the tour for restaurants.”

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Old San Juan City Walking Tour

Old San Juan City Walking Tour - What the Guide Actually Does With the 500-Year Story

2.Old San Juan City Walking Tour

5.0

A 2-hour small-group walk through Old San Juan with a certified guide, 500 years of context, and standout photo stops for $39.

“Carlos was great and very informative! We were so happy we decided to do the tour. I highly recommend! Be sure to wear your walking shoes…”

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Historic Old San Juan Sunset Walking Tour

Historic Old San Juan Sunset Walking Tour - Plaza de la Barandilla: residential and commercial architecture, unchanged in feel

Savor the Sunset: Old San Juan Walking Food Tour

Savor the Sunset: Old San Juan Walking Food Tour - Finding the group: Plaza de Armas and the 4:00 pm start

4.Savor the Sunset: Old San Juan Walking Food Tour

5.0

Sunset walking food tour in Old San Juan with up to 10 tastings, two cocktails, and a small-group guide for history and great local bites.

“Tour guide did a fantastic job interesting and informative but was doing a lot of coordination of the tour on the fly. Not the fault of the guide at all but for the money spent didn't feel the value was there. Would recommend this at half the price. We did have some wonderful bites and…”

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Old San Juan and El Morro Castle Walking Tour

Old San Juan and El Morro Castle Walking Tour - Meeting at La Casita de Rones: find the fountain, not the crowd

5.Old San Juan and El Morro Castle Walking Tour

5.0

Walk Old San Juan’s key landmarks with a bilingual local guide, then enter El Morro Fort for 16th-century Spanish–US military stories.

“This tour was worth every cent. Maria was a wonderful guide. She was knowledgeable and personable. The tour gave us a lovely insight into the rich history and culture of Puerto Rico that truly enhanced our appreciation for the island and it's people.”

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Old San Juan Historical Walk, Shopping, and Dining w/ Transport

Old San Juan Historical Walk, Shopping, and Dining w/ Transport - Walking the City Walls: What You Actually See (and Why It Feels Different)

Old San Juan Historical Walking Tour

Old San Juan Historical Walking Tour - Stop 1: La Casa Estrecha and the story behind San Juan’s tight streets

7.Old San Juan Historical Walking Tour

5.0

A 2-hour Old San Juan walking tour for up to 18 people, with free-entry stops, expert guide stories, and a great first-trip orientation.

“Daniel was incredible. This was one the best tours I have ever had. He knows everything about everything in San Jaun and if he doesn’t he knows the person who does. This tour made my trip.”

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Explore Old San Juan Walking Tour

Explore Old San Juan Walking Tour - Castillo San Felipe del Morro: what you’ll notice even without buying entry

San Juan Haunted History Walking Tour

San Juan Haunted History Walking Tour - Price and value: what $44.99 gets you (and what it does not)

9.San Juan Haunted History Walking Tour

4.0

A 2–2.5 hour haunted history walk in Old San Juan with landmark stops, local legends, and night-only cemetery and fort stories.

“I respect the management of this company sincerely. I booked a group tour as a solo, but the other group wound up canceling. I was going to be the only person on a group rate event! Instead of canceling to maximize profits, they honored my reservation bc they felt it was the right thing to…”

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Old San Juan Walking Tour with a Local Certified Guide

Old San Juan Walking Tour with a Local Certified Guide - Castillo de San Cristóbal: the fort you’ll understand better after the tour

10.Old San Juan Walking Tour with a Local Certified Guide

5.0

Old San Juan walking tour with a certified local guide: forts, city gates, plazas, and history in about 2 hours for $25.

“Lovely tour with Danny! He is very knowledgeable on the history of Puerto Rico, kept us in the shade as much as possible during our tour, gave restaurant and areas to visit recommendations and was ready with mini water bottles!”

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