San Juan

15 Best Old San Juan Walking Tours

The walking tours through five centuries of Old San Juan: blue cobblestones that arrived as ship ballast, El Morro’s ramparts and balconies in paint-box colors. The oldest city under the US flag, covered in two miles.

1.Old San Juan Walking Tour

Discover Old San Juan's vibrant streets and historic sites on this 2-hour guided walking tour with expert guide David Rodríguez, offering deep insights and authentic charm for just $39.

Most Popular★ 5.0

“It is a great tour filled with so much history and information about Old San Juan. It’s was such a beautiful experience.”

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2.Old San Juan City Walking Tour

Discover Old San Juan's charm on a 2-hour guided walking tour. Learn history, see landmarks, and enjoy a personalized experience for just $39.

★ 5.0

“Fantastic - Carlos was a superb guide. We saw all the major attractions. Tour was paced very well. Highly recommend. He gave lots of local dining and entertainment recommendations.”

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3.Old San Juan: Segway PT and Segway Xafari Ebike Tours

Discover Old San Juan on a lively 2-hour Segway tour, visiting over 25 historic sites with expert guides. Perfect for those seeking fun, history, and scenic views.

★ 4.5

“We did this tour a few years back on a cruise, liked it that time we did it again. It was changed up a bit from the last experience. Personally I think it was better because last time it was a group of 8. This…”

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4.Historic Old San Juan Sunset Walking Tour

Discover Old San Juan's charms on a 2-hour sunset walking tour, featuring iconic sites, stunning views, and expert guides for an authentic experience.

★ 5.0

“Antonio is exceedingly warm and full of facts., not to mention bilingual and insightful. While there is plenty to say and learn about old San Juan, he was gracious about taking many questions that came up from his fascinating comments. I Read more”

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5.Old San Juan Bar Crawl: Experience Local Hotspots

Explore Old San Juan's vibrant nightlife on this 3-hour pub crawl for $65. Enjoy free drinks, local tapas, lively guides, and authentic Puerto Rican vibes.

★ 4.5

“They were very kind and helpful it was fun. Very great deals on drinks and a great group experience. We went to a bar with unlimited drinks I would definitely do it again”

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

Experience Old San Juan’s flavors and history on a 3-hour sunset food tour with up to five authentic stops, guided by passionate locals and full of flavor.

★ 5.0

“Dezi was a perfect host walking us around Old San Juan! The food and drinks were excellent albeit a lot of food. (Not complaining.) her knowledge of Puerto Rico enlightened us about her country. Do yourself a favor favor and take this tour of you…”

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

Discover Old San Juan with a guided tour covering historic landmarks, shopping, and local cuisine. Enjoy expert insights in a comfortable half-day experience.

★ 4.5

“Tour guide Michelle was friendly, knowledgeable and made the tour enjoyable. It was great to visit historical places and eat tasty treats.”

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10.3 Tours in 1 Day: Old San Juan, Rainforest, Beach with Transport

Discover Old San Juan, explore El Yunque Rainforest, and relax on Luquillo Beach—all in one guided day tour with transport, for a full Puerto Rican experience.

★ 5.0

“My daughter and I had an amazing time! It was full of adventure, excitement, and a lot of local info! The rainforest and waterslides were our favorite! Highly recommended.”

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11.Old San Juan Historical Walking Tour

Discover San Juan’s historic charm on a guided walking tour exploring iconic sites, hidden gems, and local stories for an authentic Puerto Rican experience.

★ 5.0

“Great introduction to the city of San Juan. Danny was excellent in informing us of all the history of the city.”

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12.FlyDining: Sunset & City Lights Dinner Over Old San Juan

Experience dinner over Old San Juan from 130ft high with panoramic views, gourmet food, and lively atmosphere—perfect for special occasions and thrill-seekers.

★ 4.5

“I am TERRIFIED of heights.... But who else can day they had Thanksgiving Dinner at 130ft? A couple margs and the height is not even an issue. The staff are so friendly and it's a smooth operation. Andrea and the photograph dude are awesome!”

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13.Morning Old San Juan Food Tour

Explore Old San Juan through a 3-hour guided walking food tour, tasting local dishes, sipping rum, and discovering historic sights with a friendly guide.

★ 5.0

“I believe we made four stops, and at each were offered a beverage and food(s), plus lots of interesting history about the city, the food and the culture”

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15.Explore Old San Juan Walking Tour

Discover Old San Juan with a knowledgeable guide on this 2-hour walking tour, exploring historic sites, secret spots, and stunning views for just $30.

★ 5.0

“Harry was very knowledgeable and experience. He prompted for questions throughout the tour. A very enjoyable activity with exercise to last for weeks.”

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