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

“Tour with David, our guide, began promptly as scheduled at the designated meeting place & was initially carded to be of 2hrs & 15 minutes duration but actually lasted closer to 2 1/2 hrs. That time was fully packed with information & explanations about all…”

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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

“Take water with you, comfortable shoes. It was a great tour. Carlos was knowledgeable but relaxed and personable.”

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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

“Good and very informative. Guide was helpful informant. Be prepared for some bumpy spots on the old cobblestone. You’ll see primarily old San Juan. Happy we did it. Remember to put on sunscreen and dress for warm temperatures.”

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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

“It was a great way to see different places and explore old San Juan. I wish there was more of an opportunity to meet the people in our group and see more places. I would definitely do this again if it was a longer experience…”

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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

“⭐️⭐️⭐️⭐️⭐️ Savor the Sunset: Viejo San Juan Food Tour with Pablo Garcia (Spoon Tours) My daughter and I joined the Savor the Sunset tour with Pablo Garcia, and it was absolutely incredible! We visited four unique establishments, each offering authentic Puerto Rican cuisine and refreshing…”

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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

“The company was outstanding with communication. I have never experienced anything like it while preparing for a tour. Text messages and answering phone calls. Unfortunately the transportation Van's AC was not adequate. It was a hot day in Puerto Rico. Gabriel was a super guide…”

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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

“The staff was very entertaining and it was something to remember. The food was ok and the drinks could have been better. It’s good to try once but the menu needs some updating. Also would’ve been good to have additional selections.”

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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

“Lorna was the best tour guide! She got to know all of her guests and made the tour feel so personalized to each of us. She was extremely knowledgeable and fun! I highly recommend her!”

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