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

“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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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

“Very informative and helpful to do on your first day in PR!! Our tour guide took us around old San Juan and showed us the best places to shop and eat.”

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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

“Nico was a fantastic guide for this tour. She was incredibly knowledgeable and welcoming. I expected a couple more stops for the price, but the food we did have was amazing and we learned a lot about the history of Puerto Rico and the food…”

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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

“Our guide Gwen was wonderful. She was informative and interesting. She also gave great suggestions for local places to visit. We highly recommend taking this tour!”

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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

“Overall the experience was ok. The sunset view was amazing! That was my favorite part. The mahi mahi filet was good. I would recommend making sure there’s salt and pepper on board instead of just hot sauce. The ice cream and cookies want the best.…”

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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

“Wiki Pablo was Excellent!! So much information, facts…etc! Very knowledgeable!! Fun Personality!! And … a nice sampling of Puerto Rican food. Thank You for this excellent experience!!”

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14.Make Your Own Perfume Guided Workshop | Old San Juan

Create your own signature perfume in a fun, hands-on workshop in Old San Juan. Personalized, engaging, and perfect for gift-giving or memories.

★ 5.0

“This was a great way to spend a rainy evening. Our Perfumer Fabiola (Fabi) was absolutely delightful and a pleasure that helped us with choosing the best fragrance. My Daughter and I had fun doing this activity together. Highly recommend this to break up the…”

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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

“Eli was a great guide. He took the time to respond to questions. The path we took was a great intro to old San Juan. It really provides a great explanation of the evolution of the island. I am so happy that I booked this!”

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