San Juan

15 Best Old San Juan Walking Tours

I walk Old San Juan with every guest I host, and these guided tours beat my amateur route every time. The blue tinted cobblestones arrived as ship ballast centuries ago. A good guide ties them to five centuries of sieges, pirates, and rum.

1.Old San Juan Walking Tour

Discover the hidden secrets of Old San Juan on a walking tour, where each step unveils captivating stories and deepens your understanding of this enchanting Caribbean gem.

Most Popular★ 5.0

“Our tour was closer to three hours, not two, but our tour guide, David, was great. I had a really nice time and felt like I got a really good overview of San Juan.. a great way to get some exercise and to learn about…”

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2.Old San Juan City Walking Tour

Step into the captivating world of Old San Juan on the City Walking Tour and uncover the hidden stories and vibrant culture that lie within its ancient streets.

★ 5.0

“This tour was a fantastic way to start our vacation! We went straight to the tour from the airport. Carlos was very knowledgable, friendly and made it a fun day. We got rained on a few times, but took the breaks needed before we kept…”

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3.Historic Old San Juan Sunset Walking Tour

Discover Old San Juan’s charm during a 2-hour sunset walking tour, with expert guides, stunning views, and insider tips perfect for first-timers and history lovers alike.

★ 5.0

“Melanie was such a fun guide and really made our experience seem like it was designed just for us. She was very knowledgeable and you can tell she just has such a passion for her culture and history! We got to see so many great…”

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5.Old San Juan Sunset Walk & Taste Food Tour

Keen travelers embark on a captivating culinary adventure in Old San Juan, where tantalizing flavors and hidden gems await, leaving them hungry for more.

★ 5.0

“Gia was just spectacular!!! So friendly, knowledgeable and sweet! We just had the BEST tour with her. We ate like royalty, and had so much fun along the way! 10 stars if we could give them!”

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7.Old San Juan Golf Cart Exploration ( Est. )

Yearning to discover a new side of Old San Juan? Embark on an unforgettable golf cart exploration that promises hidden gems, intriguing stories, and a personalized adventure like no other.

★ 4.5

“Excellent in every way. Chris was a wonderful guide. Highly recommend. Take the 9am tour for a less crowded experience.”

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

Experience the best of Puerto Rico in a single day with this 3-in-1 tour covering Old San Juan, El Yunque rainforest, and Luquillo Beach, all with transport included.

★ 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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10.Old San Juan Walking Historical Tour

Never before have you experienced the rich history and vibrant culture of Old San Juan like this, join us on a walking tour that will leave you wanting more.

★ 5.0

“Our guide Naomi was great! She knew San Juan and its history very well. It was so interesting! She was very personable and even gave recommendations for where to get lunch, gelato, and pina coladas! We highly recommend her!”

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

Experience a thrilling dinner suspended high above Old San Juan, with stunning sunset and city lights views, gourmet cuisine, and a lively atmosphere.

★ 4.5

“This is an once in a life time experience. The staff was amazing. The food was amazing. The vibe was outstanding. The staff makes you feel comfortable even when you’re scared. All in all I would do it again”

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12.Morning Old San Juan Food Tour

Discover Old San Juan’s charm on this 3-hour food and history tour, featuring local bites, drinks, and stunning colonial architecture with expert guides.

★ 5.0

“Sue was absolutely amazing! The detailed history of Puerto Rico was super amazing. The food was delicious! It was nice meeting new people that were visiting!”

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