Old San Juan Historical Walking Tour

Wow, I was completely blown away by the caliber of this tour. I’m an experienced traveler and have had countless tours ranging from free to expensive, and this was easily one of the best. Leslie’s knowledge is extensive and she did a great and entertaining job of weaving historical details with contemporary information ranging from social and political, to economic. She’s very flexible to the type of experience the group is looking for and their questions/interests. Intelligent, enormously knowledgeable, and entertaining. I want to take her other tours now!

Wow, I was completely blown away by the caliber of this tour. I’m an experienced traveler and have had countless tours ranging from free to expensive, and this was easily one of the best. Leslie’s knowledge is extensive and she did a great and entertaining job of weaving historical details with contemporary information ranging from social and political, to economic. She’s very flexible to the type of experience the group is looking for and their questions/interests. Intelligent, enormously knowledgeable, and entertaining. I want to take her other tours now!

Our guide, Jesus, was super knowledgeable about the history, traditions, and politics of Puerto Rico. Super high energy guy; you can tell he’s passionate about Old San Juan. There were some logistics issues outside of his control, and he handled it like a pro! Still made sure the tour was fun for everyone. Gave us great recommendations for food and nightlife, for those who want that authentic San Juan experience. Also, if you’re into basketball and other sports, he’s your guy.

Diego was a great guide and the stops her perfect picks! My husband and I have done quite a few food tours in different countries and we agreed that this one made the top of the list! Cannot recommend this tour enough if you are visiting OSJ

10/10 experience!! Claudia was extremely knowledgeable, easy going and just a fun person to have guided us through old San Juan. We absolutely loved her and the tour itself was so informative. I’ve been here 5 times and she taught us so much we never knew about. I would highly recommend this tour to everyone!!

Andres was so friendly, personable, and knowledgeable. He took us at a comfortable pace finding spots in the shade to rest and share the history of Puerto Rico. We had a terrific time and would use this company again!

Very pleasant stroll through Old Town San Juan Puerto Rico with a very knowledgeable tour guide, Carola.

Great value for the money spent. So much food and a great variety was offered throughout the tour. I was so full at the end I barely had room for dessert and had to take it to go! I would advise anyone participating in this tour to hold off and not eat a full breakfast.

What a great tour! The meeting spot was super easy to find, our guide, Nahiomy, was early but gave us space to just hang out before the tour started. It turned out to be a small group of 4 which made the tour feel personalized. It was an extremely hot day but Nahiomy was so good about stopping in shady spots to talk about the buildings and statues and what not. Nahiomy’s English was phenomenal! We could understand her completely and boy was she informative!!! I don’t know how she holds all of that knowledge in her brain! Her manner of speaking and enthusiasm to tell us about the Old City made it clear that being a tour guide & teaching others about her island is her passion. I wouldn’t call the walk strenuous but be sure to wear either good walking sandals or socks & sneakers. Avoid flip flops. Bring lots of water. There were two bathrooms breaks at which we had the opportunity to buy water or shaved ice if we needed it. I would absolutely book this tour again!

Lesley Ann was knowledgeable and personable. She was a great guide. Her knowledge was exceptional. I would request her again.

Pablo was fantastic. He was incredibly knowledgeable and gave great local recommendations.

Our guide was amazing. She gave us great history of old San Juan, she made the tour personal

We had an amazing tour of the Old San Juan Historic District with Carola from Flavors of San Juan! Carola was incredibly knowledgeable, engaging, and passionate about Puerto Rico’s history and culture. She brought the city’s fascinating past to life while sharing interesting stories and local insights that made the experience unforgettable. The tour was well-paced, informative, and fun. I highly recommend this tour to anyone visiting San Juan and looking for an authentic, memorable experience. Thank you, Carola, for a fantastic day!

Naomi was fantastic! She was funny, knowledgeable and the pace of the tour was perfect!

We loved our historical walking tour of Old San Juan! Our guide, Leslie, was very knowledgeable about the history and architecture of Old San Juan, and she was also super funny and entertaining. We had such a good time learning about the buildings, the streets, the statues, and the history - Leslie even taught us about the pop culture of Puerto Rico! I would highly recommend this tour to adults or families with teenagers. Our family of 4 had a great time!

Pablo was an amazing tour guide! So thorough and engaging the whole time. He answered all of our questions and was extremely knowledgeable

Danny did a great job! His passion and excitement showed as we toured Old San Juan learned of the history and what made Old San Juan what is it. Tasted delicious authentic flavors along the way. Appreciated the energy and knowledge of Danny. Very interesting tour with great food tastings along the way.

My husband and I took this 2-hour walking tour of Old San Juan, and it was a wonderful experience. Our guide, Claudia, was incredibly passionate and brought the history and culture of the city to life. She shared fascinating stories and made the tour both informative and enjoyable. At the end of the tour, she also gave us excellent recommendations for local restaurants and shopping, which made the rest of our day even better. I highly recommend this tour to anyone visiting Old San Juan!

Our guide, Alberto was very kind and clearly LOVED his job. He knew tons about the city and made this a great tour. We laughed, learned and had a great time.

Very knowledgeable on the history of old San Juan

Our guide Pablo was a total delight to spend time with. I learned a ton of new things and saw part of San Juan id never been too before. If I could give him 20 stars I would.

This tour was amazing. Raisa was our guide, and she taught us so much about old San Juan. History was divided into 3 pieces: before the arrival of the Spaniards, during Spanish rule, and under American rule. I loved the way she explained everything, throwing in a joke here and there. I’m very detail oriented and like to get what I pay for: this tour was absolutely worth the cost. Additionally, the tour says no bathroom breaks, but if you really need to go don’t worry; she gives two 10 minute breaks throughout the tour to go to the bathroom, take a closer look at the sights, or grab a water. The walk itself was also not too extrenuating; we had some people who were not at peak health and they were okay. Raisa also stops here and there to speak, which gives people an opportunity to sit down. A huge thank you to the tour company for letting us move tour dates at no cost!

This was a well put together tour. The tour guide was very informative and educated on the history of Puerto Rico.

Leslie was informative and engaging! I traveled to Puerto Rico with a group of students for a summer travel course from Lycoming College and the students really benefited from Leslie's informative tour which was tailored to their specific interests. Such a wonderful and generous way to operate the tour!

Alberto was our tour guide and he made the tour fun and interesting. He’s extremely knowledgeable and has a passion for history and his country- you won’t go wrong if you book with Alberto. I did the 5-7 walking tour and it was lovely to spend the evening strolling the streets seeing the activity while learning about the culture and history- 2 hours was perfect allotted time with a break in between to get a beverage of your choice and sit for a minute. Really enjoyed it!!! Book with Alberto!!

Our guide contacted us the day before the tour with clear instructions and details, which made everything very easy and stress-free. We learned a lot about the history of Old San Juan, especially the wall surrounding the city and its significance. I also appreciated that the tour helped us discover places we later returned to on our own during the trip. The guide was knowledgeable, engaging, and made the history feel very accessible. Overall, it was a great introduction to Old San Juan and Puerto Rican history.

I loved how informative and knowledgeable Carola was while keeping it fun and interesting. I highly recommend this tour.

Naihomy was our guide, and despite it being only the 2 of us, she provided a top notch tour. I was a bit under the weather due to the heat and high humidity, and she kindly kept the tour educational and shaded as much as possible. Great tour to take!

The tour was great. Miguel from food fla vors tour was very knowledgeable and showed us a great tour.

A nice paced and informative two hour tour. We have been to Puerto Rico before but didn't know much about the history. Riza pointed out things we never would have noticed on our own. She gave us some personal insights and certainly gave us some ideas for where to explore more on our own. It was thoroughly enjoyable!

The walking tour was fantastic! My Apple watch logged about 3 miles but there were plenty of little breaks, places to sit, and lots of shade. Alberto was incredibly knowledgeable and fun.

Sarah was incredibly accommodating at the last minute, and booking this tour was a breeze. This walking tour was extremely informative, and our group left with a whole new appreciation for Puerto Rico. At just under $50 USD, it’s slightly more expensive than some other walking tours, but absolutely worth it—especially since it includes 10 different sites. The tour runs about two hours, and our guide, Pablo, made excellent use of our time. He was knowledgeable, engaging, and thoughtful throughout the experience. The terrain can be uneven at times, so be sure to wear comfortable shoes and dress for warm weather—it can get quite hot. That said, there are shaded areas along the route, and Pablo did his best to keep us out of direct sunlight whenever possible. I recommend bringing water, although there is a stop along the way for the restroom and refreshments. If this is your first time in Puerto Rico, this tour is a must. If you can, request Pablo—he truly made our experience exceptional. We’re already looking forward to booking more excursions with this company on our next trip to PR!

Carola was an excellent guide. We learned a lot of history about the land and the people. Lots of great picturesque spots were on the tour. The amount of walking and pace were very reasonable for a hot day.

Two things make this an amazing experience: first, old San Juan is a beautiful place with a rich history and second, Claudia is so knowledgeable, fun and engaging! If you like to get a feel for a place, to understand a bit of its history and how that has made it what it is today, this is a perfect tour. Thank you, Claudia!

Excellent tour of old San Juan

Alberto, our tour guide, made our tour of historic San Juan very interesting and fun. We liked the fact that the group was a small one, so we had no trouble hearing him. He was very open to questions and guided us on how to get to our parking garage when we had to depart early for our flight.

Jesus was enthusiastic, engaging, well prepared and knowledgeable. Lots of history new and old in San Juan. Good explanation of the elongated PR Christmas (lol). Might I recommend a stop for a refreshment mid way…can get a bit hot for us non-locals. Or provide water at the start. It adds a really nice touch. Great tour…worth it

This tour is a great way to familiarize yourself with the city and learn many interesting facts!!!!!

Diego did a very good job leading out your , a very good experience!

Walking around old town . Bring water as it gets hot . Wear comfortable shoes. Andreas was great. Very engaging .

Our guide Claudia was warm and informative. Make sure you wear comfortable shoes and allow time for traffic.

Amazing - Raiza was the best tour guide

Pablo was our tour guide. He was excellent. We learned so much about Old San Juan, Puerto Rico, Puerto Rican history, the various architecture styles of buildings in old San Juan, etc. I highly recommend this tour!

The tour was a nice overview of the city. I would recommend a tour to anybody visiting the city. This one met our needs.

Claudia did such an amazing job! We had some of the best food we’ve had during our honeymoon in PR, and it was fun to learn about the different history behind both the food and the restaurants we visited in Old San Juan. Claudia was a wonderful guide, super funny, and always made sure everyone was with the group and that we were having a good time! We did a three hour walking tour with a group of 10, and it was the perfect afternoon.

You’ll have more time stopping for bathroom breaks and food breaks then learning about old San Juan. Tour guide good at knowing people’s names and the individuals but that is not what we paid for. Otherwise she was knowledgeable

The tour walked us through old San Juan where we heard about the history, the architecture and importance of Puerto Rico.

This walking tour was a highlight of our trip! It was exactly as described and gave us a great understanding of the layout of Old San Juan while bringing the architecture and history to life. Leslie was fantastic — warm, engaging, and genuinely funny, which made the experience even more memorable. Highly recommend for anyone visiting!

We thought it would include El Morrow although it did not. Overall, our Guide was very fluent in English and very knowledgeable.