Old San Juan 2 Castles Walking Tour: El Morro & San Cristobal

If you’re looking for a small group history tour, this is the one! Uncle J was fun, quirky, and was well loved by the locals. We saw so much and learned a lot in just over two hours.

Great tour! A great balance of knowledge and humor. It’s clear that Uncle J knows a lot about the island. He showed up in full costume like the picture - that’s dedication in the hot weather. Be prepared to walk a lot so bring lots of water and stay hydrated.

Uncle J was funny, knowledgeable and entertaining. So helpful to have a guide to the behind the scenes on our tour (even getting us in without waiting in line). The information and history added so much to the depth of our time and understanding of PR.

I certainly enjoyed the one on one walking tour of both castles. Captain J was both fun and very informative. I thought the costume was an excellent touch. Captain J made sure to keep me hydrated in the heat of the day. Would love to do it again. Thanks Captain J.

Uncle J is really fun! He knows a lot about the history of the castles and showed a lot of great views of the area. I would recommend the tour to my friends.

Uncle J is the absolute best and this tour was a highlight of our time in San Juan! Not only does this tour include two Castles and a scenic walk, but Uncle J brings it all to life with his incredible knowledge and sense of humor. Walking around with Uncle J we noticed that he is clearly loved by the community and he was greeted with enthusiasm everywhere we went! That sense of connection made us feel like we were in very good hands, guided by someone who knows the history, the people, and the community inside and out. Highly recommend this tour to anyone coming to Puerto Rico!

One of the best experiences you will have bar none. Uncle J is amazing and is passionate about his history.

Tonton J. Beaux garçon. Was very detailed oriented about the castles my husband and I had a great time, we would do it again best tour ever. This is from your Haitian brother and wife Charles and Anna. You were very entertaining and knowledgeable also very flexible. We had a great time together you made our vacation spectacular. Thank you 🙏🏾 please keep the momentum going. God bless .

Had a wonderful time with Tío J. Full of historical knowledge, funny and caring. I would 100000% recommend this tour with Tío J.

We thoroughly enjoyed our tour of El Morro and San Cristóbal with Uncle J! His knowledge of Puerto Rican history is remarkable, but what really makes his tour special is the enthusiasm and genuine love he has for what he does. He brings history to life in a way that’s both interesting and entertaining. One thing that particularly impressed us was how well-known and warmly welcomed he seemed to be everywhere we went. He clearly has wonderful relationships with the people in his community, which made the experience feel more personal and authentic than a typical guided tour.

Uncle J is a wealth of knowledge and made the experience unforgettable. Fantastic guide where you learn more than you could just walking through.

Great tour! Wonderful communication, easy meeting spot. Very informative. My parents and kids loved it :-)

Uncle J is very knowledgeable and gives history from all perspectives. Amazing value for this experience. If you enjoy history or just want a little more insight about the island this is a must try.

Uncle J was absolutely fantastic! He was knowledgeable, friendly, funny, and made our tour of Old San Juan unforgettable. He’s truly a walking encyclopedia of Puerto Rican history, but somehow makes every story fun and engaging. We learned a lot, laughed a lot, and had an amazing time. If you want a tour guide who treats you like family, Uncle J is your guy! Highly recommended! 🇵🇷👏😄

⭐⭐⭐⭐⭐ 5/5 – Highly Recommended! Uncle J was an amazing tour guide! 🇵🇷 He’s truly a walking encyclopedia of Old San Juan—knowledgeable, funny, friendly, and full of great stories. He made the history of the city and its forts come alive while keeping us entertained the entire time. We learned a lot, laughed a lot, and had an unforgettable experience. If you’re visiting Old San Juan, definitely take a tour with Uncle J—you won’t regret it! 🙌🇵🇷

Uncle J was a great guide and very knowledgeable, definitely recommend.

Fantastic tour. Uncle J brought a wealth of knowledge, understanding the history really made the castles come alive. Learning about the colonial history, the naval battles, political struggles, and military strategy of the castles was incredibly cool. Super funny and fun interpersonally too- a genuine character who knows San Juan inside and out. Just a good hang for a couple of hours who can help you get an inside scoop on the island. As a tour itself, well planned with good pace. A walking tour as advertised but with rest stops and water breaks to in cool locations where we’d learn about certain areas of the fort. A good strategy given the heat that day. 10/10 would recommend! If you want insider recs, love history, or just want to take in some breathtaking sites then this is for you.

We had an amazing time with Uncle J! He is truly one of Old San Juan’s most colorful characters. His knowledge of El Morro, San Cristóbal, and the rich history of Old San Juan was incredible. He brought the history to life with fascinating stories, humor, and a personality you won’t soon forget. We learned so much while having a great time along the way. If you’re looking for a tour that is both informative and entertaining, Uncle J is your guy. This was definitely one of the highlights of our trip to Puerto Rico!

Uncle J was amazing! He was patient with my younger sons, went at our pace, and was very knowledgeable about the history of the castles. This was our favorite tour of the trip! Thanks for a great time in San Juan!

Today's tour with Uncle J was a great experience. His passion for history and people is evident. He took us to the many and great views of castille san cristobal and el morro. And every step of the way he taught us its story. Me and my boyfriend learned a lot and can now identify dry moats easily lol. We also appreciated his restaurant recommendation too :). You wont regret choosing this tour. Remember to wear bug spray (i got 5 mosquito bites) and its better to wear sneakers because there were some unavoidable puddles that I felt in my flip flops.

Our tour with Uncle J was excellent! The evening before the tour we received a courtesy text from Uncle J confirming the tour time and meet up spot, we replied to the text confirming we would be there and he was very responsive. It was nice to know we could contact him directly if we had any issues. When we first met in person the morning of the tour, he greeted us with a friendly conversation and his awesome attire. We talked about his background as well as ours, and he prepped us for his plan for the tour. Before we started walking he gave us a brief historical background on the Spanish colonization to the new world and the design and building of each castle. By the time we had arrived at the first castle we felt as though Uncle J was an old friend and we were going to enjoy the tour. Uncle J seemed to know and have a good relationship with the Park Rangers in both castles. He brought us inside both castles, took care of registration and admission into the castles and we loved not having to worry about any of that. He shared lots of great historical information as we toured the open areas, tunnels, and sentry boxes of each castle and he made sure that we got to see and get photos of all of the amazing views. It was a lot of fun to see him interact very briefly with others as they saw him walking by. He was more than willing to listen to comments or answer questions we had along the way. We definitely had the best time and received outstanding treatment! This is very possibly the best tour experience we've ever had at any vacation/historical spot.

You won’t find a better tour on the island. Whether you are two people or ten people, Uncle J is INCREDIBLE. His historical knowledge and knowledge of the island is engaging and fun and has amazing depth. The 2.5 hours flew by- between breath taking views, rich history, and the wit of Uncle J, you couldn’t spend your time any better way. You get your money’s worth and more, so look no further than Uncle J!

We had an amazing time touring two castles in Puerto Rico with Uncle J as our guide! From start to finish, he made us feel completely comfortable and at ease. His warmth and sense of humor turned what could have been a standard tour into a genuinely fun and memorable experience. We were laughing just as much as we were learning. Uncle J clearly knows the history and stories behind both castles, and he shared it all in a way that was easy to follow and engaging for everyone in our group. It's obvious he loves what he does, and that passion made the whole tour better. If you're visiting Puerto Rico and want a guide who's knowledgeable, friendly, and fun to be around, book with Uncle J. Highly recommend!

Uncle J is the best! Go with him! The others don't even compare. He was kind, generous with his time, thoughtful of our special needs and extremely knowledgeable. You know how great a guide is when all of National Park Service workers and shop owners stop him along the way to say hi and greet him and give him high 5's. His pirate looking outfit is amazing and his English was perfect (he speaks fluent Spanish as well). Plus, he tours both castles, which most of the other guides don't! I would highly recommend him!

Uncle J was super was super knowledgeable and had tons of historical facts to tell us. It was also super cool to be walking around El Morro with a soldier and we got some great pics!

A lot of walking so make sure you wear comfortable shoes and stay hydrated. My Husband and I learned a lot about the castles and what the island have been through over the past years. Taking a tour with Uncle Jwalk worth it because he knows so much about the castles and history.

Uncle J was great! Loved his costume. Many facts and great history. The tour of both of the forts was remarkable. Uncle J was very knowledgeable and informative. He made the tour fun and interesting. A patient and funny guy. I highly recommend his tour, he's the best 👌

Best walking tour! Uncle J was great, and this tour was the perfect mix of guided history and solo exploration. It was hot (we did the 2pm tour) but the crosswinds helped keep us cool and Uncle J made sure everyone was OK. We had a great time. Be prepared to walk (there are breaks for water and the bathroom) and bring water.

What a great tour! We spent our first afternoon in San Juan with Uncle J on the castles tour. Very interesting and informative and a great way to start our vacation in PR. Uncle J has a great personality and really knows the history of the castles. My 15 year old grandson really enjoyed it as did I. I would highly recommend Uncle J castles tour to anyone wishing to gain insight into the history of the island.

First and foremost- best tour I have ever taken, and here's why: Uncle J takes a different approach to most mundane tour guides in that he mixes his deep PR historical knowledge with a conversational style that brings history to life and makes it more comfortable to engage and ask questions. Also loved his Pirate/Soldier costume! As we toured San Juan, Uncle J was treated like a Rock Star by locals and tourists alike. He graciously posed for pictures with kids upon request and without disrupting the tour. 5 STARS and will recommend without hesitation!

Amazing Tour and Guide! I was seeking a unique experience. Not the same dull tours I have taken in the past. I love history, but it’s more impactful when delivered in a fun, conversational, relatable way. Uncle J is an absolute ROCKSTAR around Old San Juan dressed in 1500’s soldier/pirate garb. Kids and parents alike clamored for pics with him and he handled them graciously without missing a beat in the tour. Watching him work was a big part of the fun. That aside, Uncle J is a legit native of PR with a deep knowledge of its history. He also does not sanitize or rewrite history. He calls it as it was warts and all. I appreciated his unvarnished integrity. All in all I can’t say enough and have told my fam and friends. Uncle J Walks tour know k it out of the park!

Lots of good historical information . Our guide was engaging,, knowledgeable, and personable. However, once we saw one fort, we weren’t up to seeing the second. It sounded as though it was gonna be basically more of the same. We thanked our guide and left happy with our tour! Lots of walking Wear comfortable shoes Bring water and wear sunscreen

Uncle J was great. He was very informative and engaging. My boyfriend loved the experience wants to do it again.

Uncle J was prompt, knowledgeable, and professional. Despite it just being the two of us, he didn’t cancel on us (which was much appreciated). Most tours will cancel if a minimum hasn’t been met. Grateful he honored our booking. Took lots of pictures for us and educated us on the history of both castles in a fun and memorable way. Though we’d imagine the pirate costume would be hot to be dressed up in, he not only manages but is very responsive to kids and adults alike that are thrilled to see him as a pirate. Definitely, recommend.

Uncle J is AMAZING! Such a knowledgeable, kind, and funny guy! 10/10 experience, highly recommend!!! LOVE UNCLE J!!!

Uncle J was great! Kind, knowledgeable, funny, and enjoyable to be around. What else would you want from a tour guide?!

Really enjoyed all that we learned with uncle J about the history of Puerto Rico. He is very passionate about it. Definitely worth it if you wanna learn about the history of the Puerto Rican people and the forts.

My daughter and I had a great time. Uncle J was very knowledgeable. He made fun learning about history.

Uncle J was AWESOME! When the tour started it was just my husband and I (the others were delayed) so we got to ask tons of questions and Uncle J had all the answers! I learned a ton of stuff that my husband evidently already knew. Being able to talk to Uncle J about all the 'unknown' facts made my husbands day. After the tour officially ended, Uncle J walked us back to our starting point and went over several more interesting sights in San Juan, even recommending a few restaurants for us to end our day. If you are looking for a great, fun and knowledgeable tour, this is it. We will take it again next time we are there. I gave 5 stars because 100 was not an option!

Some choose to wander the castles , but a guided tour greatly outweighs wandering aimlessly, the historical facts that uncle jay provides while touring both castles takes you back to a time where pirates & life & sea were the norm.

Uncle J was the best. Loved the tour. Rode the bus with the guy. Yo uncle j. Its jeff , 9393827317

Uncle J gave us one of the most memorable days of our entire trip. He took us on a walking tour of the two iconic forts in Old San Juan — Castillo San Felipe del Morro and Castillo San Cristóbal — and brought them to life with a depth of knowledge that only someone who truly loves this island could share. He didn’t just explain the history; he told the story of these places — their purpose, their battles, their role in shaping Puerto Rico. Every stop came with rich context, fascinating details, and that extra bit of flavor that made us feel like we were seeing the forts through the eyes of someone who grew up with them. Beyond being an incredible guide, Uncle J is simply a good soul. Warm, patient, funny, and genuinely invested in making sure everyone has a great time. You can feel his pride in the island and its history, and it’s contagious. It was a wonderful day — the kind you remember long after the trip is over. If you’re visiting Old San Juan, do yourself a favor and book a tour with Uncle J. You’ll walk away with new knowledge, great memories, and a deeper appreciation for Puerto Rico.

Had a wonderful time with Uncle J. He was knowledgeable and kept the tour very interesting. Would recommend to any that is visiting the island.

Uncle J was great, charisma & very knowledgeable & very fun. He made this experience very fun and very enjoyable!!

We had an amazing tour with Uncle J visiting El Morro and San Cristóbal! He was incredibly knowledgeable, friendly, and passionate about Puerto Rican history. He made the experience both educational and fun, sharing interesting stories and details that brought the forts to life. Uncle J was patient, engaging, and made sure everyone felt welcome throughout the tour. You can tell he genuinely loves what he does and takes pride in showing visitors the beauty and history of Puerto Rico. If you’re looking for a great guide to explore Old San Juan and its historic landmarks, I highly recommend Uncle J. Thank you for helping make our trip so memorable!

Very informative which was nice. Had the pleasure of having a solo tour with the man himself. I’ll definitely be booking another tour with Uncle J to retain all the history he was teaching me.

Uncle J was funny & knowledgeable & we learned many fun facts as well as saw many amazing views. It put the whole of Old San Juan into perspective. It was a very enjoyable & unique way to tour the most important historical parts of Old San Juan.

Uncle J was personable, knowledgeable, and made the journey worthwhile, even for our 9 year old who struggled with physically navigating the terrain (lots of walking with steep inclines and declines). The history lessons we walked away with and the appreciation for the cultural experience that is Puerto Rico is a direct result of our time with Uncle J. The castles were marvels to witness, but the depth of knowledge and history offered extended well beyond the castles. Uncle J even extended his time with us walking through Old San Juan to make recommendations for eateries and other things to experience after the tour. We would recommend this experience to anyone with a penchant for exploration and appreciation for the stories of Puerto Rico!

Our guide, Uncle J, contacted us the day before the tour with helpful information and directions, which made everything very easy and organized. The biggest advantage of this tour was being able to visit both El Morro and San Cristóbal in the same day without having to coordinate everything ourselves. Uncle J did a great job explaining the history, architecture, and strategic importance of both forts, and kept the tour engaging and enjoyable throughout. The views were beautiful, there was plenty of time for photos and questions, and the pacing felt very comfortable. I would definitely recommend this tour to anyone wanting to experience both historic sites in one visit.