Old San Juan Walks; 2 Castles, El Morro and San Cristobal
Overview
Available languages
2 hours 30 minutes
Mobile ticket
UNCLE J WALKS, presents the ONLY walking tour in the old city that offers ENTRY to both iconic Castles, CASTILLO SAN FELIPE DEL MORRO and CASTILLO SAN CRISTOBAL.
Very few operators offer a Castle tour in the city, none offer two, that is, until now.
In a fun, intimate setting, let Uncle j, dressed as an 18th century soldier,
guide you through the history of the fortifications, which King Phillip 11
called “the key to the Indies’
We encourage small groups so you have ample time to take fantastic photos and to soak in the views.
A vacation highlight!
This is literally two tours for the low price of one.
Please bring water, rubber shoes and a hat. Hydrate!
Let’s create some memories!
See you soon.
PS; Tour DOES NOT INCLUDES ($10.00)entry fee to BOTH castles. To be paid onsite in cash or Venmo to guide.
Additional Info
Service animals allowed
Not recommended for travelers with spinal injuries
Not recommended for pregnant travelers
Not recommended for travelers with poor cardiovascular health
Travelers should have at least a moderate level of physical fitness
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
Castillo De San Cristobal
Castillo San Cristobal is our first stop. A UNESCO ‘National Historic Site’, has being called an ‘engineering masterpiece’ Built to repel attackers from the land. Cristobal was considered state of the art for its time. we will be here 45 minutes
Castillo De San Cristobal
Our Certified Historical Interpreter, dressed in a White Spanish Colonial uniform, will meet your party next to Christopher Columbus Statue, in Plaza Colon. Here, discovery of the island and an introduction to the local indigenous inhabitants, the Tainos wil be discussed
What‘s Included
In-person Guide: English
Entrance fee to Castillo San Cristobal and and El Morro Castle to be paid directly on site.
Options
El Morro/San Cristobal tour
Reviews
140 reviews
Total reviews and rating from Viator & Tripadvisor
Super fun old San Juan walking tour with Uncle J Walks
matthewlZ5791JS,Mar 30, 2026
- Review from Tripadvisor
5.00An absolute blast! Uncle J provides cool local historical perspectives in a playful journey back in time from fort to fort. We couldn’t have been more entertained and fascinated with our lovely tour. It was great fun for all our ages (10, 13, 16). Don’t miss this one!
uncle j the best
Alizaay A,Mar 29, 2026
- Review from Viator
5.00It was a great experience, uncle j is super nice and informative thank you so much for everything !!
Highly recommended tour of forts and a historic background of the forts and Puerto Rico.
Dean H,Mar 28, 2026
- Review from Tripadvisor
5.00Absolutely great tour! Kept us all truly interested the whole time. Right pace to allow for some rest between walking up and down some decent grades. Tons of information even though I had visited the forts previously. Great background on the socio-political environment that lead to the forts and the conflicts in which they played a role. Great guide!
Wonderful Day with Uncle J!
Brandon B,Mar 28, 2026
- Review from Viator
5.00Uncle J handled our group of 5 kids (4 to 8 y/o) and 9 adults with ease! He is exceptionally knowledgeable about the history of the island and the castillos, and he did a wonderful job keeping the kids engaged. I don't think there's a better/more efficient way to experience the history of the castillos than with a walk with Uncle J. I'm not sure if this is always the case, but the added benefit of skipping the lengthy admission lines at each site was a nice perk as well. Thanks Uncle J!
Very fun tour. The guide...
Charles G,Mar 26, 2026
- Review from Viator
5.00Very fun tour. The guide was great. Lots of knowledge, anecdotes, and nice guy. Also, his costume is awesome.
The Highlight of Our Puerto Rico Trip!
Kristin G,Mar 26, 2026
- Review from Viator
5.00We had the absolute BEST experience with Uncle J as our tour guide at Castillo San Felipe del Morro and Castillo San Cristóbal! From the moment we started, he brought the history to life in a way that was both incredibly informative and genuinely entertaining. Uncle J has a gift for storytelling—you can tell he truly knows his stuff, but what makes him stand out is how he delivers it. He mixed fascinating historical details with humor and real, down-to-earth energy that kept everyone engaged the entire time. It never felt like a lecture… more like exploring with a really knowledgeable friend who just happens to know all the best stories. He answered every question, made sure everyone felt included, and even added little personal touches that made the experience feel special and memorable. You walk away not only learning a ton, but actually remembering it—which says everything. If you’re visiting these forts, do yourself a favor and book a tour with Uncle J. It will 100% elevate your experience and be one of the highlights of your trip! Ps- Uncle J… I pray you make it to St Augustine one day!!
THIS IS A MUST DO EXPERIENCE!!!
Journey40311596266,Mar 23, 2026
- Review from Tripadvisor
5.00This was the only event I booked prior to arrival. As soon as I saw his picture I knew he was the guide for us. His consistent positive reviews over the years, confirmed we’d made the right choice. We thoroughly enjoyed our walking tour with Uncle Jay! His energy and personality created a fantastic vibe as we toured the castles. Tio was knowledgeable and provided a thorough history of the people and culture of Puerto Rico! I would give more stars if they let me!! Treat yourself and book this ASAP!
We had a great time with our small group. It was a very rainy day but Jay made the best of it. He's a great historian and he mad
Churchmonkey,Mar 23, 2026
- Review from Tripadvisor
5.00Great time even in the rain!!!
Great tour; visiting both fortresses was awesome!
Roam22756395432,Mar 23, 2026
- Review from Tripadvisor
5.00Very knowledgeable and fun guide, but just a little too soft-spoken as he was hard to hear at times, especially in open areas. Visiting both fortresses was a great experience.
Uncle J is Extraordinary
Donald B,Mar 22, 2026
- Review from Viator
5.00There is a lot of walking, at times on steep inclines and stairs. The description states this and you have to be able to make tough climbs and long walks. Uncle J is a proud Puerto Rican who will share his heritage with you. He is knowledgeable of what happened on the grounds, but more importantly he knows the ‘why’. His understanding of the global political environment over many centuries is astonishing. You will learn a lot about the strategic importance of the castles and the port. Be ready to walk on steep inclines and learn why the Puerto Ricans are a proud people.
From US$39.00
Want a private experience? Upgrade to a private tour
Related Experiences
Operated by Uncle J Walks