Old San Juan Walks; 2 Castles, El Morro and San Cristobal

Experience the Best of Old San Juan’s Fortifications with Uncle J

If you’re visiting San Juan and craving a deep dive into its historic fortresses, this tour might just be the highlight of your trip. For $39 per person, you get approximately two and a half hours of guided walking through the two most iconic castles: Castillo San Cristobal and Castillo San Felipe del Morro. Led by Uncle J, who dresses as an 18th-century soldier, this tour offers more than just a walk — it’s a lively, engaging journey through the city’s defensive history.

What makes this experience special is the entry to both forts included in the price. Many tours skip one or charge extra, but here, you get a full picture of why these structures are called the “key to the Indies”. Plus, Uncle J’s approach — blending humor, detailed storytelling, and a personal touch — makes history come alive in a way that sticks with you long after the tour ends.

A possible consideration is the physical demands: expect lots of walking, climbing stairs, and potentially limited shade. If you have mobility issues or prefer a more leisurely pace, this is worth bearing in mind.

This tour is ideal for history buffs, photo enthusiasts, and travelers eager to see San Juan’s biggest sights with a knowledgeable guide. If you love a personal connection and insider tips, Uncle J’s small group experience will suit you perfectly.

Key Points

• Exclusive Access: Entry to both Castillo San Cristobal and El Morro is included, saving you $10 per castle.
• Expert Guide: Uncle J adds flair with his storytelling, humor, and colonial soldier costume.
• Stunning Views: The forts offer sweeping vistas of San Juan and the Atlantic.
• Physical Activity: Prepare for considerable walking, stairs, and some ramps.
• Small Group: Intimate setting ensures personalized attention and photo opportunities.
• Value for Money: Two forts, expert narration, and memorable scenery all for $39.

A Deeper Look at the Tour Experience

Starting Point: Castillo San Cristobal

Your journey begins with Castillo San Cristobal, a UNESCO site built to defend against land attacks. Uncle J greets you next to the Christopher Columbus statue in Plaza Colón, setting a friendly tone. You’ll spend about 45 minutes exploring this massive fortress — a true engineering marvel. Clad in colonial attire, Uncle J’s stories illuminate why Cristobal was considered state of the art, with its complex labyrinth of tunnels, ramparts, and lookout points.

Visitors consistently praise the guide’s knowledge, with one reviewer remarking, “Uncle J was a wealth of information. With him being our guide, we learned a lot more about the castles.” The focus here is on understanding how these walls protected the city and their strategic importance in the broader context of Caribbean defenses.

Walking to El Morro

From San Cristobal, the walk along Calle San Sebastian to the next fortress is part of the experience — a chance to soak in the vibrant streets of old San Juan. This walk takes around 15 minutes and is a good opportunity to admire the colorful colonial buildings, boutique shops, and lively atmosphere. Uncle J’s commentary continues along the way, sharing insights about the city’s layout and history.

El Morro: A Majestic Fortress

Once at Castillo San Felipe del Morro, you’ll spend about an hour exploring this six-level fortification. Without giving away all the surprises, it’s enough to say this structure is imposing, with breathtaking views of the Atlantic Ocean. Visitors often comment on how spectacular the panoramas are and how the massive walls seem to blend history with natural beauty.

Uncle J’s storytelling here makes the fortress more than just stone and battlements. Reviewers highlight his ability to balance detailed historical facts with fun anecdotes, making the experience both educational and entertaining. “He explained everything with passion and detail,” one traveler noted.

The Overall Flow and Pacing

The tour’s structure, with strategic stops, ensures you get a comprehensive look at San Juan’s defenses without feeling rushed. The small group format allows Uncle J to tailor the experience, answer questions, and encourage plenty of photo stops. As one review states, “Uncle J kept the tour moving at a nice pace, with breaks when needed, and answered all our questions.”

Practical Considerations

Remember to bring water, wear comfortable shoes, and a hat — especially since the Puerto Rican sun can be intense. The tour does not include the $10 admission fee to each castle, payable at the entrance, but this is a small price for the access and insights you gain. Many guests also appreciated Uncle J’s pre-tour contact via WhatsApp, which made meeting up smoother.

What Travelers Are Saying

The overwhelming majority of reviews are glowing — with a 4.9 out of 5 star rating from 74 travelers — praising Uncle J’s knowledge, humor, and personal touch. Several mention how much they learned, with comments like “This tour is one we will always remember,” and “Uncle J was brilliant.”

Some highlight the physical aspect, noting the amount of walking and stairs; one reviewer aptly said, “Be ready to walk for long distances and climb stairs,” which helps future travelers prepare.

The experience delivers excellent value — combining two major sites, insider stories, and stunning vistas — making it a memorable part of any San Juan visit.

Why This Tour Is Worth Considering

If you’re someone who loves history, small-group intimacy, and vibrant storytelling, this tour will appeal. It’s especially well-suited for visitors who are comfortable with walking and climbing, as the terrain is demanding at times. Families, history enthusiasts, and solo travelers who want a thorough, fun look at San Juan’s defenses will find this experience rewarding.

The guide’s personal touch — from his colonial uniform to his humor and knowledge — elevates what could be a routine sightseeing outing into a true cultural encounter. Plus, the included access to both forts makes it a smart choice for those on a budget seeking maximum value.

FAQ

Does the tour include admission fees?
No, the $10 entrance fee for each castle is paid separately at the door. The tour includes the guide’s narration and the walk between sites.

How long does the tour last?
The tour runs approximately 2 hours and 30 minutes, including walking, exploring, and story time at each fort.

Is the tour suitable for all ages?
It’s best for those with moderate physical fitness due to walking and stairs. Small children or mobility-impaired travelers should consider this before booking.

What should I bring?
Water, comfortable shoes, a hat, and sun protection are essential. Bring a camera for the spectacular views.

Can I join if I only want to see one fort?
This tour specifically covers both castles as part of a combined experience, but you can pay the entrance fee separately if you wish to visit only one.

How do I find the guide?
Meet Uncle J next to the Christopher Columbus statue in Plaza Colón, in front of San Cristobal. He communicates via WhatsApp prior to the tour for smooth coordination.

To sum it up, this tour offers a fantastic blend of history, scenery, and storytelling. Uncle J’s engaging style, combined with the opportunity to explore two of San Juan’s most significant defenses, makes it a standout choice for travelers seeking authentic, memorable experiences. Whether you’re a history buff, a photographer, or someone simply eager to learn about Puerto Rico’s past, this walk delivers on all fronts — at a price that’s hard to beat. Just remember to wear good shoes and bring your curiosity along!