Historical San Juan Bay Sunset Sailing Tour
Overview
Available languages
2 hours
Mobile ticket
Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no crowds, no fake pirates, no crowds, no need to scream. We sail aboard a real racer cruiser (J30), with a toilet and a cabin- just real life sailing. You'll get to see a different perspective of old San Juan, with complimentary drinks, feeling safe but free, in parties up to 6 people. This is great for a special moment, or turning this moment into an special one. While in contact with nature, you may spot a dolphin. This is not a luxury yacht or a catamaran, so it's possible to really connect with the nature around you.
Additional Info
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Not recommended for travelers with spinal injuries
Not recommended for pregnant travelers
Not recommended for travelers with poor cardiovascular health
Suitable for all physical fitness levels
no heels, or hard soles
SAN JUAN BAY MARINA is in Google Maps and Waze.
We will cancel if weather is rough or rainy. You'll get refunded.
Maximum passenger weight 275
We reserve the right of admission
WE WILL PICK UP AT SAN JUAN BAY MARINA PEDESTRIAN GATE
We don't accept phone calls
Show up at least 15 minutes earlier, we depart ** SHARP **
BAd reviews come from individuals who never sailed with us, because didn't showed up BEFORE departure time or didn't read our recommendations here, that for manny of us are obvious
Maximum weight 275
What To Expect
San Juan Bay
Experience the perfect blend of history, serenity, and adventure with our San Juan Sunset Sailing Tour. Board our racer-cruiser sailboat and glide through the calm, flat waters of San Juan Bay. Sail close to the iconic Castillo San Felipe del Morro, where you can capture stunning photos against this majestic fortress. Marvel at the lively commercial activity of the harbor while enjoying the breeze and panoramic views. As the sun sets, relax and take in the breathtaking scenery, making this two-hour sail an unforgettable way to see San Juan. Whether you're a seasoned sailor or a first-time adventurer, our tour offers an exhilarating and memorable escape on the water. Join us for a truly unique sunset experience that highlights the best of Puerto Rico.
What‘s Included
Non-Alcoholic Beverages
Light refreshments
Bottled water
All taxes, fees and handling charges
Beers, Sangria and Rum n Coke
Local operator does not accept calls or texts, please read all information thoroughly
Transportation to the Location
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Options
Historical San Juan Bay Sunset Sailing Tour
Reviews
770 reviews
Total reviews and rating from Viator & Tripadvisor
Must-Do Activity
Caleb B,May 26, 2026
- Review from Viator
5.00A great way to see Old San Juan and learn about the history and culture of the area. A smooth ride and small group makes this experience really enjoyable.
A very personal...
Angela S,May 12, 2026
- Review from Viator
5.00A very personal experience with engaging, heartfelt conversation! Not to mention, a fun and different view of San Juan from the water.
Not thier fault, we...
RaShad P,May 3, 2026
- Review from Viator
1.00Not thier fault, we missed the booking because of another booking and traffic, if you're doing this booking only do this one or you'll lose money, other outing take a long time driving around
Perfect!
John R,May 2, 2026
- Review from Viator
5.00Amazing experience! The captain is fantastic. Friendly, fun, knowledgeable, makes you feel safe. Follow the provided instructions and you won't have a problem. Put "San Juan Bay Marina" in your uber app/gps. Meet at the green gate, next to the building. Arrive a few minutes early because the boat leaves at the scheduled time. It's not a party boat (in the best way). Highly recommend and would absolutely book this tour again.
If I could give 6 stars I would!
Molly B,May 1, 2026
- Review from Viator
5.00Ivan was a fantastic guide - it was easy to meet up with him and get on the boat. We got to help steer, enjoyed some drinks, and had plenty of photo ops. Ivan also gave us plenty of food recommendations. We had a great experience with him and the other couple on board - highly recommend! I would be sure to wear comfortable shoes and have your cameras ready :)
Lovely evening sail around the harbor
Naomi G,Apr 23, 2026
- Review from Viator
5.00We had an amazing time with this experience. Captain Ivan was friendly, and kind, and very hospitable. We all had a really lovely evening. His knowledge about San Juan and Puerto Rico (history, current events, and local culture/restaurants) kept us well entertained as it was all very interesting. The views were beautiful, and it was the perfect amount of people. My daughter was thrilled to have a chance to turn the rudder as we came back in.
Total rip. Stole $230.00 from me for nothing.
BARRY H,Apr 21, 2026
- Review from Viator
1.00Got to green gate a half hour early. Was never more than 10 feet away from gate. A guy came and asked if we were there for sunset tour we said yes. He looked said we weren’t on the list. Figured it was a different tour. Asked about it and discovered where they were docked and walked to the slip only to find out it was gone. We did our part. Requested refund and was denied. Got to the slip in in a couple minutes. This was a total scam and rip off. The last time I use Viator crap
Perfect
P2054EVivanp,Apr 16, 2026
- Review from Tripadvisor
5.00This sunset sailing tour ended up being one of the best decisions of our entire trip to San Juan. If you’re looking for something that feels intimate, relaxing, and genuinely memorable not just another crowded tourist activity this is it. What really sets this experience apart is how personal it feels. With only a small group on board, it’s nothing like those packed catamaran tours. It felt more like being invited out on a private sail with friends. The captain was not only skilled but also incredibly welcoming and knowledgeable, sharing just the right amount of history and local insight without ever making it feel like a lecture—something many reviewers consistently highlight. The views are the real star of the show. Watching the sun set over Old San Juan from the water gives you a completely different perspective of the city calm, beautiful, and almost surreal. The combination of ocean breeze, golden light, and the skyline is hard to beat, and it makes for amazing photos. Another standout detail: the atmosphere. Drinks are included and flow freely, but it never turns into a party boat vibe. It stays relaxed and peaceful, which makes it perfect whether you’re with a partner, friends, or even family. Many people describe it as the highlight of their trip, and it’s easy to see why. A couple of small things to keep in mind: they run on time (seriously—don’t be late), and because it’s a real sailboat, you’ll feel the motion of the water, which actually adds to the authenticity of the experience. Overall, this is one of those rare tours that actually lives up to the hype. Beautiful views, great company, and a laid-back vibe that lets you truly enjoy Puerto Rico from a unique perspective. Highly recommend booking this early in your trip, you’ll wish you could do it again.
Amazing experience!
danielbJ3206EW,Apr 15, 2026
- Review from Tripadvisor
5.00Captain Ivan is super charismatic and knowledgeable! The experience was unforgettable. Beautiful vistas of Old San Juan and the sunset made for great memories and photo opportunities. The drinks were very generous and we enjoyed every bit of it. It was very engaging and steering the sailboat was a blast. This was definitely a highlight of our visit to Puerto Rico and we strongly recommend it!
So glad I did this!
amandacS2421GL,Apr 11, 2026
- Review from Tripadvisor
5.00My 18-year-old and I did the sunset sail and it was amazing! Beautiful views, great pictures and interesting history revealed by the captain. I highly recommendthis tour!
From US$119.00
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Operated by Sail San Juan Bay