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
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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
Options
Historical San Juan Bay Sunset Sailing Tour
Reviews
754 reviews
Total reviews and rating from Viator & Tripadvisor
Highly Recommend
Happiness17244030459,Mar 10, 2026
- Review from Tripadvisor
5.00Capitan Ivan was capable and friendly. He shares his considerable knowledge of all things Puerto Rican with charm. Highly recommend 👍
The Captain/ Owner was...
Anthony L,Mar 10, 2026
- Review from Viator
5.00The Captain/ Owner was outstanding. He was a great host on his “ J “ boat. Fantastic views of San Juan Bay and Old San Juan. He got some great photos of my wife and I! Highly recommended this experience.
Such a great experience!
Cindy Z,Mar 9, 2026
- Review from Viator
5.00My mom and I went on a sunset sail with Captain Ivan and had such a great time! Can’t beat being out on the water in a sailboat watching the sun go down with the salty wind on your face. Captain Ivan shared interesting history and recommendations with us. I will definitely do this again when I’m in Puerto Rico next time!
Best Activity in the City
asheling,Mar 8, 2026
- Review from Tripadvisor
5.00Best thing I've done in San Juan! Captain Ivan was amazing! Highly recommend!
A must.
Ella H,Mar 4, 2026
- Review from Viator
5.00Captain Joe was amazing, this whole experience is awesome. Joe feels more like a friend than a your guide, he’s incredibly knowledgeable. His wife and co captain Maria is amazing as well. 10/10 cant recommend enough.
The boat ride was great...
Loutisha G,Feb 28, 2026
- Review from Viator
5.00The boat ride was great from beginning to end! We were greeted at the entrance of the Marina which eliminated any confusion on where to go. Both gentlemen were inviting, polite and informative. The sangria was tasty and the captain (I think that’s the correct terminology) was very interactive with the patrons. I 100% recommend this activity while visiting Puerto Rico!
Very relaxing. You get a...
Peggy M,Feb 27, 2026
- Review from Viator
5.00Very relaxing. You get a history of old San Juan and beautiful views and the sunset was breathtaking. The crew was great
Time of Our Lives!!!
Trail35099302853,Feb 26, 2026
- Review from Tripadvisor
5.00We had a great experience!!! Captain Joe & his first mate Edgar were very easy to get comfortable with. They made you feel safe and comfortable! They pointed out historic buildings and had some stories to tell. We really enjoyed them and their easy camaraderie. The weather was cloudy but beautiful. There wasn’t really a sunset because of the clouds, but there was a clear view of the moon! The real highlight was seeing DOLPHINS!?! They recommended some good places to eat, too. We would definitely do this again.
Didn't make boat for reasons beyond our control
J7019VEkurtw,Feb 21, 2026
- Review from Tripadvisor
1.00Never showed up to meeting spot or they gave the wrong meeting spot. Either way terrible customer service and no response from either Trip Advisor. I would avoid this one.
Relaxing tour of the water way, calming.
Chris K,Feb 18, 2026
- Review from Viator
5.00Ours was a smaller sail boat which made the experience cozy. We really liked it. Our pictures are really clear and nice.
From US$119.00
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Operated by Sail San Juan Bay