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.
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.
Reviews collected by Viator and Tripadvisor
For a full refund, cancel at least 24 hours before the scheduled departure time.
Historical San Juan Bay Sunset Sailing Tour lasts about 2 hours. The itinerary has 1 stop.
Prices start at $119 per person for this San Juan experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
The meeting point is SEARCH FOR:. SAN JUAN BAY MARINA in your online maps. WAIT BY THE GREEN PEDESTRIAN GATE STAFF WILL PICK YOU UP. We won't be able to take phone calls or chat. Hotel pickup is not part of this experience.
The experience is available in EN.
It is a small-group experience with a maximum of 6 participants.
Infants are required to sit on an adult’s lap
Confirmation is sent by the operator within 24 hours of booking.
Travellers rate it 4.5 out of 5 across 783 reviews on Viator and Tripadvisor; it is run by Sail San Juan Bay.
Reviews collected by Viator and Tripadvisor
Wonderful experience on this sunset sailing trip. The captain was very personable and extremely knowledgeable about the history of Puerto Rico. Drinks were included and delicious. A relaxing and low key vibe. Just a really fun and amazing sailing experience. Would definitely do it again next time we are on the island.
What an amazing excursion!!! Ivan was so pleasant and informative. Ivan was so kind! Will book again.
Best experience ever! Nice trip with a small group of people. Our captain ‘Ivan’ is very awesome, well knowledgeable about Puerto Rican history, good sailing, great vibes and just fun all around. Highly recommend to this amazing activity :)
He was so knowledgeable about the area. It was an amazing sunset sailing ride with a history lesson. We loved it.
Such a pleasant ride on the water at sunset. I truly enjoyed the information provided and captain. The sangria didn't hurt either. :-)
This is a low key sail around the bay with a local sailor. I really enjoyed it, but it is not a party cruise!
Capt. Ivan is a hoot and quite entertaining. He truly loves sailing and Puerto Rico. He lets you guide the sailboat which was fun. As a family, we enjoyed this but it’s a little more rustic than we expected. If you want a luxury sunset cruise, go on a catamaran. Having said that, it was a great small boat sailing experience. Seeing the mega yachts in the marina was unbelievable. The capt was more than willing to share restaurant recommendations and guided tour suggestions.
Wonderful experience with Captain Joe!! Fun tour on his sailboat in the harbor. Sadly, the clouds did not cooperate with the sunset plans, but that was not his fault. We shared laughs and stories and Captain Joe shared some interesting history. 100% recommend!!
Best time! My son was able.to steer the boat and we all had the best time! Definitely recommend!!! Must try
We had an amazing time on the trip. The staff was thoughtful and you can tell they were very experienced. The boat was clean and comfortable, perfect for a group of 4. We had an excellent time on the cruise, our guide Ivan was an expert sailor and also gave us plenty of explanations of what we were seeing along the way, as well as suggestions on authentic experiences within Puerto Rico! Would highly recommend to anyone looking for a sailing experience around San Juan.
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Historical San Juan Bay Sunset Sailing Tour | 2 hours | 4.5 (783) | $119 | |
 San Juan Sunset Harbor Boat Ride | 1h 30min | 4.6 (1,478) | $99 | View |
 Puerto Rico Sunset Magic: Bio Bay Kayaking Tour from Fajardo | 2 hours | 4.8 (244) | $69 | View |
 Bio Bay Night Kayaking with Transport from San Juan | 2 hours | 4.1 (30) | $125 | View |
 Full-Day Zipline and Waterfall Rappelling Adventure Near San Juan | 6–8 hours | 5.0 (963) | $165 | View |
 Janise Sailing Afternoon Charter in Fajardo, Puerto Rico | 3 hours | 4.9 (22) | $229 | View |
 Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico | 5 hours | 4.9 (175) | $299 | View |