Expiring Soon
This date becomes unavailable for instant booking in less than 1 day.
By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.
This date becomes unavailable for instant booking in less than 1 day.
Experience the thrill of our 3 hour excursion, private, only for you! From one to 6 people, this package offers exceptional value, 3 hours of adventure on the water. Discover the beauty of Old San Juan from a unique perspective and create unforgettable memories with your group. Book now to secure your spot on this remarkable journey! Set sail for 3 hours of exploration, soaking in the rich history and breathtaking views of Old San Juan. Choose between morning (10 AM - 1 PM) or afternoon (2 PM - 5 PM) departures to suit your schedule and preferences. Experience the beauty and history of Old San Juan like never before—reserve your private cruising sailboat adventure today!


This is the best sailing charter ever! The day was made for sailing, and we enjoyed every minute of it. This is exactly what we wanted. Thank you!!
BC
Our group was raving about this experience for so long after left! What an amazing time and Jimbo made the experience what it was! Educational, fun, relaxing, and exciting all in this 3 hour trip. Couldn’t have been better
SK
If you are looking for an authentic sailing experience in Puerto Rico, look no further. This is for you! We came in with sailing experience but not in the ocean and not on as large of a boat. He let us sail the entire time and taught us along the way. Jimbo is a very experienced sailor and is looking to give you the sailing experience you are looking for. If I could have given him more than 5 stars I would have!
FS
This experience was amazing! This was the first time my family experienced a sunset ride on a sailboat and Jimbo made sure the experience was one we'd always remember. Jimbo ensured we were in the know on all safety protocols and during the sail, enlightened us with facts and history about Puerto Rico. Jimbo was personable and accommodating from the beginning to end of our excursion. This was our first, but not our last trip with Jimbo!

This was my first time on a sailboat. I learned that I am afraid of sailboats ⛵️ But if you are comfortable on them you will enjoy yourself tremendously. Jimbo is the perfect Captin. If you have kids he will let them drive the boat.

We are located between San Juan and Fajardo, Puerto Rico.
You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
Free cancellation up to 2 days before your trip.
Frequently Asked Questions: • Are children allowed? Yes. All ages. Everyone is counted as a passenger, even if they are carried on a lap. • Where do we go? What do we see? We Sail from our dock out into the San Juan Bay, aiming at the old historic Spanish Forts. We will talk a little history if you like, and have a cocktail or two. The Captain can usually let you sail, if that’s what you have in mind. • What if it rains? - Trips will continue during light rain or passing storm. If the safety of the vessel is in question, the Captain has the right to abort/cancel. • Wheelchairs? - Most boats are not wheelchair accessible. However, if a guest feels confident enough to take our boat trips then we can be accommodating. • Do you serve food? We do not include food but, you are welcome to bring your own. Light alcoholic drink, Sodas and water are included. Price is for the Whole Boat, Private.