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The Best Sailboat Rentals in San Juan
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in San Juan
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$445-$1,950
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$500-$2,195
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$160-$670
Fishing Charters
Let a captain do the driving while you do the fishing
$160-$670
Kayaks
Who says you need a motor to have fun on the water?
$195
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$630
Recent Reviews in San Juan
JC
Jose
Private San Juan Bay Cruise 37' Sailboat
Captain Luis & Andrea were incredible. My group enjoyed their energy and appreciation and even though we dealt with some rain and gray sky’s, our experience was phenomenal. I would not only recommend Luis, but I would take another trip out with him when I return to PR. We had an exceptional time at sea. Gracias por todo y hasta la próxima.
Jennifer
Private San Juan Bay Cruise 37' Sailboat
Captain Luis and Andrea were fantastic. I highly recommend their charter! Thank you for a great trip!
MB
Meaghan
Private Luxury Catamaran - Old San Juan
Am absolute must when visiting Old San Juan! The boat is clean, spacious, and the crew is wonderful. This will be a regular occurence on our trips to PR now!
LB
Lauren
Private Luxury Catamaran - Old San Juan
Our bachelorette group of 7 had the best time! The boat was totally luxurious and perfect for a group party.
GS
Genevieve
Private San Juan Bay Cruise 37' Sailboat
I booked with Captain Luis for my sister’s 30th birthday trip, and we all had the best experience! There were 4 of us in San Juan for a long weekend and this was the highlight of our trip. We felt safe, welcome, and taken care of the whole ride - the captain brought refreshments including Sangria that his wife had made which we all loved. He sailed us around and anchored at a beautiful spot to jump in and swim which was so fun. I highly recommend!
SA
Samuel
Private San Juan Bay Cruise 37' Sailboat
Captain Luis and Andrea are the real deal! We spent so much time figuring out the best sailing experience and we couldn’t have been more lucky to have found the of them and this sailing experience from San Juan bay watching the sunset and seeing the beauty of the fort and gorgeous old San Juan!!! They are so seasoned and know the waters so well that our ride was just a peaceful incredible magical ride and was the highlight of our trip!!! Trust me, stop looking and hurry and book. They are worth it and the experience will be for a lifetime!!! Thank you again guys for the beautiful evening for my fiance and I
Top Sailboat Rental Locations in Puerto Rico
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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