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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$250-$5,500
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$250-$92,160
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$250-$92,160
Kayaks
Who says you need a motor to have fun on the water?
$3,000
SH
Sondra
Private Luxury Sailing Charter around the East Coast of Puerto Rico
Fantastic day! Gio and Angie went above and beyond to make our day special. They even took extra time to accommodate our dietary requirements and presented our daughter with a special Birthday treat. Thank you so much for everything.
NR
Na
Private Tours & Snorkeling at Icacos & Palomino Islands- Grady White 27'
Incredible experience! Jose was wonderful and very attentive. He made sure we were all having an amazing time which we really appreciated. Many thanks to the Black Octopus team for an unforgettable day!
CS
Claudia
Private Tours & Snorkeling at Icacos & Palomino Islands- Grady White 27'
Jose was amazing! He was our tour guide, photographer, snack grabber- he was at our beck and call and took such great care of us! Such a fun time with all the water toys too! This charter was perfection in every way! Yummy food, snacks, beverages (alcoholic and non) were also provided. Book with Jose for a grand time!
HC
Heather
Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick
Fabulous day with a knowledgeable captain on a very comfortable boat. Captain Rick customized the trip to our group’s every need and preference. He and his assistant Rachel provided an uniquely memorable Caribbean experience we can highly recommend.
RB
Rose
Sailing Cruise Saint John
Book now! This was such a memorable experience! From the line of communication, to Shana amazing Mediterranean platter to captain in training Jaya keeping my son company, it was amazing! From pick up to drop off such a wonderful experience. We cannot wait to see them again this time hopefully in Maine!
JP
Jeff
Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!
What a wonderful day at sea! Four of us joined Rosie , Brad and mascot Bozun for a day of sailing and snorkeling. The customer service was top notch. The food was some of the best we had on St. Thomas and Rosie's presentation was so appetizing. While snorkeling we saw an octopus, a barracuda, an eagle ray and countless beauftiful coral, fish and sea urchins. Our hosts chronicled our day and we received pictures and videos of our experiences. We would definitely recommend Rosie and Brad.
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
August 01, 2023
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October 03, 2022
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August 12, 2021
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July 19, 2021
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December 30, 2019
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December 26, 2019
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