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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$175-$3,575
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$55-$2,830
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$2,285
Kayaks
Who says you need a motor to have fun on the water?
$25-$3,540
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$2,355
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$25-$4,540
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$100-$150
Diving
Explore the ocean depths with trained boat operators
$2,200-$2,900
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$115-$265
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$400-$490
CB
Claudia
Private Luxury Sailing Experience out of Old San Juan
Absolutely beautiful 40-feet sailboat, pristine and immaculate. We were a group of 10 and had a great sunset sail to Old San Juan. Captain William and Manu were superb and made it a memorable experience. Thank you one again! We will repeat.
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
SD
Sarah
Private San Juan Bay Cruise 37' Sailboat
My husband, 2 small kids, and I went on a morning 4 hour sail with Luis and Andrea. Luis and Andrea were kind and always looking out for us enjoying our experience. Our kids had lots of fun and my husband and I were able to relax and enjoy the scenery. I 100% recommend booking a cruise with Captain Luis!
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.
Celena
Private San Juan Bay Cruise 37' Sailboat
Captain Luis and Andrea provided a beautiful sail by Old San Juan. They anchored for us and my husband and I were also able to jump in and swim. We had a great day on the water. Highly recommend.
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!
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!
September 05, 2023
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February 18, 2022
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December 13, 2021
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August 01, 2023
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October 03, 2022
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August 12, 2021
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