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4.9 (4,335 reviews)
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Boat Rentals
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Sailing
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$70
NW
Nicole
May, 2024
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
I hosted my 50th birthday on this vessel!! Absolutely, positively an amazing experience! The vessel is absolutely beautiful and spacious. There was plenty of room on this vessel for my 12 guests! The Captain Shane provided excellent customer service throughout the entire trip. He very responsive to any questions that I had !!! If you want an stellar experience, this is the way to go!!!!!!
SH
Susan
Set Sail with 36' Sailing Boat in Downtown, Chicago
A wonderful May sail. Great boat for 6 people to relax and enjoy the city skyline, while Ray tends to the sailing. Very competent sailor and friendly.
KC
Kevin
April, 2024
Charter 42' Lagoon Catamaran in Annapolis, MD
Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!
HW
Hector
Very professional and yet easygoing captain. Boat was very nice - in excellent shape and well maintained. Highly recommend! We will be back again.
RH
Roger
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Great vessel. Well maintained. Up to date equipment. Very relaxed.
KH
Katie
June, 2021
Charter this Classic Shannon Sailboat w/ Professional Captain in Chicago
Michael was incredible!!! He was so friendly and made our experience so comfortable, relaxing, and fun! I wish he was the captain of every boat I go on moving forward because he was such a wonderful person to have around! Thank you so much Michael! We appreciate your help!
Los Angeles, California
417 listings
Marina del Rey, California
166 listings
San Francisco, California
74 listings
Honolulu, Hawaii
66 listings
New York, New York
84 listings
Oakland, California
43 listings
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
August 12, 2021
July 19, 2021
December 30, 2019
4.9 out of 5! 385,000+ reviews