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4.9 (4,384 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
dr
david
June, 2024
Set Sail with 36' Sailing Boat in Downtown, Chicago
Went on a 3 hour cruise with Captain Dawn and Ted and wow did we have a great time. It’s well worth it to see Chicago from the lake, and no better way to get out on the water than on a sailboat. Will definitely reach out to this group again when I return to Chicago.
CB
Caprice
41' Lagoon Catamaran in Maryland
This was one of the best rides I’ve had in a while. Captain Jess is communicative, helpful and kind. We went out for 4 hours and had great weather. The boat is clean, he had 2 fridges for our food and drinks, it was nice and spacious, and there were floaties to get out on the water. It was a very enjoyable day.
TR
Timothy
May, 2024
35ft C&C 35 Sailboat in Toronto
Peter and the Restless are a wonderful experience. He’s a very knowledgeable and professional individual as well as fun and engaging. The Restless is a great boat and the trip was well worth it! Can’t recommend Peter and his experience more highly.
Arina
37' Luxury Sailing Yacht with Captain in Chicago
We rented Greg’s yacht to celebrate my birthday and it was truly amazing!! The yacht itself was very clean and beautiful and Greg was accommodative and helping us with any requests we had. Thank you!
CE
Celine
We had the most amazing time with Peter. I booked this trip for my fiancé and I’s engagement photoshoot. Peter was very welcoming and helpful throughout the trip. 10/10 would recommend it for everyone! Thank you Peter!
DB
Dan
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Capt Alberto and Grace were wonderful hosts. They were very flexible regarding the weather, great teachers of sailing, and were very hospitable and welcoming with their boat. We had an amazing time. Capt Alberto truly loves the sea.
Los Angeles, California
435 listings
Marina del Rey, California
175 listings
San Francisco, California
77 listings
Honolulu, Hawaii
67 listings
New York, New York
85 listings
Oakland, California
46 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
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December 30, 2019
4.9 out of 5! 500,000+ reviews