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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$150
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$160
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$75
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$250
Fishing Charters
Let a captain do the driving while you do the fishing
$75
AP
Abraham
50’ Yacht in Oysterbay, Cruise, Paddleboard, Kayak, Tubing, optional Waverunner
My daughter and her friends had a 16th birthday party on the boat and they had an amazing time. Jeffrey was a wonderful host and the boat was incredible. Everything was exactly as described and it was a amazing experience for everyone.
EB
Ernest
Private Yacht Charter: On 40ft Regal Commodore
GREAT experience!!! Captain Dennis was terrific. He was professional, yet fun & extremely well prepared. The yacht was clean & well maintained with all the amenities that we could ask for. Our only regret is that we did not book a longer cruise on Seas the Day.
MC
Mike
Sailing NYC aboard 34' Catalina
Great experience to see the city! Ian is awesome and knows the city well. Besides the pictures and views, sailing towards the Statue of Liberty was a moving experience. Would definitely recommend to anyone in the area. Thanks Ian!
Abigail
Private Yacht Charter: On 40ft Regal Commodore
Captain Dennis was exceptional—punctual, professional, and allowed us to have a great time. The boat itself was in perfect condition, with all the necessary equipment and some luxurious extras, like the floating 🏝️, that made the day truly enjoyable. The excellent service and the beautiful setting made it an unforgettable birthday party. I highly recommend Captain Dennis for anyone looking to host a memorable and top-notch maritime event.
FG
Fran
"RENT ME" Spacious 38' Cruiser- plenty of room for celebrating or relaxing!!!
Our family had an amazing time on the Kraken. Captain Ken was a gracious host and helped us to create a day that was just what we hoped for. The boat is beautiful and comfortable. We knew we were in the care of a knowledgeable and experienced captain. I would highly recommend Captain Ken and The Kraken. We are still smiling as we remember our day. ☀️🛥️🌊
JF
Joseph
Woman-owned luxury with transparent pricing - read our 5-star reviews!
Jessica and Captain Kevin were exceptional. This was my first charter, it was a last minute booking on a holiday weekend, and for a special occasion (proposal). Jessica was more than prepared and made it so simple! We literally just had to show up. She already communicated the details to the Captain when we arrived. Captain Kevin had the boat prepped and ready to go. We arrived at the private parking, got on the boat (which was beautiful and a perfect size), and enjoyed our experience! Captain Kevin took care of setup, clean up, and even acted as our impromptu photographer at the moment of the proposal. Jessica and her crew are a well oiled machine and I wouldn't hesitate to book with her again for special occasions or simply a day out with friends. I'm living proof, no experience necessary. I look forward to the opportunity to sail aboard Sailing Islander in the future!
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 09, 2023
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November 28, 2022
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May 20, 2021
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December 30, 2019
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December 26, 2019
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