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Sailboats
Set sail with these traditional wind-powered boats
$100-$1,140
Fishing Charters
Let a captain do the driving while you do the fishing
$130-$395
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$130-$395
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$145-$750
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$675
SS
Sarah
Explore Sag Harbor on 32ft Defiant Monterey 328 SS Motor Yacht!
10/10 would recommend this experience. Mike was super communicative and flexible in terms of timing and pickup/drop off. He answered all of my messages with lightening speed. The boat was perfect for a group of 7 of us, and we had a great day! Would definitely charter with Mike again!
Mayuri
A Luxuriously Appointed Schooner Perfect for Casual Sails and Events up to 41
If you are looking for an amazing time, do not hesitate booking the Luna! Toby and his staff take care of you every step of the way. The boat is well equipped with servingware, water, and ice for your event. Fun bean bags are plenty aboard. Our guests enjoyed the awning and swim spot on a hot day, as well. Just a fabulous experience from start to finish!
jn
justin
The Picnic Boat “Soleil” -a Meticulous Icon of Hand Crafted Luxury
These guys are total pro’s, super attentive, great to spend the day with and thought of everything before we could even ask. Absolutely gorgeous boat. Toby is super responsive via text and calls. He has a ton of local knowledge and will help craft the perfect day on the water. We cruised around shelter, out to orient for lunch, back to shelter and then back to Sag Harbor. Perfect day on a gorgeous boat with great people. Many thanks.
DR
Devon
Charter 50' Beneteau Gran Turismo from Montauk, New York
Unbelievable!! Thank you Sean and Sean Jr.!! We were so lucky and had a perfect weather day on May 12th. Sean was so friendly, accommodating, and knowledgeable not to mention the boat was pristine. It was a short trip and we wish we had more time but he made it so worth it. Thank you again for making it happen. We will absolutely be returning and giving you a call. Devon Richardson
TC
Trevor
Vintage Yachting Lifestyle in the Hamptons NY
We could not have asked for a better trip with Eric and Eric. The boat was incredible and even more spacious than we imagined, both Eric's were extremely hospitable and overall it was a blast. Truly surpassed our expectations in all ways.
JP
Julia
36ft Vintage Yacht Marlinspike Charter in Sag Harbor, New York
Captain Hagan was a wonderful host on his boat for my friends and I. We got to anchor and explore a little remote island and showed us a few famous homes along the trip. We would use him again in a heartbeat for our next trip!
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 11, 2019
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August 24, 2023
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April 10, 2020
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December 30, 2019
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