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Sailboats
Set sail with these traditional wind-powered boats
$100-$1,250
Kayaks
Who says you need a motor to have fun on the water?
$350-$2,065
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$600-$750
Fishing Charters
Let a captain do the driving while you do the fishing
$250
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$250
CL
Chet
36ft Vintage Yacht Marlinspike Charter in Sag Harbor, New York
Captain Hagen and his boat exceeded our expectations. He set up a neat little mahogany table for our food and supplied ice cold water and ice. The boat is a classic! It was a perfect picnic boat excursion. He took us to a great little cove and anchor so we could swim around while enjoyed our food. Captain Hagen also had some great trivia and pointed out landmarks in the area. Heet us have our privacy and visit with each other, which was nice.
SH
Stephen
36ft Vintage Yacht Marlinspike Charter in Sag Harbor, New York
Captain Hagen is a marvelous human, and took us to some outstandingly beautiful locations in his elegant wooden vessel the MarlinSpike. He hoisted us an English and French flag, as my partner is French and I'm a Londoner. The boat is spacious and there are seats in the back and on the front. Best of all Captain Hagen is multi lingual so very easy to communicate with. Knowledgable about the area around Sag Harbor, and also caring about his passengers, the boat trip was the highlight of our holiday. Thank you Captain Hagen, if we are ever back this way we will take another voyage with you and your skipper, whose name I didn't catch, but both of you made our day. Thank you.
MB
Mark
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Extraordinary experience on a comfortable and beautiful catamaran, with an excellent itinerary from Sag Harbor to Shelter Island for lunch and back. Captain Brian was super professional as was first Mate Erin in implementing and serving our extensive wines and hors d’oeuvres. The vibe of the team was fun, efficient but still chill. I highly recommend this as one of my best summer experiences and I’ve been in here my whole life and I’m in the hospitality business as a boutique hotel owner.
ML
Margaux
A Fully Crewed Luxurious Schooner Perfect for Sails and Events 12 - 41 Guests
We had such a fabulous time on this beautiful boat. Our captain, JM, and the crew Liz and Andrew were so friendly and attentive and amazing with all the kids we had. It was a wonderful afternoon and we can’t wait to do it again!
Ashley
Luxury 38 Express Cruiser - Sag Harbor, Greenport, Shelter Island, Southampton!
The PERFECT summer day! Gary and Connie were absolutely wonderful and so accommodating. The vessel was perfect and in pristine condition! Wish I’d booked for much longer but can’t wait to run it back!
DK
DAVID
36ft Vintage Yacht Marlinspike Charter in Sag Harbor, New York
Our family of 4 had a great time. Terrific Captain, Great boat , Beautiful surroundings , Interesting to see the view of Shelter Island from the water. The Captain shared a lot of knowledge in a very enjoyable manner. Highly recommend the 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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