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Sailboats
Set sail with these traditional wind-powered boats
$105-$1,170
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$250-$750
Kayaks
Who says you need a motor to have fun on the water?
$325-$400
Fishing Charters
Let a captain do the driving while you do the fishing
$130-$250
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$130-$250
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$675
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.
SB
Scott
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
What a day on the water! Our Group of 7 people had an awesome time Captain Brian & Erin. The Catamaran was huge! The sun deck and the interior were clean and full of amenities. The Sailing around Sag Harbor and Shelter Island was something that we will never forget.
Mayuri
A Fully Crewed Luxurious Schooner Perfect for Sails and Events 12 - 41 Guests
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
Captained Hinckey 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.
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.
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!