We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.
Sailboats
Set sail with these traditional wind-powered boats
$95-$1,030
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$125-$750
Fishing Charters
Let a captain do the driving while you do the fishing
$130-$250
Kayaks
Who says you need a motor to have fun on the water?
$25-$400
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
$150-$215
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$110-$500
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.
NS
Nicholas
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Marco was a wonderful captain and we had a great time watching fireworks from Todd's Point on the water. He piloted the ship safely and got us "front row seats" for the show. He also was mindful of other boaters in the area and got us out before the show ended so we weren't stuck or in danger. This was a surprise for my partner and Marco made it so worth the wait to reveal that we were going on an adventure in this beautifully renovated, fully equipped and well maintained ship. Would do this trip over 100 times! I highly recommend Marco for anyone that wants a safe, comfortable, and truly special time on the water.
BS
Bonnie
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Marco is the perfect captain. Extremely knowledgeable about boats, navigates the waterways with great confidence, and truly loves what he does. The boat is very clean, maintained beautifully, and the day was perfect. I would definitely sail with Marco again. Great experience!
CM
Cynthia
28' Bertram around islands in Norwalk
My party of 11 and I had a great time with Mark and his crew. He communicated promptly regarding weather conditions and what to expect on the boat. He was knowledgeable about the surrounding areas and the boat itself. This was a perfect experience to enjoy the water in CT for any special occasion or just a nice summer day with friends or family. We will definitely be returning to this charter !!
JS
Jillian
28' Bertram around islands in Norwalk
Couldn’t ask for a better captain or boat! Mark was great. Extremely friendly, it was a beautiful boat, and it was very clean. We had a great time, and Mark was very knowledgeable on all of the small islands and locations we passed. I would highly recommend booking with him!
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!