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Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$385
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$185-$1,235
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$45-$540
Fishing Charters
Let a captain do the driving while you do the fishing
$50-$375
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$60-$380
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$440
Kayaks
Who says you need a motor to have fun on the water?
$30-$1,075
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$250-$1,200
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$85-$315
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$110-$275
Rafting
A high-energy adventure for the whole family
$150
AB
Amanda
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
My family and I had a spectacular sailing adventure. Mason and Lynn are friendly and professional and really made us feel welcome. They gave us an experience that we will never forget. The boat had plenty of room for all of us to enjoy sightseeing and even allowed some on board fishing. We had never sailed before and after our time with Mason and Lynn, we can’t wait to sail with them again. If you’re looking for an unforgettable time on the water, I recommend sailing with them. ⭐️⭐️⭐️⭐️
WI
Whitney
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Capt Ken was fantastic - highly recommended for small groups especially with kids. Ken was super communicative leading up to the trip, and provided a custom experience (finding a good spot to swim), he even let the kids steer the boat. The Mariah is a beautiful vessel with comfortable seating as well as roomy and shady as needed. I would book with Ken again no questions. Thank you, Ken!!
DK
Dmitri
Charter 36ft Sloop In Westbrook, Connecticut
We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!
DS
Danielle
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
From start to finish, Kenneth was incredibly friendly and engaging, making the entire experience unforgettable. He truly made us feel like part of the sailing adventure, sharing his knowledge and ensuring we had the best time possible. I would rate this experience a 10 out of 10 and would gladly book with him again next time we're in town. Highly recommend!
AN
Alexis
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
My husband and I booked this excursion with Mason and Lynn for the 4th of July weekend, and it was the best part of the entire weekend! Mason and Lynn were incredibly hospitable and caring, communicative, and thoughtful. Mason suggested taking the day to go to Cuttyhunk and it was worth it. We had the best lobster rolls of our lives and walked around the town. It was a magical day. The boat was beautiful and Mason and Lynn went out of their way to make sure we had a great day. Highly highly recommend!
JA
Jeremy
Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast
Ralph made bareboating a great experience end to end. His Morgan 36-5 Nelson Marek was just right, in working order and easy to sail for just my wife who does not sail and me. The equipment was all good, including a new and simple to use chart plotter mounted right at the helm. Beautiful location, conditions and waters made for great sailing. Convenient getting answers in advance, getting started and finished. All good. Highly recommendation. And there’s a super lobster place right nearby.
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!
December 11, 2019
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August 01, 2023
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October 03, 2022
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August 12, 2021
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July 19, 2021
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December 30, 2019
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