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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$80-$440
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$55-$145
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$30-$355
Fishing Charters
Let a captain do the driving while you do the fishing
$70-$105
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$30-$90
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$80-$105
Kayaks
Who says you need a motor to have fun on the water?
$160
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$105
TI
Tony
Sunset Sail Buzzards Bay in a Classic Sloop!
I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.
Heiner
43' Sailboat, Bristol RI & Beyond
We had a wonderful time with Catian Francis :) He is a lot of fun and makes you feel at home on his yacht. Things wemt very smooth and we can highly recommend having a exceptional sailing experience with him. Heiner
MM
Monica
Sailing Adventure Aboard 44' Hunter Sailboat
I cannot rave more about how AMAZING our experience was with Geoff! 1000 stars! It was absolutely beautiful and he made sure we had the best view of the sunset. We booked with him for an engagement photoshoot and he was super professional, fun, and incredibly helpful throughout helping us get the perfect shots. I’d recommend booking with Geoff for any occasion. I will definitely book again! Thanks Geoff!
GT
George
Sailing Adventure Aboard 44' Hunter Sailboat
Geoff was awesome! His sailboat was very clean and he was very accommodating. My wife and I went out to watch the sunset in Portsmouth and the itinerary was perfect. Geoff was really pleasant and we’ll definitely book with him again.
KH
Katherine
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
We had a fantastic experience renting Matt’s sunfish sailboat. He was easy to communicate with, gave excellent instructions, and the boat and lake were an absolute dream. He even pointed us towards a great local spot for ice cream/light bites after the sail. We will definitely be back to rent from Matt again!
Megan
32ft Classic Swedish Sloop Sailing Charter
We had a wonderful sail with Linda on her beautiful boat! It was a really lovely afternoon on the water. The communication about where to meet and weather conditions was clear and easy. She had excellent knowledge of the area as well as great sailing tips. We would book with Linda again!
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!