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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$815
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$495
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$500
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$85-$650
Kayaks
Who says you need a motor to have fun on the water?
$10-$470
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$175-$650
Canoes
A classic option for leisurely paddling
$10
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$150
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275
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!
VL
Vincent
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
I booked a trip for my niece and nephew to scatter their mom's (my sister's) ashes. They were very pleased with the service, and it was a perfect day. Communication was fantastic, and the crew was very receptive to their needs. Don't hesitate to book with them!
William
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
2nd sail w/ Rick & Deb. They are warm and entertaining hosts and their boat is a beauty. Wonderful sail last night and we were lucky to catch some wind and get up to 8 knots. A delicious charcuterie board was included. Highly recommend sailing the Artemis with Rick & Deb.
David
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
Rick and Deb create an unmatched experience. Once someone experiences 64’ and multiple sails propelling one through the water…. The comforts, viewing and lounging locations onboard…and the company/conversation with the captain/first mate (Rick and Deb). Anyone will consider this one of the greatest values and investments in experience they have made in a long time. Highly recommend.
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!