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The Best Sailboat Rentals in Gloucester
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Gloucester
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$260-$1,070
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$235-$390
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$250-$385
Fishing Charters
Let a captain do the driving while you do the fishing
$250-$385
Top Sailboat Rental Locations Near Gloucester
Marblehead, Massachusetts
7 boats to rent
Hull, Massachusetts
11 boats to rent
Boston, Massachusetts
55 boats to rent
Quincy, Massachusetts
42 boats to rent
Barnstable, Massachusetts
15 boats to rent
Cape Cod, Massachusetts
29 boats to rent
Chatham, Massachusetts
7 boats to rent
Lake Winnipesaukee, New Hampshire
7 boats to rent
Middletown, Rhode Island
16 boats to rent
Newport, Rhode Island
21 boats to rent
Jamestown, Rhode Island
21 boats to rent
Narragansett, Rhode Island
24 boats to rent
Montauk, New York
44 boats to rent
Sag Harbor, New York
46 boats to rent
Noyack, New York
42 boats to rent
Southampton, New York
69 boats to rent
Long Island, New York
62 boats to rent
Fire Island, New York
10 boats to rent
Recent Reviews in Gloucester
Brad
Cal 36 Sailboat Rental in Marblehead, Massachusetts
We had a great day on the water with Captain Alan. Highly recommend this charter. Captain Alan is a knowledgeable and affable sailor. The trip consisted of myself and my wife, our twenty two year old daughter, and her two friends; the boat was easily accommodated all of us, Captain Alan and his first mate. Highly recommend Marblehead and the North Shore area for convenient and scenic sailing. We were even able to swim off the boat. Great day!
WF
William
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Outstanding captain, flexible schedule, based on wind conditions. Knowledgeable captain, plan b to view the seals during calm wind conditions, that kept my grandsons (8,10) entertained. First mate Mable , very helpful, both with the boat and the boys.
KB
Kerry
Cal 36 Sailboat Rental in Marblehead, Massachusetts
My sisters and I had a wonderful experience with Captain Allan Waldman. We rented the Emma Rose to take our mother’s ashes and scatter them in the ocean out of Marblehead Harbor, where the boat is conveniently located. We were transported to and from the boat by independent launch from Commercial Street Wharf. The weather was luckily beautiful and the trip was made quite memorable by Captain Allan’s sensitivity to our needs. He is comfortable with people and gave us the time to absorb the experience we had and also enjoy the beauty of the afternoon.
DB
Dylan
Cal 36 Sailboat Rental in Marblehead, Massachusetts
I booked this trip to propose to my girlfriend and Allen made this very memorable. The harbor and surrounding area in Marblehead was beautiful, and seeing all the other sails in the horizon is a scene that makes this experience worth every penny. Allen was friendly and very knowledgeable. I had never been on a sailboat before but the classic look and close quarters seating area of this vessel made for a romantic setting. Absolutely recommend for a date, special occasion, or just a casual sail around the Gold Coast.
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.
Top Sailboat Rental Locations in the United States
Los Angeles, California
373 boats to rent
San Francisco, California
79 boats to rent
Miami, Florida
1081 boats to rent
Marina del Rey, California
132 boats to rent
Oakland, California
46 boats to rent
Honolulu, Hawaii
45 boats to rent
San Diego, California
107 boats to rent
New York, New York
78 boats to rent
Annapolis, Maryland
47 boats to rent
Dania Beach, Florida
238 boats to rent
Fort Lauderdale, Florida
258 boats to rent
Charleston, South Carolina
128 boats to rent
Chicago, Illinois
287 boats to rent
Hitchcock, Texas
50 boats to rent
Texas City, Texas
41 boats to rent
Tampa, Florida
410 boats to rent
Houston, Texas
52 boats to rent
Baltimore, Maryland
46 boats to rent
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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Real reviews from happy Getmyboaters.
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