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The Best Sailboat Rentals in Massachusetts
Browse, book, and get out onto the water with local captains and boat owners.
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Types of Boats Popular in Massachusetts
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$150-$1,080
Fishing Charters
Let a captain do the driving while you do the fishing
$120-$930
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$120-$940
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$120-$635
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$170-$820
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$90-$920
Kayaks
Who says you need a motor to have fun on the water?
$55-$290
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275-$300
Top Sailboat Rental Locations Near Massachusetts
Boston, Massachusetts
53 boats to rent
Quincy, Massachusetts
39 boats to rent
Cape Cod, Massachusetts
29 boats to rent
Jamestown, Rhode Island
20 boats to rent
Newport, Rhode Island
19 boats to rent
Middletown, Rhode Island
16 boats to rent
Barnstable, Massachusetts
15 boats to rent
Hull, Massachusetts
9 boats to rent
Marblehead, Massachusetts
8 boats to rent
Recent Reviews in Massachusetts
SB
Sarah
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Our sail with David was wonderful! He’s so nice and had some great ideas for pictures for our engagement shoot!
MS
Melvin
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Capt. Mason and Capt. Lynne are ABSOLUTELY AWESOME. Their 42' sail boat was incredible and my party of 5 had a fantastic time on our charter. They are knowledgable, accommodating and true sailors through and through. My wife and I HIGHLY recommend Capt. Mason for any charter needs you may have, using his yacht or any other!
SS
Stephanie
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Mason and Lynne were amazing captains on a private sail charter! So easy to communicate with throughout my planning process and amazing people overall! Had a great time being on the boat with them! Would absolutely recommend them and this experience!
JS
Jonathan
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
An afternoon on the water aboard the Our Passion is like an afternoon in paradise. The sailboat is gorgeous and comfortable, the skipper and crew more like instant old friends, and there’s no better place to sail than Martha’s Vineyard. An 11 out of 10 experience.
Rodney
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Highly recommend if you’re looking for something different to do than what all the other tourists are doing when visiting Martha’s Vineyard, you might want to consider contacting Mason for a peaceful & relaxing sailboat ride to see the beautiful coastline of MV that most don’t get to experience while on land. We’ll definitely be back next year to do another trip
GE
Gerald
Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
By far the best part of our trip to Martha’s Vineyard and the highlight of my girlfriend’s birthday was our time on Captain Mason and Captain Lynne’s boat. They thought of every detail, including birthday decorations and helping me with multiple surprises, took us to the most beautiful spots along the coast and harbor, and even let us partake in a super unique light show boat parade experience. This is by far the best value for money and most unique and relaxing / beautiful experience you could have in the Vineyard. Please trust me and book! Mason and Lynne are also wonderful people who really try to make your experience as amazing as possible. Thank you so much for everything!!!
Top Sailboat Rental Locations in the United States
Los Angeles, California
351 boats to rent
Miami, Florida
1012 boats to rent
San Francisco, California
74 boats to rent
Marina del Rey, California
131 boats to rent
Honolulu, Hawaii
47 boats to rent
Oakland, California
43 boats to rent
San Diego, California
112 boats to rent
New York, New York
78 boats to rent
Annapolis, Maryland
47 boats to rent
Dania Beach, Florida
233 boats to rent
Fort Lauderdale, Florida
251 boats to rent
Chicago, Illinois
258 boats to rent
Hitchcock, Texas
52 boats to rent
Texas City, Texas
42 boats to rent
Charleston, South Carolina
128 boats to rent
Tampa, Florida
413 boats to rent
Saint Petersburg, Florida
269 boats to rent
Newport Beach, California
121 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!
Real reviews from happy Getmyboaters.
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