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    Incredible sailboat rentals in Massachusetts, United States.

    Average of 191 reviews in this area.
    1 - 18 of 24 listings
    Experience Newport RI with us! - Charter Sailing Yacht
    hour$265
    6 guests

    Experience Newport RI with us! - Charter Sailing Yacht

    42ft Monohull Sailboat in Newport, Rhode Island
    hour$225
    4 guests

    42ft Monohull Sailboat in Newport, Rhode Island

    50 ft Sail Yacht with Young & Fun Crew :)
    hour$250
    6 guests

    50 ft Sail Yacht with Young & Fun Crew :)

    4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!
    hour$150
    4 guests

    4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

    Tandem Sail on TWO Classic Sailboats (Or Just Charter One)
    hour$175
    12 guests

    Tandem Sail on TWO Classic Sailboats (Or Just Charter One)

    Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat
    hour$250
    6 guests

    Sail the Thimble Islands on the classy 35' Dufour 4800 Sailboat

    46' sailing yacht  SolMate,  Providence and Narragansett Bay Islands
    hour$235
    6 guests

    46' sailing yacht SolMate, Providence and Narragansett Bay Islands

    Charter 36ft Sloop In Westbrook, Connecticut
    person$145
    6 guests

    Charter 36ft Sloop In Westbrook, Connecticut

    Fun 23' Sonar Sail Boat for Up to 5 Guests
    hour$200
    5 guests

    Fun 23' Sonar Sail Boat for Up to 5 Guests

    Captained Sailboat Charter in Salisbury 2 hr sails
    hour$85
    4 guests

    Captained Sailboat Charter in Salisbury 2 hr sails

    41' Catana Cruising Catamaran for Charter in Newport, RI
    hour$275
    6 guests

    41' Catana Cruising Catamaran for Charter in Newport, RI

    25' Catalina Classic Pocket Cruiser
    hour$100
    4 guests

    25' Catalina Classic Pocket Cruiser

    60' Cruising Monohull Ketch in Vineyard Haven, MA
    week$7
    6 guests

    60' Cruising Monohull Ketch in Vineyard Haven, MA

    Able Custom 42' Chartered Sailing Experience in Stonington, CT
    hour$215
    3 guests

    Able Custom 42' Chartered Sailing Experience in Stonington, CT

    24 results

    Boating Guide - Massachusetts Sailing

    Rent or charter a sailboat for a memorable experience in Massachusetts.

    Are you ready for a fun adventure out on the open water onboard a sailboat in Massachusetts? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Massachusetts is a wonderful sailboat rental destination.

    Using GetMyBoat to book your next sailing experience.

    Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

    Search for the perfect experience now and book your dream day out on the water.

    GetMyBoat customer reviews for Sailing in Massachusetts.

    1. BM
      Bruce
      4 or 8 Hour Sails on Narragansett Bay on Seafarer Swiftsure Yacht!

      Joe's 1978 cruising sailboat was just the right size and weight to balance comfort with sailing experience. Joe was highly knowledgeable as a sailor and with sharing the local lore. It felt more like a sail with friends than a "charter." As a former sailor myself, I felt totally at ease in his hands. We plan to make this a regular part of our visits to Providence.

    2. ML
      Meaghan
      50 ft Sail Yacht with Young & Fun Crew :)

      Steve gave us a truly memorable experience. We wanted a trip to honor the memory of a friend who sailed the harbor, and Steve was so accommodating and thoughtful in helping us plan the day. He has so much knowledge of sailing and of the area. We could't have asked for a better captain.

    3. BL
      Brian
      50 ft Sail Yacht with Young & Fun Crew :)

      Simply perfect. Couldn’t have written a better experience. This crew rocks!

    4. AS
      Anthony
      Experience Newport RI with us! - Charter Sailing Yacht

      We (4 adults and two seven year-old boys) had a lovely four-hour sail with Patrick and Monika. They were the perfect hosts, sharing both their gorgeous boat and their day with us out on the water. There was plenty of space to relax on-board while Patrick pointed out sights of interest and even stopped along the journey so that the two boys could take a dip in the bay during our sail. Could not have asked for a more perfect Sunday afternoon in Newport!

    5. Sarah
      Sarah
      Experience Newport RI with us! - Charter Sailing Yacht

      Once we booked our trip, Patrick always returned our messages quickly, usually within an hour. We were a party of 6 with 4 adults and 2 children. The boat is beautiful. We were free to move around the boat and sit up front. There isn’t a lot of space to fit everyone in the back, but with a couple people in the front, it’s perfect. Patrick was knowledgeable about the mansions and area. Overall we had a great sail!

    6. MK
      Marissa
      Experience Newport RI with us! - Charter Sailing Yacht

      Patrick and Monika were wonderful! They were easy to communicate and coordinate with and were very timely. The boat was great - equipped with a speaker and blankets that we forgot! Their knowledge of the Newport area was very fun and informative! We had a great time sailing around the area - would definitely recommend!

    GetMyBoat has 24 listings for Sailing experiences in Massachusetts with 191 reviews.

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