Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Getmyboat Logo
    All listings in Massachusetts

    Incredible sailboat rentals in Massachusetts, United States.

    5.0
    (232 Reviews)

    Page 1 of 2 • 26 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
    Sailing in Tisbury · 6 guests

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    5.0
    Superowner
    $355/hour
    Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
    Sailing in Salisbury · 2 guests

    Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

    5.0
    $85/hour
    Cal 36 Sailboat Rental in Marblehead, Massachusetts
    Sailing in Marblehead · 6 guests

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    5.0
    $165/hour
    Limited Availability
    42ft J Boat Sailing Yacht in Newport, Rhode Island
    Sailing in Newport · 4 guests

    42ft J Boat Sailing Yacht in Newport, Rhode Island

    5.0
    $260/hour
    Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
    Sailing in Gloucester · 6 guests

    Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

    5.0
    $250/hour
    Providence Private Day Sail Onboard Classic 28' Sabre Yacht Serenity
    Sailing in Providence · 6 guests

    Providence Private Day Sail Onboard Classic 28' Sabre Yacht Serenity

    New
    $150/hour
    Luxury Sailing Catamaran for up to 12
    Sailing in Newport · 12 guests

    Luxury Sailing Catamaran for up to 12

    5.0
    $350/hour
    36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
    Sailing in Stonington · 6 guests

    36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

    5.0
    $220+/hour
    Limited Availability
    Explore Newport Harbor and Narragansett Bay Aboard Beneteau Sense 55 Sailboat
    Sailing in Newport · 6 guests

    Explore Newport Harbor and Narragansett Bay Aboard Beneteau Sense 55 Sailboat

    5.0
    $400/hour
    Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht
    Sailing in New Bedford · 6 guests

    Spend the Day on Buzzards Bay - Sail on "Omoo" a Pearson 35 Cruising Yacht

    5.0
    $260+/hour
    Custom Sailing Charter - Newport/ Block Island
    Sailing in Newport · 6 guests

    Custom Sailing Charter - Newport/ Block Island

    5.0
    $450/hour
    Charter 36ft Sloop In Westbrook, Connecticut
    Sailing in Westbrook · 6 guests

    Charter 36ft Sloop In Westbrook, Connecticut

    5.0
    $250/hour
    Limited Availability
    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
    Sailing in Newport · 6 guests

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    5.0
    $180/hour
    Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
    Sailing in Salisbury · 4 guests

    Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

    5.0
    $160/hour
    43' Sailboat, Bristol RI & Beyond
    Sailing in Bristol · 6 guests

    43' Sailboat, Bristol RI & Beyond

    5.0
    $159+/hour
    Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts
    Sailing in Salem · 6 guests

    Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

    5.0
    $550/hour
    Private Sailing Charter on Martha's Vineyard
    Sailing in Tisbury · 6 guests

    Private Sailing Charter on Martha's Vineyard

    5.0
    $45+/hour
    Limited Availability
    Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Endeavor Sailboat
    Sailing in Newport · 6 guests

    Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Endeavor Sailboat

    5.0
    $300/hour
    Narragansett Bay Sailing Onboard Classic 36' Hunter Yacht
    Sailing in Warwick · 6 guests

    Narragansett Bay Sailing Onboard Classic 36' Hunter Yacht

    New
    $150/hour
    Limited Availability
    Sail Gloucester Harbor and Beyond on a Private 36ft Sailing Catamarant!!
    Sailing in Gloucester · 6 guests

    Sail Gloucester Harbor and Beyond on a Private 36ft Sailing Catamarant!!

    5.0
    $225+/hour
    Sail & Stay in Nantucket – Private Charters + Overnight Aboard a Beneteau 36.7
    Sailing in Nantucket · 6 guests

    Sail & Stay in Nantucket – Private Charters + Overnight Aboard a Beneteau 36.7

    New
    $320+/hour
    Mattapoisett Sailboat Cruise - 42ft "Our Passion"
    Sailing in Mattapoisett · 6 guests

    Mattapoisett Sailboat Cruise - 42ft "Our Passion"

    New
    Superowner
    $355/hour
    Martha's Vineyard Best Sailing Charters on 60' Luxury Ketch
    Sailing in Tisbury · 6 guests

    Martha's Vineyard Best Sailing Charters on 60' Luxury Ketch

    New
    $300/hour
    Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston
    Sailing in Boston · 8 guests

    Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

    New
    $550/hour
    Instant Book

    Top Destinations Nearby

    Sailing Reviews in Massachusetts

    1. KS

      Kevin

      Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

      What an amazing trip. I’ve been coming to the waters on the Vineyard for years and Mason took us to places I’ve never seen before. The boat was perfect for a relaxing adventure. I would highly recommend for almost any type of group from a couple to a family or a small group. What an experience !

    2. LF

      Lena

      Newport RI: Sailing, Swimming and Sightseeing Trips on 32' Endeavor Sailboat

      Amazing trip! Eric was fantastic. He asked us what we wanted to do, and he took us to his favorite spots. We went swimming and jumped off rocks. He told us very interesting stories and was extremely friendly. He made the whole experience better. He made us feel like the boat was our own. Great time, amazing boat. I’d definitely book him again!

    3. MS

      Matt

      Explore Newport Harbor and Narragansett Bay Aboard Beneteau Sense 55 Sailboat

      Absolutely top notch, great communication and excellent skill and handling. Gave a great tour and our whole family loved the day. Thank you!

    4. YB

      Yoni

      Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

      He is an excellent captain.

    5. 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!

    6. 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!

    About

    1. About Getmyboat
    2. Careers
    3. Media Inquiries
    4. Terms of Use
    5. Privacy Policy
    6. Cookies Policy
    7. Accessibility Statement
    8. Member Interface Agreement
    9. Sitemap
    10. Contact Us

    Learn More

    1. How It Works
    2. For Owners
    3. Mobile Apps
    4. Safety

    Experiences

    1. Boat Rentals
    2. Jet Ski Rental
    3. Fishing Charters
    4. Houseboat Rental
    5. Pontoon Rental
    6. Yacht Rental
    7. Sailboat Rental
    8. Bachelorette Party Boat Rental
    9. Party Boat Rentals

    Journal

    1. Company News
    2. Lifestyle
    3. Experiences Guide
    4. Destinations
    5. Tips for Renters and Owners

    Popular Destinations

    1. Miami
    2. Lake Lanier
    3. Lake Tahoe
    4. San Diego
    5. Lake Travis
    6. Newport Beach
    7. Chicago
    8. Lake Norman
    9. Key Largo
    10. Destin
    11. Marathon

    24/7 Live Support

    1. Help & FAQs
    2. +1 818 927 2148
    3. support@getmyboat.com

    Real reviews from happy Getmyboaters.

    4.9 out of 5! 500,000+ reviews

    • Download on the App Store
    • Get it on Google Play
    © Getmyboat 2026
    TermsPrivacy