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Tisbury, Massachusetts Boat Rentals

Page 1 of 124 listings

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
$250/hour
Private Sailing Charter on Martha's Vineyard
Sailing in Tisbury · 6 guests

Private Sailing Charter on Martha's Vineyard

5.0
Snoozed - Active 02 Jul 2026
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
Snoozed - Active 03 May 2026
28ft Whitewater Center Console Rental in Mashpee, Massachusetts
Powerboats in Mashpee · 6 guests

28ft Whitewater Center Console Rental in Mashpee, Massachusetts

5.0
$300/hour
Spend the Day on Buzzards Bay - Aboard Petrel a classic Dyer 29
Tours in Mattapoisett · 6 guests

Spend the Day on Buzzards Bay - Aboard Petrel a classic Dyer 29

5.0
$200+/hour
8 Person Center Console Rental in Osterville Massachusetts
Powerboats in Barnstable · 8 guests

8 Person Center Console Rental in Osterville Massachusetts

5.0
$275/hour
27' Blackfin Center Console in Osterville & Barnstable, Cape Cod
Powerboats in Barnstable · 6 guests

27' Blackfin Center Console in Osterville & Barnstable, Cape Cod

5.0
$350/hour
39' Yellowfin with Quad Engines, Fast & Fun, Cape Cod & the Islands
Powerboats in Barnstable · 10 guests

39' Yellowfin with Quad Engines, Fast & Fun, Cape Cod & the Islands

New
$1,000/hour
Fairhaven/New Bedford - Sail Buzzards Bay in a Classic Sloop!
Sailing in Fairhaven · 6 guests

Fairhaven/New Bedford - Sail Buzzards Bay in a Classic Sloop!

5.0
$150/hour
Mattapoisett Sailboat Cruise - 42ft "Our Passion"
Sailing in Mattapoisett · 6 guests

Mattapoisett Sailboat Cruise - 42ft "Our Passion"

New
Superowner
$250/hour
Yamaha 195S Wakeboat in Sandwich MA
Powerboats in Sandwich · 8 guests

Yamaha 195S Wakeboat in Sandwich MA

5.0
$500/day
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
$180/hour
Padanaram / Dartmouth Harbor Sailboat Cruise 42ft "Our Passion"
Sailing in Dartmouth · 6 guests

Padanaram / Dartmouth Harbor Sailboat Cruise 42ft "Our Passion"

5.0
Superowner
$250/hour
Come onboard the 45ft Tiara Sovran Motor Yacht
Powerboats in Fairhaven · 10 guests

Come onboard the 45ft Tiara Sovran Motor Yacht

5.0
$399/hour
26’ Regulator Center Console Powerboat Rental in Hyannis Harbor Cape Cod
Powerboats in Barnstable · 12 guests

26’ Regulator Center Console Powerboat Rental in Hyannis Harbor Cape Cod

New
$250/hour
18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 8 guests

18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$690/day
18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 8 guests

18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$119/hour
17′ Montauk Center Console Boston Whaler in Hyannis Harbor - Cape Cod
Powerboats in Barnstable · 5 guests

17′ Montauk Center Console Boston Whaler in Hyannis Harbor - Cape Cod

New
$99/hour
18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 7 guests

18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$690/day
18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 7 guests

18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

5.0
$119/hour
20' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 9 guests

20' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$144/hour
22' Godfrey Sweetwater Pontoon Boat in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 12 guests

22' Godfrey Sweetwater Pontoon Boat in Hyannis Harbor, Massachusetts - Cape Cod

New
$895/day
22' Godfrey Sweetwater Pontoon Boat 12 people in Hyannis Harbor - Cape Cod
Powerboats in Barnstable · 12 guests

22' Godfrey Sweetwater Pontoon Boat 12 people in Hyannis Harbor - Cape Cod

New
$174/hour
26’ Regulator Center Console in Hyannis, Massachusetts - Cape Cod
Powerboats in Barnstable · 12 guests

26’ Regulator Center Console in Hyannis, Massachusetts - Cape Cod

New
$1,595/day

Tisbury Reviews

  1. 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!

  2. SM

    Sarah

    Yamaha 195S Wakeboat in Sandwich MA

    Caleb was incredibly helpful! He came to pick us up by boat and brought us back right in front of our house. He knew all the best spots in the area to stop for a nice lunch. His boat is very comfortable, and he was also great with our little girl. We 100% recommend him !

  3. 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!

  4. 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.

  5. Rodney

    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

  6. 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!!!