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Wareham, Massachusetts Boat Rentals & Yacht Charters

Page 1 of 124 listings

Relax Aboard The Classic Motor Yacht Gypsy in Southern New England
Events in Bourne · 6 guests

Relax Aboard The Classic Motor Yacht Gypsy in Southern New England

New
$120/hour
Mattapoisett Sailboat Cruise - 42ft "Our Passion"
Sailing in Mattapoisett · 6 guests

Mattapoisett Sailboat Cruise - 42ft "Our Passion"

New
Superowner
$355/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
Fairhaven/New Bedford Escape – Sail Buzzards Bay in a Classic Sloop
Sailing in Fairhaven · 6 guests

Fairhaven/New Bedford Escape – Sail Buzzards Bay in a Classic Sloop

5.0
$150/hour
Yamaha 195S Wakeboat in Sandwich MA
Powerboats in Sandwich · 8 guests

Yamaha 195S Wakeboat in Sandwich MA

5.0
$750/day
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
Cruise and Dine — Explore the Cape, Cuttyhunk and Martha’s Vineyard by Boat!
Events in Fairhaven · 6 guests

Cruise and Dine — Explore the Cape, Cuttyhunk and Martha’s Vineyard by Boat!

New
$249/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
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
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
Private Sailing Charter on Martha's Vineyard
Sailing in Tisbury · 6 guests

Private Sailing Charter on Martha's Vineyard

5.0
$45+/hour
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
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
Boston Luxury Cruise – Chaparral Signature 24  Private Captain & First Mate
Powerboats in Fall River · 6 guests

Boston Luxury Cruise – Chaparral Signature 24 Private Captain & First Mate

New
$325/hour
Spend a day of sun and fun aboard our 42’ Silverton Motor Yacht
Events in Fall River · 6 guests

Spend a day of sun and fun aboard our 42’ Silverton Motor Yacht

5.0
$300/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
$275/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
$375/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
$174/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
$995/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
22' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 9 guests

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

New
$375/hour

Wareham Reviews

  1. Kasheena

    Kasheena

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    Yesterday’s sailing experience was simply amazing. The captain and crew went above and beyond to take care of our family and make sure all of our needs were met. Even when we were caught up in the moment, they made sure to point out the incredible sights and beauty of the Vineyard so we would not miss a thing. Their kindness, attention to detail, and genuine care made the whole experience unforgettable. We had such a wonderful time and will definitely charter with them again when we return.

  2. 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 !

  3. TI

    Tony

    Fairhaven/New Bedford Escape – Sail Buzzards Bay in a Classic Sloop

    I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.

  4. 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 !

  5. Dhuvi

    Dhuvi

    Yamaha 195S Wakeboat in Sandwich MA

    If this is the only review you read, all you need to know is that you wont find a better boat or boat renter. The 195s is an insanely fun ride and very beginner friendly (rare combination) and Caleb has excellent communication and is super accommodating. Youd be hard pressed to find things that could have made our experience better.

  6. RA

    Rob

    Yamaha 195S Wakeboat in Sandwich MA

    It took a little learning to use the GetMyBoat website/app. Boat owner Caleb W. was very responsive to messages. You won’t have to wait long to hear from him, most often in minutes, and that didn’t change after the booking. He was prompt in meeting at the boat ramp and the end of the rental day. He was very helpful to accommodate where we wanted to put in the boat in Waquoit Bay or Barnstable Harbor. With the little extra time Caleb provides over the ‘boat rental businesses’ elsewhere, we could cruise more leisurely between Waquoit Bay and Falmouth area and still enjoy anchoring in the shallow water of Washburn Island to enjoy getting in the water. Try to do your boating in waters under 2 1/2 foot seas to enjoy the front of the boat.