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.

All listings in Massachusetts

Incredible tours in Massachusetts, United States.

Page 2 of 243 listings

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
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
Luxe 68ft Fairline w/ A Paddleboard, Kayak & More in Northeast, USA
Events in Westbrook · 12 guests

Luxe 68ft Fairline w/ A Paddleboard, Kayak & More in Northeast, USA

New
$1,475+/hour
51' Ferretti Built Mochi Craft - Dolphin Express Cruiser
Events in Boston · 6 guests

51' Ferretti Built Mochi Craft - Dolphin Express Cruiser

New
$575/hour
Full Day Rental | 220 Dauntless Boston Whaler anywhere on Cape Cod
Powerboats in Barnstable · 9 guests

Full Day Rental | 220 Dauntless Boston Whaler anywhere on Cape Cod

New
$195/hour
Luxe 70ft Azimut w/ a Tender, Jet Ski, Seabob and more. Serving North East, USA
Events in Boston · 12 guests

Luxe 70ft Azimut w/ a Tender, Jet Ski, Seabob and more. Serving North East, USA

New
$1,475+/hour
88ft San Lorenzo w/ Jet Skis, Seabobs, Paddleboard & More serving Northeast, USA
Events in Nantucket · 12 guests

88ft San Lorenzo w/ Jet Skis, Seabobs, Paddleboard & More serving Northeast, USA

New
$18,100/night
Charter this impeccable Sea Ray Sundancer – 50 Foot Cruiser
Events in Portsmouth · 6 guests

Charter this impeccable Sea Ray Sundancer – 50 Foot Cruiser

New
$490+/hour
Striped Bass and Bluefin Tuna Fishing Charter in Truro, Massachusetts (33' Boat)
Fishing in Truro · 6 guests

Striped Bass and Bluefin Tuna Fishing Charter in Truro, Massachusetts (33' Boat)

New
$170+/hour
Newport Cape & Islands Fun & Style- Private Day Yacht
Events in Newport · 8 guests

Newport Cape & Islands Fun & Style- Private Day Yacht

New
$350/hour
Striped Bass and Bluefin Tuna Fishing Charter in Truro, Massachusetts (26' Boat)
Fishing in Truro · 6 guests

Striped Bass and Bluefin Tuna Fishing Charter in Truro, Massachusetts (26' Boat)

New
$140+/hour
Boston Harbor Luxury Cruise | 46ft Silverton Yacht + Captain Included
Events in Quincy · 6 guests

Boston Harbor Luxury Cruise | 46ft Silverton Yacht + Captain Included

New
$550/hour
Charter 25' Steiger Craft Yacht In Quincy, MA.
Powerboats in Quincy · 4 guests

Charter 25' Steiger Craft Yacht In Quincy, MA.

New
$125/hour
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
38' Flybridge Boston Harbor/Islands Boat Days - up to 6 guests
Fishing in Quincy · 6 guests

38' Flybridge Boston Harbor/Islands Boat Days - up to 6 guests

New
$275/hour
Fishing Trip in Essex, Massachusetts with Captain Ted
Fishing in Essex · 6 guests

Fishing Trip in Essex, Massachusetts with Captain Ted

New
$100+/hour
Fast and Fun Fishing or Cruising Boat | 27' Mako Center Console
Fishing in Winthrop · 6 guests

Fast and Fun Fishing or Cruising Boat | 27' Mako Center Console

New
$200/hour
Get Ready To Have Fun Single Jet Ski Rental 2025 Yamaha Jetblaster Deluxe
Water Sports in Westfield · 2 guests

Get Ready To Have Fun Single Jet Ski Rental 2025 Yamaha Jetblaster Deluxe

New
$125+/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

Tours Reviews in Massachusetts

  1. AD

    Alice

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

    Captain Lu is THE MAN ! We had an amazing time with him, he’s very nice and extremely knowledgeable. He adjusted the course of the cruise to an easier swell when our friend that is easily seasick started to feel dizzy, and she felt great the entire time! I can only recommend cruising with Captain Lu and will surely be back again !

  2. 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.