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All listings in Massachusetts

Incredible tours in Massachusetts, United States.

Page 2 of 2 • 44 listings

36' Classic Carolina Classic Boat Rental In Newport, Rhode Island
Powerboats in Newport · 28 guests

36' Classic Carolina Classic Boat Rental In Newport, Rhode Island

4.8
$518/hour
Luxury Voyage – Charter 100ft Calais Mega Yacht in Quincy, Massachusetts
Events in Quincy · 12 guests

Luxury Voyage – Charter 100ft Calais Mega Yacht in Quincy, Massachusetts

New
$1,450/hour
Sail Gloucester Harbor and Beyond on a Private 36ft Sailing Catamaran!!
Sailing in Gloucester · 6 guests

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

5.0
$225+/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

5.0
$550/hour
Instant Book
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
Harbor Breeze Boston — 21ft Key West 21 Dual Console Boat
Powerboats in Cambridge · 8 guests

Harbor Breeze Boston — 21ft Key West 21 Dual Console Boat

New
$250/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
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
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
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
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
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
Fishing Trip in Essex, Massachusetts with Captain Ted
Fishing in Essex · 6 guests

Fishing Trip in Essex, Massachusetts with Captain Ted

New
$100+/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
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
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

Tours Reviews in Massachusetts

  1. CM

    Charneyee

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

    One word! Amazing. Hospitality, equipment. Boat, just beautiful. Me and my family enjoyed every moment. Thank you Capt. Lu 20/10

  2. BH

    Betsy

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

    Oh what a night! We had a fantastic time on our sailing trip with Jake and his crew. They picked us up right on time, we had a perfect sale, and they even gave us some extra time at the end. The views of Boston were perfection, the sale was smooth and we felt very well taken care of by the entire crew the whole time! It really could not have been any more perfect. We highly recommend!

  3. RR

    Robyn

    36' Classic Carolina Classic Boat Rental In Newport, Rhode Island

    Absolutely perfect evening on the water! The short sunset cruise was the highlight of our trip—smooth sailing, stunning views, and a relaxed vibe. The captain was knowledgeable and friendly, and the deckhand made sure everyone was comfortable and had what they needed. Truly a five-star experience—we’d book again in a heartbeat!

  4. AD

    Alice

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

    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 !

  5. 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.

  6. RM

    Ryan

    36' Classic Carolina Classic Boat Rental In Newport, Rhode Island

    Would 100% recommend. Great communication, friendly captain, and wonderful time.