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Gloucester, Massachusetts Boat Rentals

Page 1 of 111 listings

Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/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
2 hour harbor cruise around historic Salem Sound
Fishing in Salem · 6 guests

2 hour harbor cruise around historic Salem Sound

5.0
$400/hour
Beautiful  Like New Rinker Fiesta Vee 31' Cruiser
Powerboats in Gloucester · 6 guests

Beautiful Like New Rinker Fiesta Vee 31' Cruiser

New
$175+/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
Instant Book
Large Group Experience : Private Events  in Gloucester, Massachusetts
Events in Gloucester · 46 guests

Large Group Experience : Private Events in Gloucester, Massachusetts

5.0
$499+/hour
50ft Viking Half Day Bottom Fishing Charter
Fishing in Salem · 6 guests

50ft Viking Half Day Bottom Fishing Charter

New
$250/hour
Full Day Bluefin Tuna Fishing Charter
Fishing in Salem · 6 guests

Full Day Bluefin Tuna Fishing Charter

New
$260/hour
Charter a 45ft Boat in Gloucester – Perfect for Parties, Tours & Swims
Events in Gloucester · 31 guests

Charter a 45ft Boat in Gloucester – Perfect for Parties, Tours & Swims

New
$400+/hour
Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!
Sailing in Gloucester · 6 guests

Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

5.0
$175+/hour
Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
Sailing in Gloucester · 60 guests

Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

New
$1,200+/hour

Gloucester Reviews

  1. AD

    Alice

    Sail Gloucester Harbor and Beyond Aboard Catalina 36 MKI Sailing Yacht!!

    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. Brad

    Brad

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    We had a great day on the water with Captain Alan. Highly recommend this charter. Captain Alan is a knowledgeable and affable sailor. The trip consisted of myself and my wife, our twenty two year old daughter, and her two friends; the boat was easily accommodated all of us, Captain Alan and his first mate. Highly recommend Marblehead and the North Shore area for convenient and scenic sailing. We were even able to swim off the boat. Great day!

  3. GP

    George

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Had a great time with Captain Allan, truly a fun time and he was very concerned about us enjoying the experience. We highly recommend him and his service. You won’t be disappointed!

  4. WF

    William

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Outstanding captain, flexible schedule, based on wind conditions. Knowledgeable captain, plan b to view the seals during calm wind conditions, that kept my grandsons (8,10) entertained. First mate Mable , very helpful, both with the boat and the boys.

  5. Joan

    Joan

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Our party of 4 really enjoyed our sail. Captain Allen and first mate Mable were accommodating and nice. Captain Allen is an exceptional sailor and super chill. Highly recommend.

  6. CS

    Candace

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Captain Allen and his crewmate Mable were great! They were very kind and accommodating And easy-going. Even in the pouring rain, they made our trip go well. I would highly recommend them.