Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Gloucester, Massachusetts Boat Rentals

Page 1 of 110 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
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
Full Day Bluefin Tuna Fishing Charter
Fishing in Salem · 6 guests

Full Day Bluefin Tuna Fishing Charter

New
$260/hour
50ft Viking Half Day Bottom Fishing Charter
Fishing in Salem · 6 guests

50ft Viking Half Day Bottom Fishing Charter

New
$250/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!!

New
$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. 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.

  2. 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.

  3. FB

    Frima

    2 hour harbor cruise around historic Salem Sound

    Our trip with Captain Michael was exceptional! All around delightful experience from start and finish! The boat is clean and very spacious. The Captain and staff member was very engaging and made memorable stops for us to explore the beautiful coastline of the North Shore. Can't wait to go again!

  4. BF

    Brianna

    Large Group Experience : Private Events in Gloucester, Massachusetts

    Best captain/host ever! The boat was beautiful, sound system great, and the people made our night. Everything went so smoothly. Barbara and Jeff were a great time and we can’t wait to hit the water with them again!

  5. EG

    Ece

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Allan and the crew were wonderful. We would absolutely sail with them again!

  6. KB

    Kerry

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    My sisters and I had a wonderful experience with Captain Allan Waldman. We rented the Emma Rose to take our mother’s ashes and scatter them in the ocean out of Marblehead Harbor, where the boat is conveniently located. We were transported to and from the boat by independent launch from Commercial Street Wharf. The weather was luckily beautiful and the trip was made quite memorable by Captain Allan’s sensitivity to our needs. He is comfortable with people and gave us the time to absorb the experience we had and also enjoy the beauty of the afternoon.