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Boat Rentals
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the United States
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Massachusetts
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Gloucester
Fishing Charters
Let a captain do the driving while you do the fishing
$100-$500
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$100-$500
Sailboats
Set sail with these traditional wind-powered boats
$150-$1,150
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$300-$1,150
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$400-$500
BV
Boris
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Experienced captain, fun to chat with, excellent sailing skills, will allow to steer the boat which was huge fun. Overall will highly recommend. Thank you Allan!
VL
Vincent
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
I booked a trip for my niece and nephew to scatter their mom's (my sister's) ashes. They were very pleased with the service, and it was a perfect day. Communication was fantastic, and the crew was very receptive to their needs. Don't hesitate to book with them!
NT
Namrata
Cal 36 Sailboat Rental in Marblehead, Massachusetts
We have a wonderful evening aboard Emma Rose. Captain Allen was very accommodating to change the sail date when our original date was rained out. Gave us a great history of the area.
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.
DB
Dylan
Cal 36 Sailboat Rental in Marblehead, Massachusetts
I booked this trip to propose to my girlfriend and Allen made this very memorable. The harbor and surrounding area in Marblehead was beautiful, and seeing all the other sails in the horizon is a scene that makes this experience worth every penny. Allen was friendly and very knowledgeable. I had never been on a sailboat before but the classic look and close quarters seating area of this vessel made for a romantic setting. Absolutely recommend for a date, special occasion, or just a casual sail around the Gold Coast.
BG
Briana
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Awesome experience & an amazing captain. The trip was relaxing and fun. Allan is super experienced, kind, and knowledgeable. He managed to smoothly sail through a sailboat race, without interfering with the race and showed us cute seals and beautiful mansions !!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
August 01, 2023
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November 23, 2022
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October 03, 2022
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April 14, 2022
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December 11, 2020
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December 29, 2019
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