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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$200-$815
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$495
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$500
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$85-$650
Kayaks
Who says you need a motor to have fun on the water?
$10-$470
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$175-$650
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$275
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$150
Canoes
A classic option for leisurely paddling
$10
TI
Tony
Sunset 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.
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 !!
JC
Jennifer
Cal 36 Sailboat Rental in Marblehead, Massachusetts
We had a wonderful experience with Captain Allan and his beautiful sailboat! He was very nice and explained things to us, let us help him with the rigging and sailing, let us take pics and hang out all over the boat, let us play our music and bring our own cooler. We had fantastic weather and saw how beautiful Marblehead was! Would highly recommend!
OM
Olivia
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing with Captain Al was a wonderful experience. The entire Marblehead area was so beautiful to see from the water and Captain Al was a very informative guide. The sailboat, Emma Rose, was so picturesque, it really felt like we were in a movie. This is certainly an experience we will remember for a lifetime.
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Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
August 01, 2023
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