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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
$150hour
Enjoy Fishing In Gloucester, Massachusetts With Captain Dana
Fishing in Gloucester · 4 guests

Enjoy Fishing In Gloucester, Massachusetts With Captain Dana

4.9
$119hour
Mainship 40ft Yacht with Captain in Newburyport
Events in Newburyport · 12 guests

Mainship 40ft Yacht with Captain in Newburyport

5.0
$300hour
Sail with us aboard ARTEMIS in Gloucester MA and New England
Sailing in Gloucester · 6 guests

Sail with us aboard ARTEMIS in Gloucester MA and New England

5.0
$250hour
Robalo R222 Center Console Rental in Newburyport, MA
Powerboats in Newburyport · 5 guests

Robalo R222 Center Console Rental in Newburyport, MA

New
$100hour
Private Charters on Classic 80' Schooner yacht in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Schooner yacht in Salem, Massachusetts

5.0
$498-$550hour
Water Ski/Tubing/Wakeboard with Driver/Instructor
Powerboats in Gloucester · 5 guests

Water Ski/Tubing/Wakeboard with Driver/Instructor

New
$145hour
Shark Fishing in Newburyport, Massachusetts
Fishing in Newburyport · 6 guests

Shark Fishing in Newburyport, Massachusetts

New
$124-$133hour
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-$225hour
Large Group Experience : Private Events  in Gloucester, Massachusetts
Events in Gloucester · 46 guests

Large Group Experience : Private Events in Gloucester, Massachusetts

New
$499-$699hour
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
$1,150-$1,300hour

Gloucester Reviews

  1. 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.

  2. 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.

  3. 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 !!

  4. 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!

  5. 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.

  6. Philip

    Philip

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    Captain Allen is an amazing captain great with kids and adults alike. Loved sailing with him and his stories were incredible. He taught me much about sailing the ship I feel I can almost sail myself with a small crew. Also fell in love with his 1967 sailboat I need one in my life! I could do this every day and I just might do that. He made our send off of out Father one of the best days we could have ever asked for. It really was the perfect day! Hope to see u soon onour next adventure. First m8 Phil out! 🤙☮️♥️