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Find boat rentals at the best price near Gloucester, MA.

5.0(Average of 77 reviews in this area)
Get set to boat with the GetMyBoat Guide to Gloucester
7 listings
I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.
Sailing in Marblehead · 6 guests

I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

5.0
$135hour
Enjoy Fishing In Gloucester, Massachusetts With Captain Dana
Fishing in Gloucester · 4 guests

Enjoy Fishing In Gloucester, Massachusetts With Captain Dana

4.9
$119hour
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
$550hour
Sundeer 64’ Pilothouse Ketch in Gloucester MA and New England
Gloucester · 6 guests

Sundeer 64’ Pilothouse Ketch in Gloucester MA and New England

5.0
$175hour
Enjoy the water with friends and family with Sea Ray 310 Sundancer Motor Yacht in Danvers, Massachusetts
Events in Danvers · 6 guests

Enjoy the water with friends and family with Sea Ray 310 Sundancer Motor Yacht in Danvers, Massachusetts

New
$350hour
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
$225hour
Authentic 122ft Schooner Adventure - A National Historic Landmark
Sailing in Gloucester · 60 guests

Authentic 122ft Schooner Adventure - A National Historic Landmark

New
$1,000hour

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Gloucester Reviews

  1. OM
    Olivia
    I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

    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.

  2. Philip
    Philip
    I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

    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! 🤙☮️♥️

  3. Peter
    Peter
    I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

    This was a great charter, sailing around the islands about Marblehead and having great conversation about the area, sailing, and life in general. The charter started on time and the weather turned out to be great. Winds were off and on but we had some great heeling action. Totally recommend Captain Allan for a special afternoon charter!

  4. LM
    Laura
    I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

    Capt Al was excellent - the boat fit our party of 7 nicely! We enjoyed the sail and talking with him. Communication pre-sail was great. Unfortunately our sail was shortened by an hour because of foggy weather causing us to miss the first hour. Other than that, we were very happy. Hope to be back.

  5. Melissa
    Melissa
    I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

    Captain Allan was absolutely fantastic. The sail was beautiful and comfortable and he was extremely friendly, gives you background on the MA area you sail around and overall just a fantastic experience. Our sail with him was the highlight of our weekend. Highly recommend!

  6. NG
    Nicole
    I offer sailing charters on Cal 36 Sailboat. We sail around the islands of the Gold Coast of Boston’s north shore. I will come to Boston ,if I am available on your charter date.

    I booked this as a 10 year wedding anniversary gift for my husband. Captain Allan was extremely friendly, knowledgeable, and took us out on an unbelievable, unforgettable experience. I was thrilled with the whole thing - from inquiring about the trip, so when we came back on the dock. He was incredibly easy to work with, responsive, and when we got on board, he made us feel safe, and like we were old friends. If possible, we will absolutely do this again! Thank you for everything Captain Allan!

Boating Guide - Gloucester

Find top-rated boat rentals in Gloucester, Massachusetts.

Hoist the sails as Gloucester, MA is a great place to rent a sailboat. You can rent or charter a small motorboat, sailboat, or even a yacht. Take in the beautiful scenery and spend quality time with your friends and family while having the perfect day on the water. From birthday celebrations and bachelor or bachelorette parties to family vacations, Gloucester, Massachusetts is the perfect boat rental destination.

GetMyBoat has 7 listings for boating experiences in Gloucester with 77 reviews.

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