Find the best boat rentals near Gloucester, Massachusetts.

Average of 42 reviews in this area.
13 listings

Find top rated boat rentals in Gloucester, Massachusetts.

Gloucester, Massachusetts is a great place to rent a boat. You can rent or charter a small motorboat, sailboat, houseboat, 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.

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GetMyBoat customer reviews for boat rentals in Gloucester.

  1. SS
    Scott
    Charter 50ft "Frayed Knot" Cruising Monohull In Manchester-by-the-Sea, Massachusetts

    Our whole group would just like to send a huge thank you to Captain Claude and Judy for hosting us on the Frayed Knot for a spectacular afternoon of sailing! Both Claude and Judy could not have been more kind and accommodating for our large family sailing excursion. The boat is absolutely gorgeous, spacious, and comfortable. Our hosts provided great amenities for our sail, were so wonderful with our 2 small children, who could not stop talking about how fun the sail was -- "best sail ever!" If you are looking for a spectacular, comfortable, educational, and above all, memorable sailing experience for your family or larger group, we highly recommend the Frayed Knot! We look forward to future family sails with Claude and Judy.

  2. ML
    Molly
    Sailing Charters On 36ft Sailboat In Winthrop, Massachusetts Listed Marblehead but traveling to Boston, you will be able to Book from both Locations

    I would definitely recommend Captain Allan and Boat Emma Rose to my other friends. This was such a great experience and we had so much fun on sea. Captain Allan is very experienced and friendly, we also steered the boat a while on the sea. The boat is clean and nice.

  3. LT
    Linda
    Cruising Monohull Rental in Marblehead

    We had an amazing time. The winds were high, the waves were great and I even got to sail. It was both relaxing and exhilarating. Captain Allan has lots of great stories. He is a master of sailing!! Strongly recommend!!

  4. KB
    Karen
    65ft "Macgregor" Independence Sailboat Charter in Salem, Massachusetts

    We had a fantastic afternoon of summer sailing on the Independence! The ship is beautiful and Captain Lloyd and his first mate were wonderful hosts who made the day truly memorable for my family and our friends. Logistics and coordination were also a breeze 😁.

  5. AJ
    Alina
    Sailing Charters On 36ft Sailboat In Winthrop, Massachusetts Listed Marblehead but traveling to Boston, you will be able to Book from both Locations

    Allan was great! Very personable, with plenty of knowledge and life experience in the area. We had the best time celebrating a friend's birthday doing something you don't get to do every day, and it's a great experience if you don't get out on the water often! Highly recommend.

  6. JT
    Jessica
    Enjoy Fishing In Gloucester, Massachusetts With Captain Dana

    My husband and I had a fabulous day out at sea with Captain Dana! Dana is super knowledgeable and full of fun facts about Gloucester and the surrounding areas. For first time fishers, he was very patient with us and taught us everything we needed to know - and we ended up catching over a dozen mackerel for bait and 4 nice sized striped bass. On top of that, Dana was authentically New England and just the nicest guy. A great experience and we hope to do it again soon!