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

Average of 35 reviews in this area.
9 listings

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 customer reviews for boat rentals in Gloucester.

  1. 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.

  2. 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.

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

    We had such a wonderful time aboard the Emma Rose with Captain Allan! We took my father for his birthday, in May and had such a wonderful time! We were able to pack a picnic, and were able to get really hands on with the sailing, and learned so much! The trip was so relaxing and refreshing! My dad still talks about how wonderful that day was, and how much he learned! Captain Allan is great with communication before hand as well, and answered all our questions promptly! We had an amazing sail around the north shore and are looking forward to planning our next sail with Captain Allan! We would highly recommend!

  4. SS
    Scott
    Cruising Monohull Rental in Marblehead

    What a wonderful sail our family had with Captain Allan! Everything was perfect. Our sail started right on time, he provided great information on the boat, where we would be sailing and a lot of interesting details about the surrounding area. The kids had a great time and the joy they had steering the boat was amazing. They said it was the best day ever! Captain Allan was so great with them. We highly recommend a sail with Captain Allan and look forward to future sailing with him.

  5. SS
    Scott
    Charter 50ft

    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.

  6. CP
    Cristal
    Charter 50ft

    This was the highlight of our entire trip. Claude and his wife are extremely knowledgeable and amazing hosts. We got to see amazing structures and islands and even learned some interesting facts. We got to swim and enjoy the beautiful waters. Claude even let some of us drive the boat (with supervision of course.) To top it all off we even got some complimentary goodies including some coozys and pens! Their hospitality was so incredible that it felt like we all knew each other for a long time. I will absolutely be booking the Frayed Knot next time we make this trip. Thank you again Claude and Judy!