Gloucester Boat Hire

Average of 27 reviews in this area.
4 listings

About Gloucester

Gloucester, Massachusetts is a historic town on Cape Ann. Visitors have been drawn to the coastal Atlantic seaport for more than 400 years.

The town is a working fishing community and one of the biggest events of the summer season is the annual St. Peter's Fiesta that honors the patron saint of fishermen. The Fiesta features carnivals, parades, and the blessing of the fleet. Visitors may charter a boat for deep-sea fishing trips or travel 12 miles out to sea to Stellwagen Bank, one of the top destinations worldwide to see the many species of whales that migrate to the region.

History buffs love visiting the lighthouses that date back to the 18th century. The two oldest are the twin lighthouses on Thatcher Island, which is accessed by boat.

Spend a day at the beach, but come early. Parking is available at Stage Fort Park, and trolley service is available to the beaches. Cressey's Beach and Half Moon Beach are at the park and overlook the harbour. Wingaersheek Beach is on the Annisquam River and Ipswich Bay and is popular with locals and visitors.

Gloucester, Massachusetts, United States is a favorite summer destination for the beaches, the arts, shopping and New England seafood.

Top destinations nearby

GetMyBoat customer reviews for Tours, Lessons, and Diving in Gloucester.

  1. LR
    Lynne
    Schooner rental in Salem for all types of events and private sails

    We had a fantastic sailing with Mike and his crew. We went on a two hour sailing as a team event. The schooner was beautiful, and everything was very well taken care of on the boat. The crew let us help raise the sails which was a lot of fun to be a part of. They kept up with helping us with drinks and snacks, all very reasonably priced too. The scenery was gorgeous – we couldn’t have asked for a better afternoon!

  2. MU
    Morgan
    I offer sailing charters on the Emma Rose , a Cal 36. 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.

    We had a great trip with Captain Allen. There wasn't a lot of wind, but he was working valiantly to catch any breeze that came our way. I also loved that he made it an interactive trip by allowing us to help out with various tasks. Captain Allen was knowledgeable, friendly and told great stories to make our trip memorable.

  3. NC
    Nicola
    I offer sailing charters on the Emma Rose , a Cal 36. 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 great! He told us some great stories and even explained the basics of sailing to us. We booked a 2 hour trip for our friend's birthday and had a lovely, relaxing time on the boat.

  4. AF
    Ali
    I offer sailing charters on the Emma Rose , a Cal 36. 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.

    Allan was great, the trip was outstanding, relaxing and smooth. Allan is very experienced, and engaging with everyone. Kids loved it. overall experience was awesome.

  5. HI
    Hakan
    I offer sailing charters on the Emma Rose , a Cal 36. 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.

    It was amazing first sailboat and sailing experience with Emma Rose boat and captain . Thank you so much for nice evening and sharing all your experiences and joy with us.

  6. ER
    Elana
    I offer sailing charters on the Emma Rose , a Cal 36. 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.

    Really fantastic experience!! Lots of fun and had a great time on the boat ! Would highly recommend Captain Allan