Island Hopping in Gloucester

10 boats available

The best out of 10 deals in Gloucester - enter dates to check availability

Top Island Hopping in Gloucester

Island Hopping in Gloucester

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Gloucester

5.0
/5
Based on 124 reviews by boaters

What boaters said about Island Hopping

  • 5.0
    /5
    (3 Hour Sunset Sail with a meal.)

    Awesome experience

    Captain Rick and Deb were wonderful hosts aboard the Artemis. It was a lovely day of sailing paired with a delicious lunch. Couldn’t have asked for a better experience!
    Amy A.
    Amy A.
    Reviewed on Sep 21, 2026
  • 5.0
    /5
    (4 hour sailing trip for Pat B)

    Amazing Experience!!!

    The family and I had an amazing time on Artemis sailing with Captain Rick and his wife Deb. What an amazing experience to sail on such a beautiful yacht and with such wonderful people. If you've never sailed or are an experienced sailor, you will truly enjoy this great experience and discover Gloucester and the surrounding area. This sailing yacht is super stable, fast and fun. Make new friends, new experiences and amazing memories to last a lifetime! Sail Artemis!
    Patrixk B.
    Patrixk B.
    Reviewed on Sep 1, 2025
  • 5.0
    /5
    (5 Hour Trip – Whale Watching (AM))

    Wonderful experience!

    We went on a 4 hour whale watching trip with captain Matt and it was wonderful. The whales were hiding from us that day but captain Matt made sure we had a great time nonetheless! We had 3 kids with us and we stoped several time to catch fish, saw dozens of sea lions and fed them! The boat was very comfortable with seating out side and inside out of the wind and sun. 10/10 would recommend and do again. Thank you captain Matt
    Deanna S.
    Deanna S.
    Reviewed on Jun 11, 2025