Harbor Cruises & Island Adventures
Edgartown, Martha’s Vineyard
Elevate your Island Vacation with our Cruising Experiences
Captain Jack offers an exclusive cruising experience around Edgartown and Chappaquiddick aboard a timeless, New England–built vessel, accommodating up to six guests. Specializing in cocktail cruises and adventure excursions, guests can enjoy sightseeing coastal mansions with their libation of choice, then explore exclusive beaches and swim spots on Chappy.
What Sets Us Apart
Experience the ultimate in luxury and adventure with our custom charter services.
A Class of Our Own
Crafted in New England for local waters, our Roth Bilt center console features a blue hull, elegant wood accents, and Ralph Lauren–inspired cushions. She seamlessly combines comfort, timeless beauty, and exceptional maneuverability.
Experienced & Local Captain
Capt. Jack brings 30 years of experience and indepth knowledge of Martha’s Vineyard, with much of that time spent exploring her local waterways.
Unparalleled Experiences
From sunset cruises to swimming & beach excursions, casual outings or special occasions, your perfect day on the water begins here
Attention to Detail
We ensure you’re all set for a fun-filled outing, with a cooler, speaker, cups, and blankets provided on board. BYOB!
From the Logbook
Captain Jack was the best! So nice and funny, my boyfriend Joe and I had a great time and felt like we were with one of our friends. First time in Martha’s Vineyard and he made us feel so welcome. He went above and beyond and even gave us recommendations of where we should go next! Definitely recommend Chappy Charters!
Thanks Chappy Charters for a great cruise today!
If you’re looking for an outing on Edgartown Harbor, Jack is your guy
Thank you Chappy Charters for getting me to the Catboat Parade on time!
Captain Jack is the BEST!!
Jack was a great host. He knew who the owners were of the huge houses we passed and made sure we were getting the most out of our tour