Harbor Cruises & Island Adventures
Edgartown, Martha’s Vineyard
Elevate your Island Vacation with our Cruising Experiences
Capt. Jack offers an exclusive cruising experience around Edgartown and Chappaquiddick aboard a timeless New England built vessel suitable for couples, families, and friends. Enjoy sunset cruises, coastal mansion & lighthouse sightseeing, ‘Jaws’ bridge jumping, and scenic Cape Poge adventures. Accomodating up to 6 guests.
See 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 New England, our Roth Bilt center console combines comfort, timeless beauty, and maneuverability - allowing you to go where no other charter can
Experienced & Local Captain
Capt. Jack brings over 20 years of local knowledge & experience navigating the waterways around the Vineyard
Unparalleled Customer Service
From sunset cocktail cruises with friends to secluded swimming spots with the family - your perfect day on the water begins here
Attention to Detail
We maintain a high standard of cleanliness and make sure you’re all set for a fun-filled experience, with a cooler and speaker ready on board
What People Say About Us
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