The Black Dog Tall Ships are a timeless favorite. Their wood-hulled tall ships ply the waters of the Vineyard Sound on daily cruises. For information and to book tickets on a cruise, visit them at their website, theblackdogtallships.com
In Edgartown, Mad Max Sailing Adventures offers afternoon and evening cruises through Edgartown’s outer harbor as well as private charter offerings.
Sea Witch Sailing Charters offers day sails and charters around the island tailored to you.
Magic Carpet is a classic Sparkman & Stephens 56′ wooden yawl and a stunning sight to behold cruising around Edgartown Harbor. With a variety of cruises and charters offered, Magic Carpet is a local favorite.
Cat Boat Charters is another iconic sight in Edgartown Harbor. Enjoy customized private sailing and charters with Cat Boat and their crew aboard their beautifully restored Cape Cod Cat Boat.