Martha’s Vineyard Charter Company
Private Sailing Charters Aboard Our Passion
Explore the Vineyard the way it was first explored — under sail, with two USCG-licensed captains and no one aboard but your own group. Departing Oak Bluffs, Vineyard Haven, or Lake Tashmoo.
A proper bluewater ketch — not a crowded tour boat.
Our Passion is a 42-foot Pearson ketch, owned and sailed by the two captains who maintain her. When you book, the whole boat is yours — just your group, up to six guests, and the water.
Weather and conditions permitting, we’ll typically drop anchor somewhere quiet and shut the engine down. There’s a swim platform on the stern, a ladder, and a hot and cold fresh water shower for afterward. Bring your suit.
Our Vessel
Meet Our Passion
A 42-foot ketch that has sailed from Maine to the Bahamas, and from Martha’s Vineyard to Ireland and back. She is more than equipped for a day on Vineyard Sound you will not forget.
What is better than one captain? Two. Captain Mason and Captain Lynne have sailed together for nine years — their first date was on a sailboat. Between them they hold 40 years of experience, US Coast Guard 100-Ton Master licenses, and lifeguard certification.
Meet the CaptainsCharter Packages
Sunset Sail
Golden hour on the water aboard your own private sailboat. Exciting, relaxing, or romantic — you tell us which.
$825Three Hours
Half Day Sail
Focus on the few places you most want to see, built into four hours. Departures at 9:00am or 1:00pm.
$1,100Four Hours
Full Day Sail
Leave the land behind. Edgartown, Menemsha, the Gay Head cliffs, swim stops and shore lunches — the whole island from the water.
$2,200The Whole IslandOver One Hundred Five-Star Reviews
From guests who sailed Vineyard Sound with Captain Mason and Captain Lynne.
“It was the best part of the weekend. It was a magical day. Highly, highly recommended!”
Alexis N.Brooklyn, NY
“The best boat tour we have ever been on. We have sailed in Hawaii, Laguna Beach and now Martha’s Vineyard, and felt the most hospitality here. Thank you both for such a great memory!”
Brandon M.Las Vegas, NV
“We visited MV for my birthday and chartered Captains Mason and Lynne’s sailboat. Beautiful landscapes, magnificent sunsets and great conversation. We couldn’t have had a better time!”
Telisha F.Philadelphia, PA
Martha’s Vineyard Sailing Charters Await You
Tell us your dates and what you would like to see.Captain Mason or Captain Lynne will take it from there.