Charter Packages
Three Ways to Sail Our Passion
Every charter is fully private and built around your group — your pace, your ports, your day on Vineyard Sound. Two USCG-licensed captains, up to six guests, no strangers aboard.
Package One
Sunset Sail
No two sunsets are alike, and that is a large part of why guests come back. The sky is nature’s canvas, and there are few better places to watch it repaint itself than the deck of a sailboat as one day closes and the evening opens.
Exciting, relaxing, or romantic — tell us which and we will shape the sail around it.
- Three Hours
- Up to Six Guests
- Golden Hour Departure
Package Two
Half Day Sail
Everything the full day offers, condensed. We pick a handful of the sights you most want to see and build four hours around them — ideal when the calendar will not surrender a whole day.
Departures are typically 9:00am or 1:00pm.
- Four Hours
- 9am or 1pm Start
- Choice of Sights
Package Three
Full Day Sail
You came this far for an island surrounded by water. Leave the land behind for a day and see Martha’s Vineyard the way it was first seen — from the water, with stops in ports that most visitors never reach by car.
- Ports & Sights We Can Work In
- Elegant Edgartown
- State Beach (of JAWS fame)
- The historic Inkwell Beach
- Cottage City, Oak Bluffs
- East Chop & West Chop lights
- Vineyard Haven Harbor
- Sheltered Lagoon Pond
- Lake Tashmoo
- The cliffs of Makonikey
- Lambert’s Cove Beach
- Menemsha fishing village
- Gay Head Cliffs & Light
Between legs we can anchor for a picnic, grill off the stern, swim, or go ashore for the best seafood each port has to offer. We know these waters, and we build the day around your tastes, the weather, the tides, and the light.
- Full Day
- Multiple Ports of Call
- Swim & Shore Stops
Why Sail With Us
There Is Nothing Cookie Cutter About Us
From our life experiences to the charters we run, we are unusual captains, and that carries into everything we do. No two charters are the same. Every decision is made around the client and their guests.
We handle the planning in advance so that all you have to do is step aboard and enjoy the sail.
Let’s Build Your Day on the Water
Tell us your dates and what you would like to see. Captain Mason or Captain Lynne will take it from there.