Charter Packages
Four 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.
“It never felt like a typical tourist excursion.”
— Patrick D., TripAdvisor
All of our charters can be customized to make yours perfect. Here are some suggested options:
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.
We do not turn for home at sunset. The light after the sun drops is often better than the sunset itself, and the sail back in the dark is worth the evening on its own.
Exciting, relaxing, or romantic — tell us which and we will shape the sail around it.
“So neat to be out on the water after the sun set. We never felt cramped and moving on the boat was very easy.”
— Dave M., TripAdvisor
- Three Hours
- Up to Six Guests
- Out Past Sunset
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.
There is time for a swim stop on a half day, and most groups take it. A stern swim platform and boarding ladder make getting in and out of the water easy, and there is a hot and cold fresh water shower on the stern for afterward.
Departures are typically 9:00am or 1:00pm.
“They even let us jump off the boat for a couple of refreshing swims.”
— Malika R., TripAdvisor
- Four Hours
- 9am or 1pm Start
- Swim Stop
Package Three
Five Hour Sail
The middle option, and often the right one. Four hours is enough to see the harbours close to home, but the eastern end of the island is a stretch. That extra hour is what makes Edgartown comfortable rather than rushed — time to round Edgartown Light, run down the Chappaquiddick shore, and still anchor for a swim before turning back.
Choose this one when the half day would leave you watching the clock and the full day is more than the schedule allows.
“We really loved the experience that included ample sailing and swimming time.”
— Kerry Kleisner, Google
- Five Hours
- Swim & Lunch Stop
- Reaches Edgartown
Package Four
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, swim, or go ashore for the best seafood each port has to offer. Cuttyhunk and the Elizabeth Islands are within reach on a full day, and on a good breeze it is the best sail we offer. We know these waters, and we build the day around your tastes, the weather, the tides, and the light.
“Sailing past the iconic Jaws Bridge between Edgartown and Oak Bluffs.”
— David Shamoon, Google
- Full Day
- Multiple Ports of Call
- Swim & Shore Stops
Special Occasions
Engagements, Anniversaries & Celebrations
Because every charter is booked privately for the whole boat, Our Passion suits the days that need to belong entirely to you. We are glad to work around a photographer’s timing, plan the route toward a particular view, or simply stay out of the way at the right moment.
Tell us what the day is for when you inquire and we will build it accordingly.
- Proposals
- Engagements
- Anniversaries
- Birthdays
- Family Reunions
- Photo Shoots
“Kind enough to allow us to book Our Passion for an engagement photo shoot.”
— Katelyn G., TripAdvisor
“They made my proposal sooooooo special!”
— Sheena Jennings, Google
“They helped us to surprise our dad who misses sailing on Cape Cod.”
— Megan Forrester, Google
At a Glance
Martha’s Vineyard Charter Facts
Everything about a private sailing charter aboard Our Passion, in one place.
- Vessel
- Our Passion, a 42-foot Pearson 422 ketch, rigged with genoa, mainsail, and mizzen and sailed in whatever combination the day’s wind calls for. A 58 hp Westerbeke diesel handles docking and fills in when the wind does not.
- Crew
- Capt. Mason and Capt. Lynne, the owner-operators, sail every charter themselves. Both hold U.S. Coast Guard 100-Ton Master licenses and lifeguard certification, with more than 40 years of combined sailing experience.
- Capacity
- Up to six guests per charter, plus two USCG-licensed captains. Every charter is fully private — you are never grouped with strangers.
- Departure Points
- Vineyard Haven, Lake Tashmoo, or Oak Bluffs. Alternate pickup points can sometimes be arranged by request.
- Charter Options
- Sunset Sail — 3 hours, from $825. Half Day Sail — 4 hours, 9:00am or 1:00pm departure, from $1,100. Five Hour Sail — from $1,375. Full Day Sail — from $2,200. Rates cover the whole boat, not per person. Gratuity is not included; 15 to 20 percent is customary for your two captains.
- Season
- Charters run May 15 through September 30. Dates outside that window are not available.
- Cruising Grounds
- Vineyard Sound and the Martha’s Vineyard coastline. Sunset sails stay close to home — East and West Chop lights, Oak Bluffs, Inkwell Beach, Lagoon Pond, and Lake Tashmoo. Half day sails add State Beach and Lambert’s Cove. Five hour sails reach Edgartown, Edgartown Light, and the Chappaquiddick shore. Menemsha, the Gay Head Cliffs, and Cuttyhunk are full day territory, since reaching the western end of the island takes five hours or more.
- Aboard
- Marine head (bathroom), refrigerator and freezer for guest use, and cushioned seating in the cockpit, bow, and stern. A stern swim platform and boarding ladder make getting into the water easy, and a hot and cold fresh water shower on the stern lets you rinse off afterward. Bottled water is provided.
- Food & Drink
- Guests bring their own food and beverages, including beer, wine, and cocktails. Alcohol is not provided. A refrigerator, freezer, and bottled water are aboard for your use.
- Not Permitted Aboard
- Deeply pigmented foods and drinks that permanently stain fiberglass and gelcoat — red wine, sangria, red juices, and berries among them. Marijuana and other controlled substances, prohibited under the federal law governing these waters. Smoking and vaping of any kind. Everything else you would bring for a day on the water is welcome; the FAQ has the full list.
- Swimming
- Permitted, at the Captain’s discretion based on conditions, traffic, and current. Swim and shore stops can be built into half day, five hour, and full day charters. A stern swim platform, boarding ladder, and fresh water stern shower are aboard.
- Who We Sail With
- Families, couples, and small groups of friends — including proposals and engagements, anniversaries and birthdays, multigenerational family trips, first-time sailors, and guests who simply want a quiet day on the water. Our Passion suits groups looking for a relaxed, private sail rather than a public party charter.
- Accessibility
- Boarding is by dock or by tender, and moving about the boat involves steps and uneven footing under way. Tell us about any mobility, medical, or sensory needs when you inquire and we will walk you through what boarding and the day would involve, so you can decide whether it is a good fit.
- Children & Dogs
- Children are welcome; U.S. Coast Guard–approved life jackets are carried in all sizes. Well-behaved dogs are welcome — tell us in advance either way. One guest: “We had the best afternoon with our family and dogs!” (McKenzie Duncan, Google)
- Payment
- A 50% deposit reserves your date; the balance is due four days before the charter. Bookings inside four days are paid in full at booking. Venmo and Zelle are free; major U.S. credit cards carry a 3.5% processing fee passed along at cost.
- Cancellation
- If the Captains cancel for unsafe weather, our guests receive a full refund. Cancelling 14 or more days ahead also brings a full refund. Inside 14 days, 50% of the charter fee is forfeited — for most bookings that is simply the deposit already on file, with nothing further owed. Charters booked inside four days are paid in full at the time of booking; if a guest cancels one, the fee is returned only if the Captains rebook that slot. Whenever the slot is rebooked, the forfeited amount comes back to our guest.
- Booking
- Call (508) 456-7245, email info@marthasvineyardchartercompany.com, or request a date online. We reply within 24 hours.
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.
“The crew absolutely knew what they were doing. We felt completely relaxed and safe.”
— Susan M., TripAdvisor
“They know the waters around Massachusetts like the back of their hand.”
— Robert H., TripAdvisor
“Booked on short notice and it was the highlight of a great MV vacation.”
— Tammi Cody, Google
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. Last-minute dates are worth asking about — they open more often than people expect.