Private charter or a seat on a shared cruise: it mostly comes down to how many of you there are and what you want to spend, and past about six people the choice makes itself.
We have called thirteen operators still running charters off this island, and know of more, from a restored 1927 catboat to a 53-foot Hatteras motor yacht. What follows compares private and group trips using MV prices and capacities, and says which kind suits which group.
What private charters and per-seat group cruises cost
Money usually decides it, so start there. Private charter prices on Martha's Vineyard depend on the boat, the length of the trip and the season. These are the figures for 2025–2026.
For private sailing charters, Sail The Vineyard takes a private two-hour sunset sail for $725 (up to six guests), while Martha’s Vineyard Charter Co. runs Our Passion, a 42-foot Pearson ketch out of Vineyard Haven, on a three-hour sunset sail for $825. Witch of Endor Sailing Charters sails Dulcinea, a 42-foot cutter, from Vineyard Haven with Capt. Pascal: $600 for two hours, $900 for a half day and $1,500 for a full day, with longer runs to other harbors around the Cape and Islands. Under power, Nauti Girl Excursions takes a double-decker pontoon out of Edgartown for $500 on a two-hour harbor cruise and $1,100 for four hours.
At the big end there is a gap this year. Mad Max Marina’s 49-passenger catamaran, the island’s largest charter boat, is closed for 2026 while a bigger boat is built; their site says it returns in 2027 or 2028. Until then, a big group means several smaller boats, or seats on a public sail.
Group and public cruises charge per person, so they cost much less up front. The Black Dog Tall Ships runs three-hour public sails on the Schooner Alabama for $100 per adult and $60 per child (ages 4–12). Sail The Vineyard offers public sunset sails at $200 per person (six maximum, 21 and over).
Split six ways, the $725 private sunset sail comes to about $121 per person. The Black Dog at $100 per person for three hours is slightly cheaper, but you share the boat with other guests. Four friends on the private sail pay about $181 each and get the boat, the captain, the music and the route to themselves. The fuller the boat, the smaller the per-person difference.
Group cruises save the most for one or two people. Two people on a $725 private sail pay about $360 each; on a $100 group sail they pay $100 each.
What a private charter gets you
The biggest difference is the route. On a private charter you plan it with your captain: anchor off Chappaquiddick for a swim, swing by the Aquinnah Cliffs, or run past the Elizabeth Islands toward Cuttyhunk. The captain adjusts for your interests, the weather and what the water is doing that day. Group cruises follow a fixed route with no deviation.
Most MV private charters are BYOB. Nauti Girl Excursions stocks coolers with ice, Martha’s Vineyard Oceansports supplies ice and coolers, and Catboat Charters includes drinking water and welcomes guests to bring food and drink. Witch of Endor includes water and sparkling water, and hors d’oeuvres on sails of three hours or more.
Then there is the USCG six-passenger limit. Most small charter boats on Martha's Vineyard operate under a USCG "six-pack" license, which means a maximum of six paying passengers. If your group is larger, you need either more boats or an inspected vessel. This year, with Mad Max closed and Plan Sea’s new boat limited to six, that mostly means more boats, the MV Skipper for a fishing party of up to 40, or the Black Dog’s schooner Alabama.
Amenities vary by boat, so ask: a bathroom on board matters more on a three-hour trip than people expect. Sailing Martha’s Vineyard in Menemsha runs everything from one-hour sails to overnights, and its site says the rate drops the further ahead you book and the more often you come back.
For something simpler, Island Time Charters (Captain JoJo Wild) runs a 26-foot pontoon on two-hour sunset and sightseeing cruises and will pick up in Oak Bluffs. Like most boats here it carries six paying guests at most, so a group of twelve is two boats, not one. It is not a fast sailboat, but you get your own captain, your own group and an easy afternoon.
When a group cruise makes more sense
Solo travelers and couples get the most out of group cruises: two to three hours on the water with an experienced crew, for a fraction of what a private charter costs. On the Black Dog's Schooner Alabama, a tall ship, passengers help raise the sails, which is hard to do on a small private boat.
First-time visitors who aren't sure what they want can let a group cruise make the decisions. The route is set, the crew handles everything, and you don't need to think about what to bring or where to go. It is a cheap way to find out whether you want a longer private charter later in the trip.
Families with young children sometimes prefer group cruises because the trip is short (two to three hours) and other people aboard keep kids busy. MV Pirates runs pirate-themed cruises for younger passengers from Oak Bluffs, with treasure hunts and costumes.
On a group cruise you don't control the pace, the route or the playlist, and you can't ask the captain to stay longer somewhere you like. On a busy summer evening, a boat with forty-odd strangers aboard feels like a floating party, which might be exactly what you want, or exactly what you don't.
Which kind of trip suits which group
Couples are best served by a private sail. A two-hour sunset sail on a classic catboat or sloop, with a bottle of wine and a cheese board, is a good MV date night, and Sail The Vineyard’s $725 private sunset sail is priced for exactly this.
Families of 4–6 fit a six-pack charter. Catboat Charters' restored 1927 catboat is steady and gentle even in wind, which helps if you have kids or anyone prone to motion sickness. Island Girl Excursions builds each trip around the group: beach stops, swimming, the Elizabeths. They run one boat, Bluebird, a 27-foot Albemarle, and Capt. Eamonn Solway is a licensed master and a paramedic, which is good to know if you are bringing small children.
Fishing groups choose between a party boat and a private charter. The MV Skipper party boat in Oak Bluffs runs public fishing trips at $100 per person with all gear and licenses included, which suits casual anglers. Serious fishermen book private charters with operators like North Shore Charters out of Menemsha ($850 for a half day inshore, up to six) or High Tide Charters in Edgartown ($550 for a half day on trips through October 31, 2026, as published on its site). Our Martha's Vineyard fishing guide has the details.
Corporate events and large celebrations need the bigger boats. The MV Skipper takes private charters for up to 40, with catering by request; On The Boat Charters in Oak Bluffs says its 38-foot Evans is Coast Guard certified for 12; and the Black Dog’s schooner Alabama sails from Vineyard Haven. Mad Max’s 49-passenger catamaran, the usual answer, is closed for 2026.
For wedding parties and bachelorettes, Sail The Vineyard lists weddings and vow renewals among its sails, and Steady As She Goes Charters lists bachelorette parties among the occasions it sails for. For a ceremony with more than six guests, see our wedding guide.
Deposits, cancellations and timing
Martha's Vineyard charter season runs roughly May through October, with most of the demand in July and August. Booking ahead matters more here than in most places, because the island has only so many boats.
Sunset slots on summer weekends go first, so for July and August, ask as soon as you know your dates. Shoulder-season trips (May, June, September, October) give you more choice of day. Ask whether the same trip costs less on a Tuesday or in September.
Deposits vary by operator. Island Girl Excursions, for example, takes a 20% deposit and charges the balance 72 hours before the trip. Ask what yours takes, and when the balance is due.
Read the cancellation policy before you pay. When the captain calls a trip off for weather, operators generally refund or reschedule. If you cancel, the rules are tighter: Catboat Charters refunds in full with 96 hours’ notice and gives store credit at 48–95 hours, and Island Girl Excursions cancels free of charge up to 72 hours before. As a general rule, assume you’ll lose your money if you cancel within two or three days of the trip.
Tip the captain and crew, as you would on any guided trip. The usual tip is 15–20% of the charter cost, and listed prices don’t include it.
How to decide
It comes down to whether you care more about control or about cost per person. A private charter gives you the boat, the captain and the say over where it goes. A group cruise costs less and can put you on a boat you might not otherwise get aboard.
For most groups of four to six, the per-person cost of a private charter comes close to a group cruise. For couples and solo travelers on a budget, a group cruise is good value without paying for the whole boat.
The operators we have called are on the list, with their phone numbers. Call them directly; nobody books through us.