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A charter boat's wake at dusk off Martha's Vineyard
The Actual List

Who runs boat charters on Martha’s Vineyard

Everyone we have called and checked, and then everyone else we know is out there. Call them yourself; there is nobody in between. Operators pay us nothing, and we add nothing to their price. Where a booking site pays us a commission, we say so on that page.

Read this first. We have no arrangement with anybody on this page. These are independent businesses, listed because they exist and because being told “contact us and we’ll connect you” when you could just phone them is a waste of your afternoon.

Almost every boat here takes six passengers maximum. That is a federal Coast Guard limit on boats the Coast Guard has not inspected, and it applies however big the boat looks. The few inspected boats below can take more, and say so; the rest cannot, at any price. For a group of ten, the answer is two boats leaving together, or one of the inspected boats: groups of seven or more. Fishing? The same operators are sorted by harbor here.

Details change: boats get sold, captains retire, rates move. Everything here was accurate when we last checked, but the operator’s own site is the authority. If you find something wrong, tell us and we’ll fix it.

Island Girl ExcursionsVineyard Haven (Tisbury)
“Bluebird”, a 27ft Albemarle, with Capt. Eamonn Solway: USCG master and Massachusetts paramedic. Sunsets, Aquinnah, the Elizabeths. Leaves from the Owen Park dock; pickups elsewhere cost extra. One boat, so seven people is two operators.
6 guests
Their site →(774) 563-8323
Martha's Vineyard Charter Co.Vineyard Haven (Tisbury)
“Our Passion”, a 42ft Pearson ketch. Capt. Mason and Capt. Lynne, both USCG 100T. Leaves from Vineyard Haven, Oak Bluffs or Lake Tashmoo.
6 guests
Their site →(508) 456-7245
Witch of Endor SailingVineyard Haven (Tisbury)
“Dulcinea”, a 42ft cutter-rigged double-ender, with Capt. Pascal Albanese. Morning, afternoon and sunset sails; for more than six, he can arrange a sister ship.
6 guests
Their site →(508) 685-1212
Sea Witch Sailing ChartersVineyard Haven (Tisbury)
58ft Pearson ketch with Capt. John. Two, four and eight-hour sails, mid-June to mid-September. Winters in St Thomas.
6 guests
(508) 650-0466
Sail The VineyardVineyard Haven (Tisbury)
“Phoenix”, a 44ft sloop, with Capt. Wendy Lea: USCG Master Mariner and the only ASA-certified instructor on the island. Memorial Day to the end of September.
6 guests
Their site →(508) 493-8767
Catboat ChartersEdgartown
Restored 1927 Cape Cod catboat, 30ft. Private sails.
6 guests
Their site →(508) 524-6903
Island Sailing ToursVineyard Haven (Tisbury)
“Tandemeer”, a restored 60ft ketch. Two to ten hours, day sails and sunsets. Launch out from Black Dog Wharf.
6 guests
Their site →(203) 246-1369
Nauti Girl ExcursionsEdgartown
“Feelin’ Nauti”, a 24ft double-decker pontoon, with Capt. Angie Fisher, a 15th-generation islander. Harbor rides, sunsets and six-hour beach days.
6 guests
Their site →(508) 939-1421
Alewife ChartersEdgartown
53ft Hatteras motor yacht. Custom cruises.
6 guests
MV Leisure ChartersMartha's Vineyard
Capt. Ed sold “Island Time” after 25 seasons. He now takes couples or single guests, by inquiry, on a smaller boat, and the trips are naturist: Moshup Beach and the Aquinnah cliffs.
2 guests
Their site →(508) 696-5252
Plan Sea Adventure ChartersEdgartown + Oak Bluffs
Private cruises from the Vineyard or from Falmouth, Friday to Monday, on 48 hours’ notice. Their site says the new boat is limited to six; older pages still describe the 18-passenger inspected boat, so ask which one you’d be on.
6 guests
Their site →(508) 687-2003
MV SkipperUSCG inspectedOak Bluffs
“Skipper”, a party fishing boat run by Capt. John Potter, fishing since 1987, and inspected by the Coast Guard every year. Daily trips at $100 a person, licenses and bait included, as published on their site (last changed August 2025): call to confirm. Private fishing and sunset charters for groups of up to 40.
40 guests
Their site →(508) 693-1238
Boylermaker ChartersOak Bluffs
Fly fishing and light tackle with Capt. Jaime Boyle, on a 24ft Silverhawk center console or an 18ft Chittum flats skiff. Half and full days, May through November. Gear and flies provided; bring your own fishing license. Checked on their site Oct 2, 2026.
4 anglers (2 on the skiff)
Their site →(508) 922-1749
Found, Not Called

Others we know are out there

The list above is everyone we have actually spoken to. These we have not: we found them, read their pages, and confirmed the sites are live, but we have not called the number or checked a license. They are here because leaving them off would have made the list above look more complete than it is.

Treat them exactly as you would a name off a search: worth a call, worth asking what the boat is and how many it takes. If you go out with one, tell us how it went and we will move them up.

Tomahawk ChartersMenemsha (Chilmark)
“Tomahawk 3”, a 35ft Carolina Classic, with Capt. Buddy Vanderhoop, of the Wampanoag Tribe of Aquinnah. Half day inshore $800 for 4.5 hours plus a $100 fuel surcharge; full day $1,600; offshore and canyon trips priced on their site. Checked on their site Oct 2, 2026.
6 guests
Their site →(508) 645-3201
Menemsha Blues ChartersMenemsha (Chilmark)
“Mary Sea” with Capt. Jonathan Boyd. Half and full days, and they clean what you keep.
6 guests
Local Tide ChartersMartha's Vineyard
A 32ft Regulator for the shoals and a 17ft Yellowfin skiff for sight-fishing the flats. Fly and light tackle.
6 guests
Fishsticks ChartersVineyard Haven (Tisbury)
26ft Jones Brothers Cape Fisherman. Light tackle and fly, four to eight hours.
6 guests
North Shore ChartersMenemsha (Chilmark)
Capt. Scott McDowell on “Lauren C”, a 35ft custom Duffy. Bass and blues inshore; tuna, sharks and marlin offshore. $850 half day, $1,650 full day, May through October. Checked on their site Oct 2, 2026.
6 guests
High Tide ChartersEdgartown
Capt. Russ Lawrence on “Mooncusser”, a 23ft Sailfish center console, from Dock St. Bass, blues, bonito, albies, fluke and sea bass, light tackle or fly. For trips July 1 to Oct 31, 2026: $550 half day, $800 for six hours, $1,050 full day. Checked on their site Oct 2, 2026.
6 guests
Their site →(508) 415-1540
Beamish ChartersMartha's Vineyard
35ft Henriques Maine Coaster. Fishing, but also diving, sightseeing and picnic runs.
6 guests
Captain Clarke ChartersMenemsha (Chilmark)
Capt. Jennifer Clarke on “Femme Fatale”, a Yellowfin center console at the Chilmark charter dock. Inshore $750 half day, $1,500 full day (six max); offshore day $2,000 (five max). Call or text. Checked on their site Oct 2, 2026.
6 guests
Their site →(508) 776-7286
Tenacious ChartersEdgartown
Capt. Eddie Smith on “Tenacious”, a 34ft South Shore, from 1 Dock St. Inshore bass, blues, sea bass, fluke and bonito; half and full days. Prices not published. Checked on their site Oct 2, 2026.
6 guests
Their site →(508) 274-1660
Red Moon ChartersEdgartown
Capt. Cooper Fersen on “Red Moon”, a 25ft Parker, fly and light tackle. Usually leaves Edgartown; trailers to Menemsha and Vineyard Haven. $750 half day (4 hours), $1,200 full day (8 hours). Checked on their site Oct 2, 2026.
4 anglers
Their site →(802) 338-7978
Martha’s Vineyard OutfittersEdgartown
Capt. Brice Contessa, fly and light tackle from a 20ft NorthCoast center console. Six-hour trips, catch and release only, early May to mid-November. Rates not published on the pages we could open. Checked on their site Oct 2, 2026.
2 anglers
Kismet OutfittersEdgartown
Fly shop at 204 Upper Main St with guides. Boat (center console or flats skiff) $600 half day, $1,100 full day; from the beach $475 half day, $800 full day. Checked on their site Oct 2, 2026.
Fly fishing
Smokin Eel ChartersOak Bluffs
Capt. Tom on a 32ft Century from the Oak Bluffs Marina. Inshore half day (4 hours) and full day (up to 8 hours). Price upon request. Checked on their site Oct 2, 2026.
Ask
Their site →(508) 662-7939
Silent Witness ChartersOak Bluffs
A 36ft Yellowfin at Slip 35, Oak Bluffs Harbor. Inshore and offshore, May to October; half day inshore (4 hours) $1,500, with offshore and canyon trips priced on their site. Checked on their site Oct 2, 2026.
Ask
Their site →(786) 559-5006
Cheap Therapy ChartersOak Bluffs
Capt. Kyle on “Cheap Therapy”, a 28ft Bertram (1977, restored 2022). Fishing $750 for 3 hours, $950 for 4, $1,350 for 6; also sunset and island cruises. BYOB. Checked on their site Oct 2, 2026.
6 guests
On The Boat ChartersUSCG certifiedOak Bluffs
A 38ft Evans, owner and captain Donny Brice. Their site says the boat is certified by the Coast Guard for up to 12 passengers plus 2 crew. Cruises, fishing and water taxi, priced by the hour: 2 hours $1,500, 3 hours $1,850, 4 hours $2,450. Checked on their site Oct 2, 2026.
12 guests
Their site →(917) 699-3306
Steady As She Goes ChartersVineyard Haven (Tisbury)
“Dream Catcher”, a catamaran, with Capt. Gary Staples. Three and five-hour sails.
Ask
Martha’s Vineyard OceansportsOak Bluffs
Private 90-minute sunset cruise from $575; waterski, wakeboard and tubing charters at $385 an hour with a captain, up to six. Also parasailing and jet skis. 12 Circuit Ave Extension.
6 guests
Their site →(508) 693-8476
The Black Dog Tall ShipsVineyard Haven (Tisbury)
The schooner Alabama. Three-hour day and sunset sails from the Black Dog Wharf, sold by the ticket: $100 adults, $60 ages 4–12. Fireworks sails, and private charters for weddings and events.
Shared sails
Their site →(508) 693-1699
If Nobody Answers

Email first, and try a weekday

July and August Saturdays on the good boats are usually gone by about mid-June. Several of these captains run the boat themselves, so in season they are out on the water when you call. Email usually beats calling, and a weekday usually beats a weekend.

If you have tried the list and come up empty, write to us with your date and headcount. We will go back through the list with your date in mind. We can’t conjure a boat, and if we can’t find one we will tell you that.

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