A solid border means we have called them; a dashed border means we found them and read their site, but have not called. Every price below is the operator’s own, as published on their site when we checked, and it can change: call before you plan around it.
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
Menemsha Blues ChartersMenemsha (Chilmark)
“Mary Sea” with Capt. Jonathan Boyd. Half and full days, and they clean what you keep.
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
MV SportfishingChilmark
27ft Shamrock center console out of Menemsha and around the Sound.
6 guests
no site we could find
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
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
Great Harbour Sport FishingEdgartown
“CayLee”, a 26ft Fortier. Nantucket Sound and Wasque Shoals.
6 guests
no site we could find
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
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
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
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
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)
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
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
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
Fishsticks ChartersVineyard Haven (Tisbury)
26ft Jones Brothers Cape Fisherman. Light tackle and fly, four to eight hours.
6 guests
Done Deal ChartersLake Tashmoo, Vineyard Haven (Tisbury)
Custom sportfisher that will pick you up from most island landings. Quarter, half and full days. We found no working website for them: the domain they used now points somewhere unrelated.
6 guests
no website
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
Beamish ChartersMartha's Vineyard
35ft Henriques Maine Coaster. Fishing, but also diving, sightseeing and picnic runs.
6 guests