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Oak Bluffs Fishing Charters

The best out of 105 charter fishing deals in Oak Bluffs - enter dates to check availability

Oak Bluffs Fishing Charters

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Top Fishing Charters in Oak Bluffs

Oak Bluffs: 105 fishing charters available

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Listing image
Up to 30 people
CAPEJAWS FISHING CHARTERS
Mashpee (1 hr 27 min drive from Oak Bluffs)
CAPEJAWS CHARTERS — Land-Based Shark Fishing on Cape Cod Welcome to CapeJaws Charters, Cape Cod's premier land-based shark fishing experience.
trips from
HK $3,921
Listing image
26 ft
Up to 5 people
Fish Bandit Charters – Falmouth, MA
5.0
/5
(74 reviews)
Falmouth (1 hr 7 min drive from Oak Bluffs)
Fish Bandit specializes in introducing their clients to the wonderful angling opportunities in Massachusetts. Join Captain Skip Bandini aboard his fishing machine and see what Vineyard Sound fishing is all about. Capt.

"We had a great time on our fishing trip with Captain Skip the Fish Bandit." —⁠ Carl,
trips from
HK $5,098
Angler's Choice
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25 ft
Up to 6 people
Squid Row Charters
5.0
/5
(22 reviews)
Mashpee (1 hr 26 min drive from Oak Bluffs)
Squid Row Charters is a highly-rated fishing charter and boat tour company on Cape Cod, Massachusetts We offer two types of fishing trips: 2.5 hour and 4 hour trips. Our 2.

"We had a 4 hr trip starting at 7 am and Chris did not disappoint as our captain." —⁠ Mark,
trips from
HK $2,353
Listing image
27 ft
Up to 6 people
Vineyard Boat Charters with Capt. John Hobby
5.0
/5
(15 reviews)
Tisbury (12 min drive from Oak Bluffs)
Vineyard Boat Charters is a bottom fishing charter that focusses on a family fishing experience that no other charter on the island does.

"I can’t recommend Captain John enough!  He was incredibly patient and helpful, making sure everyone had a great time from start to finish." —⁠ Justin,
trips from
HK $3,529
Listing image
28 ft
Up to 6 people
Cape Fishing Charters
4.9
/5
(66 reviews)
Falmouth (1 hr 7 min drive from Oak Bluffs)
Make an adventure from your next trip to Cape Cod and go fishing with Cape Fishing Charters. Your guide for the day is Captain John, which allows you to benefit from years of local experience.

"Captain John was outstanding! He was personable, relatable, and especially helpful with the kids, patiently assisting them with baiting their hooks and casting their lines." —⁠ Sara,
trips from
HK $4,705
Listing image
35 ft
Up to 6 people
Mid-Cape Sportfishing
4.8
/5
(27 reviews)
Yarmouth (1 hr 57 min drive from Oak Bluffs)
Yarmouth has a fish with your name on it, so let Mid-Cape Sportfishing help you catch it! These waters are known for Striped Bass, Bluefish, Cod, Haddock, Black Seabass, Scup (Porgy), Bluefin Tuna, Bonito, Blue Shark, Squid, and more – with any luck

"Our captain was great! There were 5 of us, we all caught atleast 20 fish each." —⁠ Ray,
trips from
HK $5,490
Listing image
32 ft
Up to 6 people
Obsession Sportfishing - Marthas Vineyard
New
Oak Bluffs
There's a fish with your name on it in Falmouth and Obsession Sportfishing will help you catch it! Striped Bass, Bluefish (Tailor), Little Tunny (False Albacore), Black Seabass, and more could be biting, depending on the time of year.
trips from
HK $6,470
Angler's Choice
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25 ft
Up to 6 people
On The Edge Charters
5.0
/5
(73 reviews)
Fairhaven (1 hr 47 min drive from Oak Bluffs)
Lets embark on an Unforgettable Fishing Adventure i'll let our reviews speak for us!!! Join us for a thrilling day on the water, crafting unforgettable memories on the pristine waters of Massachusetts.

"we had a blast! Capt. Rick and his first mate Justin are awesome!" —⁠ Joan,
trips from
HK $5,098
Listing image
27 ft
Up to 4 people
Tiggertoo Charters
4.9
/5
(173 reviews)
Sandwich (22.0 miles from Oak Bluffs)
Tiggertoo Charters invites you for a day of exciting fishing in the waters of Cape Cod Bay.

"The captain (Bob Joyce) was great to work with. We had to modify our trip schedule several times due to weather and sea conditions." —⁠ John,
trips from
HK $3,921
Listing image
25 ft
Up to 5 people
Annie Bee Sportfishing 🐝
5.0
/5
(101 reviews)
Barnstable (22.0 miles from Oak Bluffs)
Looking to fish with an experienced Cape Cod fisherman? Then Annie Bee Sportfishing has a trip with your name on it! Your guide for the day is 3rd generation Captain Jarred Bolduc, offering 34years of sportfishing experience on Cape Cod Bay.

"This was my second trip with Captain Jarred and we had an amazing time!" —⁠ Evans,
trips from
HK $3,137

Top deep sea fishing trips in Oak Bluffs

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Top-rated family fishing trips in Oak Bluffs

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Half-day fishing trips in Oak Bluffs

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Frequently Asked Questions about Fishing Charters in Oak Bluffs

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Fishing in Oak Bluffs

Oak Bluffs sits on the northeastern edge of Martha's Vineyard, perfectly positioned between Vineyard Sound and Nantucket Sound—two productive fisheries that draw anglers from across New England. With quick access to sheltered waters and open stretches, Oak Bluffs fishing charters can tailor trips for first-timers and seasoned pros alike.

Inshore, expect classic Vineyard action. Striped Bass cruise the boulder fields, rips, and tide-swept points, while Bluefish slash through bait along the beaches and around the chops. Black Sea Bass, Scup (Porgy), and Fluke keep rods bending over reefs, shoals, and sandy drop-offs, offering variety and great eating opportunities when in season.

When the water warms, fast-moving pelagics light up the sounds. False Albacore and Bonito blitz bait near the surface, delivering sight-casting thrills on light tackle. Head a bit farther and you may find shots at larger game when conditions allow, with tuna and other offshore visitors appearing on the right temperature breaks.

Spring through fall is prime, with calm mornings, strong tidal movement, and migrating bait setting the stage for memorable outings. Local captains know how to work the rips, read the birds, and position you for success—whether you prefer topwater plugs, live bait, or fly. Book an Oak Bluffs fishing charter to tap into a rich, diverse fishery a short cruise from the harbor.

Oak Bluffs

Based on 31,116 reviews by FishingBooker anglers

Recent Catches in Oak Bluffs

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What anglers said about fishing in Oak Bluffs

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How did anglers rate fishing charters in Oak Bluffs?

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