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Oak Bluffs Fishing Charters

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The best out of 101 charter fishing deals in Oak Bluffs - enter dates to check availability

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Top Fishing Charters in Oak Bluffs

Oak Bluffs: 101 fishing charters available

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    Vineyard Boat Charters with Capt. John Hobby

    Tisbury: 12 min drive from Oak Bluffs

    Vineyard Boat Charters is a bottom fishing charter that focuses on a family fishing experience that no other charter on the island does.

    "We are more than thrilled with our experience with Captain John Hobby and Vineyard Boat Charters!" —⁠ Jamila,

    Trips from:
    US $450
  • Angler's Choice

    Squid Row Charters

    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 Our two most popular types of fishing trips: 2.5 hour and 4 hour trips. Our 2.

    "Awesome first-time experience booking a fishing charter! We are a family of four doing this for the first time including two under 10 y.o" —⁠ Paul,

    Trips from:
    US $375
  • Angler's Choice

    Mid-Cape Sportfishing

    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

    "The captain did his job perfectly. We were all beginners and we all felt like we were prepared during the tuna trip." —⁠ Alexander,

    Trips from:
    US $700
  • Angler's Choice

    Cape Fishing Charters

    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:
    US $600
  • Angler's Choice

    Annie Bee Sportfishing 🐝

    Barnstable: 1 hr 48 min drive 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 36 years of sportfishing experience on Cape Cod Bay.

    "I can explain how happy I am that I picked the Annie Bee for my wifes and I to get out on a charter while in town for our hunnymoon." —⁠ Michael,

    Trips from:
    US $450

    Fish Bandit Charters – Falmouth, MA

    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.

    "Captain Skip and his first mate Don were fantastic. Very professional and experienced, we caught fish in the first couple minutes of trolling and they kept biting throughout the whole trip." —⁠ Nico,

    Trips from:
    US $650

    On The Edge Charters

    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.

    "Every summer our family makes the trip to New England, and one tradition we never skip is getting out on the water." —⁠ Frederick,

    Trips from:
    US $700
  • Angler's Choice

    Showtime Sportfishing

    Dennis: 2 hr 6 min drive from Oak Bluffs

    Embark on an unforgettable fishing expedition aboard the vessel “Showtime,” a pristine 26-foot Regulator.

    "We’ve made this fishing trip an annual tradition, and this year’s trip with my son was especially meaningful as we did it before dropping him off for college." —⁠ Molly,

    Trips from:
    US $650

    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:
    US $825
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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

3.0
/5
Based on 31,731 reviews by FishingBooker anglers

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