With all the talk about the annual Fishing Derby, I can’t help but think about a different kind of fishing – the kind that has you cared for, charter style.
If it is bigger fish you’re after than there are numerous charter-fishing boats available from all ports of the island and most guarantee you’ll catch more fish than you want! Captains of these boats are knowledgeable, familiar with the island’s waters and fish and are excited to work with fishing enthusiasts of all skill levels.

Here are some of my favorites:
Menemsha Blues Charters run by Captain Jonathan Boyd not only boasts “Fish Guaranteed,” but is captained by a former Harbor Master of the busy Menemsha harbor. Climb aboard the 31-foot Mary Sea and head out into the deeper waters for a yield of striped bass and bluefish.

Capt. Porky’s Fishing Charters run by Captain Everett “Porky” Francis has won the Best of the Vineyard for Charter Fishing and runs both in-shore and off-shore charters as well as half and full day excursions. The 30-foot Blackwatch White Water heads out of the docks in Edgartown and is open seven days a week.

Flashy Lady Charters run by Captian Dick Vincent may be your best bet as their slogan is “No Bass – No Pay!” The boat record is a monster 55 pounder striped bass. Captain Dick has catered to many other satisfied customers over the last 13 years as a charter captain. The Flashy Lady is a traditional 26-foot bass boat that carries a maximum of four adults and leaves Menemsha twice-daily Rain or Shine!