Welcome to Annalee Charters

The waters around Martha’s Vineyard including Cuttyhunk, Noman’s Land and the Elizabeth Islands are known for some of the best fishing in the Northeast. The Atlantic Ocean, Vineyard Sound, Buzzards Bay and Nantucket Sound.Many species of fish travel through and live in the varied habitats, such as shipwrecks and deep ledges, providing the right temperature for all fish. Our Charter fishing mainly targets striped bass, bluefish, false albacore, bonito, black sea bass and fluke. Come out and experience an ideal family activity for all the ages.

Charter fishing aboard the “Annalee” with Capt. Annette Cingle will give you a rewarding experience with wonderful memories. If it is your first time fishing there is nothing more thrilling than fighting and landing your first fish! It will also teach you patience and perseverance useful life skills while enjoying your trip. Our style of fishing is trolling, casting and diamond jigging. We use light tackle gear to heavy tackle. You all will learn to appreciate the ocean and the dinner it provides for you.

Many people from all over the world come to Martha’s Vineyard to go Charter Fishing with a local guide. An adventure to go fishing with friends and grill up your catch for dinner! All you need is food, drink and sunscreen and Capt. Annette will provide the rest. Try to come for the Striped Bass and Bluefish Derby Tournament! Usually runs five weeks from Mid-Sept through mid October! Fantastic fishing event for all ages with lots of prizes and loads of fun! Maybe you can win your own fishing boat or a new vehicle for biggest fish!

Martha’s Vineyard Charter Fishing

Come fish with us on the “Annalee” from Menemsha! Our 22 foot Boston Whaler Center Console comfortably fishes two to three people. A fun-filled day of fishing! You’ll depart with experience after experience. An ideal trip for beginners and children. all you need is food, beverage and sunscreen. All other gear is provided. We fillet your catch for dinner or if you prefer catch and release so be it.


Cuttyhunk Drop Offs / Pick Ups

Take a boat ride over to Cuttyhunk for an early breakfast at the Cuttyhunk Fishing Club and a walkabout the small island with its amazing views and beaches. Cuttyhunk is a buzz with piping plovers, terns, american oystercatchers and most varieties of New England’s wildflowers, bayberry, sweet peas and host of other plant life. Cuttyhunk is about a mile and a half long and 3/4 mile wide with a natural harbor with a part of the island set as a nature preserve. Cuttyhunk Island is outermost island of the seven Elizabeth Islands in Massachusetts. Cuttyhunk is located between Buzzards Bay to the North and the Vineyard Sound to the South. Amazing views of Penikese Island, primarily a bird sanctuary and Nashawena Island, privately owned.

Annalee Charters
  • Martha's Vineyard Charter Fishing
  • Cuttyhunk Water Taxi