Set sail around the scenic waters of Martha’s Vineyard aboard Our Passion, a beautifully maintained 1983 Pearson 422 Sailing Yacht operated by Martha’s Vineyard Charter Company.
"My wife and I booked a last minute sunset sail and were pleasantly surprised to get a confirmation so quickly." — Michael,
Set sail on the beautifully restored 1980 Nautical Development 56 Sailing yacht, refreshed in 2024, and based out of picturesque Martha's Vineyard.
A fun time to cruise up and down the north shore of the Vineyard and see the island from a water view. We leave from Tahmoo Harbor and cruise down the North shore coast or over the the Elizabeth Islands.
"Captain John was awesome! My family had such a great time on thr water." — Tania,
Experience the beauty of Cape Cod from the water with our scenic boat tours and sunset cruises through the pristine waters of Popponesset Bay in Mashpee, Massachusetts.
"Enjoyed a 2 hour sunset cruise with Chris and Bri, they were wonderful!" — Anita,
Our shark dive adventures are the culmination of many years in the waters we operate. We currently sail from S. Yarmouth, Martha’s Vineyard, and Nantucket. Our vessel Fins has been outfitted to run at speed with our super-strong, custom-built cage.
Step aboard In The Net Sportfishing, a 2021 Grady-White Fisherman 257 center console designed for speed, comfort, and serious on-the-water adventure out of Barnstable.
"We had a non-fishing expedition with Captain Benjamin, and he did a wonderful job keeping my non-water-friendly mother happy and calm as we toured the bay." — Susanna,
Discover the beauty of the Cape with Fishon Boat Tours aboard a sleek 2018 Cobia 261 Center Console, departing from Wareham.
Obsession Tours is a beautifully restored 1989 Blackfin 1 Sportfishing (refitted in 2011), operating out of Falmouth and offering an unforgettable private boating experience for up to 6 guests.
"Captain Luke was extremely knowledgeable about Martha’s Vineyard and the islands and an experienced boater." — Yvonica,
Summers on Cape Cod and in Plymouth, MA, are made for unforgettable days on the water with family and friends. Join Fishy Business Sportfishing for a fully customizable private boating experience designed around your ideal day at sea.
"My friends and I had a great time celebrating my birthday. The Cap." — Savanna,
Discover why Vineyard Haven is a favorite launch point for coastal adventures on Martha’s Vineyard. Sheltered by a deep, well-protected harbor, this charming port town sets the stage for smooth departures and easy returns—perfect for first-time cruisers and seasoned skippers alike. With Vineyard Haven boating charters, you’re minutes from scenic shorelines, quiet coves, and open stretches of Vineyard Sound.
Set your course past classic New England waterfronts, working marinas, and bobbing sailboats as you slip into crystal-clear channels. Many trips trace the island’s northern edge toward iconic lighthouses and sandy points, while others tuck into tranquil spots like Lagoon Pond and Lake Tashmoo for swimming, paddle breaks, or a picnic on the hook. Keep an eye out for seabirds and occasional seal sightings along the way.
Conditions here often bring gentle breezes and manageable seas, ideal for sailing days, family outings, and sunset cruises. Powerboat tours make quick work of the coastline, opening up time for beach stops and snorkeling in calm anchorages. If you’re angling to add fishing to the itinerary, local captains can suggest timing and tactics for inshore species common to these waters.
From carefree half-day excursions to custom island-hopping itineraries, Vineyard Haven boating charters blend classic Vineyard scenery with flexible trip options. Come for the postcard views, stay for the easygoing harbor vibe—and head home with an unforgettable day on the water.
