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.
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,
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,
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,
Discover the beauty of the Cape with Fishon Boat Tours aboard a sleek 2018 Cobia 261 Center Console, departing from Wareham.
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.
ON THE EDGE – Your Ultimate Luxury Family Adventure Machine, Fully-Restored Grady-White Gulfstream 232 Walkaround.
"Captain Rick is very friendly. On the Edge is kids friendly." — Jaya,
Keepin’ it Reel Fishing Charters is a 2006 May-Craft Pilothouse 27XL designed for comfort, speed, and unforgettable days on the water.
Chilmark, Massachusetts is a scenic up-Island escape on Martha’s Vineyard, prized for its rugged coastline, quiet ponds, and a timeless maritime vibe. This is where classic New England charm meets crystal-clear horizons, making it a favorite launch point for Chilmark boating charters. From the working harbor at Menemsha to the protected waters just inside the salt ponds, you’ll find an inviting mix of calm, family-friendly routes and open-water passages that reward curious cruisers and photographers alike.
Hop aboard to explore sheltered coves, trace dramatic headlands along Vineyard Sound, and savor golden-hour views that turn the shoreline into a postcard. Local captains know the tides and channels by heart, guiding you to smooth rides, great swimming spots, and memorable wildlife sightings. Whether you’re planning a relaxed harbor tour, a shoreline picnic at anchor, or a half-day adventure threading between sandy spits and rocky points, Chilmark boating charters deliver that “secret side of the Island” feel—without the crowds.
Calm mornings are ideal for family outings and paddle-friendly lagoons, while breezier afternoons invite coastal cruising and sunset circuits past classic Vineyard scenery. Bring your camera for fishing boats returning to port, rustic docks, and wide-open seascapes. With flexible itineraries that can include beach views, lighthouse vistas in the distance, and unspoiled stretches of shoreline, Chilmark boating charters are your gateway to the Vineyard’s wild beauty—seen best from the water.
