New England / Martha’s Vineyard
Edgartown Harbor
Vineyard Haven Harbor
Menemsha Harbor
Katama Bay
Cape Pogue Bay
Tour the Aquinnah Cliffs
Ride the Flying Horses Carousel
Bike the Correllus State Forest trails
Visit the Martha’s Vineyard Museum
Watch the sunset at Menemsha Beach
Edgartown
Oak Bluffs
Aquinnah
Menemsha
Chappaquiddick Island
Late June through early September brings the warmest water and the island’s full social calendar, though July and August also bring the heaviest ferry and mooring traffic. Many charter guests prefer the shoulder weeks, mid-June or September, when the crowds thin, restaurant tables are easier to find, and the Vineyard Sound side of the island stays comfortably swimmable. The Striped Bass and Bluefish Derby each autumn also draws a lively crowd of anglers without the peak-summer congestion.
Martha’s Vineyard Airport (MVY) takes private and commercial flights and sits a short drive from Edgartown and Oak Bluffs. Most vehicle and passenger traffic, though, arrives by ferry from Woods Hole on Cape Cod, a crossing of about 45 minutes. Yachts typically clear in and moor at Vineyard Haven or Edgartown, both of which have harbormaster moorings and full marina services during the summer season.
Edgartown Harbor and Vineyard Haven Harbor are the most protected and best equipped, with launch service, fuel and provisioning close by. Menemsha, on the island’s quieter west end, is a working fishing harbor with a handful of moorings and some of the best sunset views on the Vineyard. Katama Bay, behind South Beach, is shallow and better suited to smaller tenders than deep-draft yachts.
Three to four days lets you split time between Edgartown’s harbor-town energy, Oak Bluffs’ beaches and cottages, and Menemsha’s quieter fishing-village pace, with a full day free for the Aquinnah cliffs. Guests combining the Vineyard with Nantucket or the Elizabeth Islands often extend to a full week, since the crossing between islands is short but the pace on each is worth slowing down for.
The Martha’s Vineyard Striped Bass and Bluefish Derby runs five weeks each autumn, from September 20 to October 18 in 2026, and is now in its 81st year. It’s a genuine island institution, drawing boat and shore anglers competing for striped bass, bluefish, bonito and false albacore, with nightly weigh-ins that turn into informal social gatherings. Even non-anglers enjoy the atmosphere it brings to Edgartown and Oak Bluffs during what’s normally the quiet start of the off season.