MASSACHUSETTS
Massachusetts is one of America’s most quietly compelling travel destinations, and Martha’s Vineyard is its crown jewel. The island sits seven miles off the coast of Cape Cod and operates almost entirely on its own terms — no chain hotels, no strip malls, no franchises. What it has instead is one of the most beautiful collections of historic towns in New England, some of the best seafood on the East Coast, and a summer atmosphere that has drawn American families back year after year for generations.
Our Massachusetts coverage is focused on Martha’s Vineyard, based on firsthand visits. Nothing here is sponsored.
Where we cover in Massachusetts:
Martha’s Vineyard — The Vineyard divides itself into six distinct towns, each with its own character. Our coverage centers on Edgartown — the most polished and historically significant of the island’s towns, with a Main Street lined with Federal-style captain’s houses, excellent restaurants, independent boutiques, and a working harbor that still feels genuinely connected to the island’s seafaring past. It’s the right base for most first-time visitors and the best town on the island for families. Read our full Martha’s Vineyard travel guide to Edgartown for the best restaurants, shopping, beaches, and family activities.
Winnetu Oceanside Resort — Located on the south shore of the Vineyard near South Beach in Edgartown, Winnetu is consistently rated one of the best family resorts in New England — and for good reason. It operates more like a summer camp than a traditional hotel, with a genuinely extraordinary range of activities and programming for kids of all ages, strong dining, and a beachfront setting that justifies the drive from the ferry. Read our full Winnetu Oceanside Resort hotel review for an honest account of what to expect.
Getting to Martha’s Vineyard: The island is accessible by ferry from Woods Hole on Cape Cod — the crossing takes about 45 minutes and runs year-round. In summer, ferries also run from Falmouth, Hyannis, New Bedford, and (seasonally) from New York and New Jersey. Book car reservations well in advance for summer travel — the ferries fill up weeks ahead during July and August.
Best time to visit Martha’s Vineyard: Late June through Labor Day is peak season — the island is fully open, the weather is warm, and the energy is at its highest, though prices and crowds reflect it. September is the Vineyard’s best-kept secret — warm water, fewer crowds, lower rates, and the island still fully operational. October brings beautiful fall color and a quieter, more local atmosphere. Much of the island closes or reduces hours from November through May.
