Seven miles off the elbow of Cape Cod, Martha's Vineyard has drawn summer crowds since the 19th century, when Methodist families pitched tents at Oak Bluffs for revival meetings and later replaced them with the candy-colored Gingerbread Cottages that still ring the campground today. The island stitches together six very different towns, from the white-fenced sea captains' houses of Edgartown to the fishing shacks of Menemsha and the Wampanoag homeland at Aquinnah, where the clay cliffs glow at sunset.

The Vineyard rewards a leisurely pace. There are no traffic lights to speak of, the food leans heavily on what comes off the boats that morning, and the best afternoons are spent licking ice cream cones, browsing independent bookshops, and watching ferries slide in and out of the harbors. It is genuinely family-friendly: kid-pleasing carousels and beaches sit comfortably alongside museums, wine bars, and serious seafood.

Getting here means a ferry, most often the Steamship Authority from Woods Hole into Vineyard Haven or Oak Bluffs (foot passengers have the easiest time in summer). On-island, the VTA buses are cheap and frequent, bikes are everywhere, and a rental car helps for Up-Island exploring. Come between late May and early October for full restaurant and ferry schedules; July and August are liveliest, while June and September trade some warmth for smaller crowds and easier reservations.