With just one street of small shops, surrounded by beach, dunes, grass, mixed forest and vast saltwater ponds, Menemsha feels seductively like the edge of the world.

Nantucket’s gentle island landscapes, seafaring traditions, cobblestone streets and comfortable sense of wealth make it the Grail of regional cruising.

Oak Bluffs has unabashedly welcomed summer visitors for over 150 years. It’s hard to visit without getting swept up in the resort-town energy.

Running almost 9 miles from the elbow of the Cape at Monomoy to the northern tip of Nantucket, the Rip is a ridge of shifting sand, cut through with a handful of shifting channels.

In the age of sail, Vineyard Sound was among the world’s busiest sea lanes. When those vessels needed shelter from hard weather or a foul current, it was an obvious choice – easy to enter and close to their route.