Cuttyhunk Island

Duck inside the peaceful, protected harbor and call Cuttyhunk Marina, (508) 990-7578, at the town wharf for short-term dockage. For moorings, contact Jenkins Moorings, (508) 996-9294, or Frog Pond Marine, (508) 992-7530.

Once ashore you can wander the hilly slopes of town for amazing views of Vineyard Sound and Buzzards Bay, play in the surf at Barges Beach, grab a hot dog at Bart’s Cart or cast for stripers or bluefish in one of the greatest surfcasting venues in the world.

If you choose to spend the night, be sure to hail Cuttyhunk Shellfish Farms, (508) 971-1120; which will deliver ocean-fresh oysters and other raw-bar items direct to your boat.