Menemsha pot-haul, Edgartown links, Ritz at midnight
State Road in West Tisbury for the long farm dinner, the Black Dog Tavern for the morning after, oysters at the Galley in Menemsha before the sunset everyone shows up for. Fish with North Shore Charters out of Menemsha Pond, lunch at the Bite for fried clams, drinks at the Ritz in Oak Bluffs. Rent a house in Chilmark, ferry the cars from Woods Hole, plan the trip around the tides not the bars.
fishing • 5 hr
Pot-haul with a working captain + shore bake on Lobsterville
golf • 5 hr
Members-guest all-organic course near Katama
fishing • 4 hr
Chappaquiddick wade-fishing with a local guide
walking tour • 2 hr
Clay cliffs + Wampanoag-land lighthouse at the west end
bar • chill • $$
Vineyard Haven harbor-front institution since 1971
bar • balanced • $$
Oak Bluffs dive + live music most nights — the late one
beer garden • chill • $$
Oak Bluffs brewpub with peanut-shells-on-the-floor energy
Farm-to-table • $$$$ • Best for: group-dinner
West Tisbury cottage with the up-island farm connection
Clam shack • $$ • Best for: lunch
Menemsha dock lobster + chowder — BYO wine on the jetty
Brunch • $$ • Best for: brunch
Vineyard Haven brunch — the line is also the tradition
resort • Max 2 guests
Edgartown Harbor icon — porch rockers face the lighthouse walk
house • Max 12 guests
Up-island acreage with pond + outdoor shower + private beach rights
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