Striper charters, Sankaty Head, and the Chicken Box at midnight
Cisco Brewers for the all-day yard with the food trucks and the Grateful Dead cover band, oysters at 167 Raw, dinner at the Straight Wharf, a beer at the Chicken Box if anyone has a second wind. Charter with Captain Tom at Topspin for bonito and bass off Great Point, lunch at Millie's in Madaket facing the sunset. Bring linen, book the ferry early, the island doesn't bend for last-minute groups.
golf • 5 hr
Bluff links with the red-striped lighthouse on 6 — member guest-play only
fishing • 5 hr
Captain-run striper + bluefish run — back by lunch
brewery tour • 3 hr
Open-air brewery + distillery + winery on one lot
walking tour • 2 hr
Rose-covered cottages along the eastern bluff to the red-striped lighthouse
bar • balanced • $$
Island institution — live band every summer night since 1948
bar • balanced • $$$
Harbor-deck cocktails off the ferry dock
bar • balanced • $$
Dockside raw-bar pub with the sailing crowd
Coastal fine-dining • $$$$ • Best for: group-dinner
Upstairs dining room on Federal Street — reservation-only institution
Clam shack • $$ • Best for: lunch
Lobster-roll picnic off Washington Street, no frills
Brunch • $$ • Best for: brunch
BYOB cottage brunch — the line is the tradition
resort • Max 2 guests
Harbor-front grande dame — rose garden, Brant Point walk, breakfast on the porch
house • Max 10 guests
Rose-trellised east-bluff rental — private yard + outdoor shower
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