Striper charters, Sankaty Head, and the Chicken Box at midnight
Nantucket keeps it honest under the shingles: striped-bass charter before 9 and back for lunch, Sankaty Head links in the afternoon, Cisco out back for the brewery hour, Chicken Box for the live band at midnight.
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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