Bar at Galley Beach
A venerable, family-owned restaurant since 1958, the Galley—where untold numbers of Nantucketers have celebrated their anniversary dinners—is the perfect place for a sunset cocktail. By day, the elegant, rattan-furnished open-air dining room (which looks right onto the colorful beach umbrellas of the Cliffside Beach Club) still draws old-guard regulars, who pair their Pernod-infused escargots with wine by the glass.
At night, a decidedly trendier scene unfolds in the back room and on the torch-lit beach lounge (where St. Bart's-style couches sit right on the sand). Here, a young, rich, and expensively dressed crowd canoodles over creative cocktails—like the Painkiller with British Navy Pusser's Rum, pineapple and orange juice, cream of coconut, and shaved nutmeg—and gets increasingly lively as the night wears on.