Water Street Cafe
Up the stairs from this restaurant’s main dining room (where patrons tuck into simple-yet-sophisticated dishes like yellowfin tuna tartare and plum-glazed, slow-roasted pork loin) is one of the most happening nightspots in town. Clubby and wood-paneled, with a wraparound bar and cozy leather banquettes, the space fills in the evening with a lively mix of Nantucketers: young pretties in minidresses, just-off-shift local retailers and café workers, blue-state politicos, and visiting couples happy to have stumbled onto such a rollicking cross-section. Head bartender Graeden Ambrose keeps everyone happy pouring some of the island’s most delicious cocktails; his specialty, the Enter the Dragon, is made with fresh-squeezed orange and lime juices, orange-infused vodka (from the local Triple Eight Distillery), and kalamansi-lime honey (from the Philippines), and finished with a dusting of cayenne pepper.
Tip: If you get hungry, the entire menu from downstairs can be ordered at the bar.