The Club Car
This downtown institution, which partly occupies an early-1900’s Pullman train coach, is actually a full-scale restaurant. But though islanders have enjoyed fine traditional meals here for 40-odd years (standby menu items include Maryland crab cakes, beef Wellington, and “Oysters Charlemagne”), late-night cocktails and live piano music in the cozy, low-roofed bar (inside the train car) are absolutely legendary. You simply haven’t done Nantucket until you’ve gathered around Tony the pianist for boozy, wee-hour group renditions of show tunes, “Bennie and the Jets,” and “I Will Survive.”
Tip: If there’s one place on the island where you should drink G&T’s, it’s here. Have the bartender make yours with Hendrick’s gin—it has an especially summery, rose-and-cucumber kick.