Best Hotel Bar in Boston: City-Bar at the Lenox Hotel

Though it's located inside the historic Lenox Hotel—the tallest building in Boston when it opened in 1900—City-Bar is full of modern touches. The space is sleek, elegant and small enough to seem intimate. You can lean back in comfy leather couches and kick your feet up onto ottomans or mingle at the long wood bar, where progressive bartenders mix classic sidecars alongside oddball concoctions like the Willy Wonka (Van Gogh Dutch chocolate vodka, Godiva cream chocolate, crème de cacao). They also feature a killer selection of single malts, cognacs, ports, tequilas and liqueurs. Even chef Robert Fathman, from the hotel's Azure restaurant, contributes to the bar: He makes his own "infusions diabolique," including a terrific bourbon infused with figs, cinnamon and vanilla bean. With its sexy, warm lighting, it is perhaps Boston's best date space. And best of all, you can actually hear yourself talk. Not always easy in this town.