Jimmy, the James Hotel, New York

For arty Manhattanites (and Gotham visitors who don’t venture above 14th Street) this indoor/outdoor space, which opened atop the 18th floor of Soho’s James Hotel in 2011, epitomizes creative cool. Lounges around the teak-decked pool offer stunning views of the historic Woolworth Building and the Brooklyn Bridge; artisanal ingredients infuse the cocktails (try the Mexican Bee Hive, made with single-barrel tequila, lavender syrup and a chunk of honeycomb). Small plates from in-house restaurant David Burke—lobster and fennel dumplings, pretzel crab cakes and maple-bacon dates served with dollops of peanut butter—are equally delicious. Cocktails from $17; jimmysoho.com.