It's an annual challenge: Where to make a pitstop, or where to end the day, after a harried holiday shopping trip around Union Square? There are, in fact, a handful of good and civilized options.
Our favorite time of year to hit this place is the holiday season because a) in the late-afternoon, early evening hours, no one even knows it's open, and b) their cocktails are far, far better than they were once upon a time. Take in the view and order a Smokey Local, a twist on the Manhattan with rye, Maraschino liqueur and a touch of a Scotch; or go with a group and have a bowl of the very Christmas-y Harvest Punch. (Warning: They do host a lot of private events, especially on weeknights, so check to find out what their public opening hour is.) 450 Powell Street
One of the neighborhood's easy-going drop-in bars boasts some solid food options as well as a very high-end cocktail selection from bar manager Kevin Diedrich and his team. The Negroni on tap is always a safe bet, but the drinks change seasonally and now you'll find some warming holiday fare like the Harvest Julep (Woodford Reserve bourbon, mint, and Hangar One Spiced Pear vodka). There's also a featured section this season celebrating American whiskies, and we'd encourage you to let the bartender mix you up something special on a whim. 401 Taylor Street
Tucked inside the Mystic Hotel, in case you didn't already know, is one of the cooler spots in the neighborhood, on the second floor, with the entrance near the mouth of the Stockton Tunnel. The bar staff isn't quite as polished as it was under the leadership of former manager Kevin Diedrich (now at Jasper's), but they are making some tasty original holiday drinks like the Cranberry Street (dry gin, amaro, cranberry sauce, absinthe, lemon). 417 Stockton Street
Cap off an exhausting day of bargain-hunting with some Latin-themed cocktails at this always solid spot just off the square. Our top suggestions: the Carmen Amaya (rittenhouse straight rye, cointreau, fresh lemon, muddled basil, and amontillado sherry), and an updated classic with luxe French ingredients, the Champs Elysees (pierre ferrand cognac, fresh lemon, green chartreuse, Cointreau and agave). 580 Sutter Street
Inside the Westin St. Francis are not one but three bars, two of which (off the lobby) are going to feel especially festive this time of year. Right now Clock Bar is doing a drink called A Breath of Autumn that's got barrel-aged gin, persimmon, Cocchi Americano, honey, lemon, and nutmeg; and Bourbon Steak (in addition to serving one of the best burgers in town) is serving an apple-y autumnal cocktail that is their Seasonal Crusta, with apple-infused Bulleit bourbon, lemon, and Maraschino liqueur. 335 Powell Street