Go big or go home this holiday season with four vacations that make great gifts, each with something for the city explorer, beachcomber, ski bunny, and wine lover.

1. New York

After you see the places you came to visit—Rockefeller Center for ice skating, the windows at Macy’s Herald Square, the Nutcracker at Lincoln Center—go where the locals go: the Lincoln for chef Jonathan Benno’s spaghetti pomodoro, the John Dory Oyster Bar for happy hour, Madonia Brothers Bakery in the Bronx for a fresh cannoli (2348 Arthur Ave.), De Vera  for objects d’art, McNally Jackson for indie books, and Brooklyn’s Dead Rabbit for a hot toddy. Get more untouristy tips at Condé Nast Traveler.

2. Cayman Islands

With direct flights via Cayman Airways, this popular Caribbean retreat for Chicagoans is a foodie’s dream vacation from January 16 to January 19, when the four-day Cayman Cookout  comes to town. No ordinary food and wine fest, this beachside event summons big-name culinary talents such as Anthony Bourdain, Eric Ripert, José Andrés, Daniel Boulud, Lidia Bastianich, and Chicago’s own Rick Bayless. For the finale, hang out together at a barefoot BBQ by the sea.

3. Park City, Utah

This year’s ski season will get a big boost from the fast-approaching Sochi Winter Olympics. Now through the end of the season, Park City is a great place to take the athletes and adrenaline junkies in your world; you might still catch Olympians in training and you’ll be able to partake in the full-blown bobsled and skeleton tracks, which are among the hair-raising, open-to-the-public thrills left over from the last Winter Olympics. Stay at the Waldorf Astoria Park City (from $650) for another bonus available only to guests: a private skating lesson with Patrick Meek, an Olympic hopeful on the U.S. National Speedskating Team ($120). Tweak up your bundled-up look with a free style consultation at Cole Sport.

4. Mendoza, Argentina

Oenophiles who have tired of Napa and Sonoma should go instead to South America’s stunning wine country. Set to open this month, the 22-villa Vines Resort & Spa  (from $800) sprawls across 1,500 acres of Mendoza’s Uco Valley, the Andes gleaming in the backdrop. Take part in a wine camp experience led by winemaker Santiago Achaval or buy your own three-to-10-acre plot of Argentine vineyard from which you can produce your own small-batch wine. Also on tap at the Vines: gaucho-style, open-flame cuisine at Siete Fuegos; a 100-plus-square meter infinity pool above the vineyards; and a subterranean spa.