Mexico City
JORGE CASTRO/TRAVEL + LEISURE
Though winter in CDMX won't have the tropical heat you might expect from Mexico — temperatures tend to top out in the low 70s this time of year — it still provides a balmy alternative to snowy U.S. locales. The capital is flush with cultural attractions, including first-rate museums (like the stunning Museo Frida Kahlo), incredible shopping at both high-end stores and local markets, and some of the best restaurants in the world (we're looking at you, Pujol). Make Las Alcobas your home base. The luxury hotel offers lavish guest rooms and a tranquil spa in which to relax after a day of urban exploration.
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Key West, Florida
NAPA74/GETTY IMAGES
Key West is a true delight in the winter months, as the average high temperature never really falls below 75 degrees. It's the perfect place for fruity cocktails on the sand, sunset strolls down lively shopping streets, and slice after slice of tangy Key lime pie. Make the most of your time here by booking a stay at the historic Casa Marina Key West, which recently underwent an extensive renovation. Through the hotel, you can book local food tours, golf outings, and sailboat cruises, or you can simply sit by the pool and soak in the Florida Keys sun.