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It's your choice: Bask in tropical warmth, schuss over 20 feet of new-fallen snow or catch a popular spot at a time when crowds are thinner and prices lower.
Squaw Valley, California
More than half a century after it dazzled the world during the 1960 Winter Olympics, Squaw Valley remains the touchstone for American ski resorts. Nonskiers can savor the winter wonderland on a snowshoe trek through the forest, a ride on the Aerial Tram to High Camp for a whirl in the Olympic Ice Pavilion, or a glide through meadows of fresh powder in a sled pulled by Alaskan huskies. Après-snow, the pedestrian village's lively restaurants, shops and watering holes await.
St. Augustine, Florida
Established by the Spanish in 1565 and anchored by the seaside 17th-century fort known as Castillo de San Marcos, St. Augustine is the country's oldest city. The cobblestoned historic district further attests to its longevity with garden courtyards, museums, stately residences and other landmark buildings, and intriguing side streets that today are home to cafes, shops and funky bars. The history continues well beyond colonial days, too. In the late 1880s, Standard Oil cofounder Henry Flagler built three palatial hotels here: One is now a college, another is a museum and the third was restored in 1999 as the Casa Monica Hotel.
Jackson Hole, Wyoming
If your ideal winter vacation involves staying in a rustic cabin — with all the creature comforts — surrounded by snowy woods and icy peaks, then the Fireside Resort Jackson Hole, just outside Grand Teton National Park, has you covered. Its simple, compact cabins pay homage to the valley's original homesteaders. In addition to the requisite fireplace, they're equipped with pillow-top mattresses and down pillows, flat-screen HDTVs, Wi-Fi and colorful art. Doggie beds and fixings for s'mores are also available. The decks are roomy enough for snow gear, if you are so motivated, and free ski shuttles run hourly.
San Juan, Puerto Rico
Barely three hours from Miami, Puerto Rico delivers a Caribbean vacation free of customs, currency exchange, cellphone surcharges and premium winter prices. Well-preserved Spanish architecture — including some of the oldest European forts on U.S. soil and the 16th-century Ponce de León residence — contrast with San Juan's modern financial center and the Condado and Isla Verde beach resorts. The capital also has vibrant culinary and nightlife scenes. Several out-of-town attractions are nearby, including El Yunque rain forest to the east and, to the west, the Arecibo Observatory, which was featured in such films as Contact and GoldenEye.
Winter is low season in Red Rock Country, but Sedona's florid landscapes, sunsets and energy vortices are no less intense. The cool days (highs in the 50s to mid-60s, with a bit of ephemeral snow late in the season) are perfect for exploring state parks and national monuments or visiting sacred sites. And this is the most relaxed time to frequent the city's popular galleries, cafes and turquoise jewelry shops. You can also indulge in wine tastings, take art walks, enjoy concerts and plays, and participate in both physical and metaphysical workshops and healings.