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Naples and San Marco, Florida
Warm up with a trip down I-75 to the sugar-soft sand and azure blue waters of Florida's Naples and Marco Island. In Naples, tropical umbrellas line the streets of downtown, where pastel stucco buildings house art galleries and boutiques. A few miles south of the multimillion-dollar homes lining Naples' waterfront, the wealthy on Marco stay at the sprawling Marco Island Marriott. But visitors staying at budget spots can enjoy the hotel's lavish spa, inventive restaurant and shelling cruises.
Santa Fe, New Mexico
Warmed by world-class art and nearly constant sunshine, Santa Fe offers a bright midwinter escape. An arts community launched by Wisconsin native Georgia O'Keeffe has grown to more than 200 galleries and a dozen museums. There's rarely a bad day for painting—or anything else, really—in Santa Fe, which sees 300-plus sunny days a year and enjoys the crystalline atmosphere of a 7,000-foot elevation. Take guided walks to learn about the area's history, debate red vs. green chile sauce on your enchiladas, and shop for art finds on the Turquoise Trail.
Texas' Hill Country
To some Midwesterners, Texas may come across as big and brash. But out in the Hill Country, 70 miles west of Austin in south-central Texas, the area that was home to Lyndon B. Johnson resonates with travelers eager to explore a side of the Lone Star State that somehow feels familiar. A getaway to Fredericksburg (population: 10,643), known for its carefully preserved Main Street, includes German heritage, fields of wildflowers, family-owned wineries, fine dining, and a Smithsonian-quality museum about World War II.
Lined with twisty, moss-draped oaks, the historic district of Savannah, Georgia, offers romantic inns, chic cafes and stirring glimpses of our nation's past. Tour the First African Baptist Church, a stop on the Underground Railroad; bite into ethereal crabcakes at Chef Joe Randall's Cooking School; breathe in the fresh sea air at Tybee Island beaches; and learn about the founder of Girl Scouts at the Juliette Gordon Low Birthplace.
Deep in the heart of Texas, winter visitors find sunny days, one seriously big capitol, an unrivaled live music scene and proof that locals continue to “Keep Austin Weird.” An average February temp of 55 degrees pulls people outside to enjoy golfing, wildflower walks, strolls around the lake and alfresco dining. Among the must-see stops: the Bullock Texas State History Museum, Ladybird Johnson Wildflower Center and the Lyndon Baines Johnson Library and Museum.
When it's cold in the Midwest, spring's already on the way in this Old South enclave along the Mississippi River. Tour white-columned mansions and enjoy warm breezes along with genuine small-town hospitality. Be sure to see Stanton Hall, one of the grandest and largest antebellum homes in the area; Monmouth Plantation, built in 1818 and now a hotel; and Longwood (pictured), a giant octagonal mansion that was only partially finished before the Civil War started.