Key West
For the perfect winter escape, set out to Key West and bask in its tropical-Victorian-fantasyland feel, Jimmy Buffett/Margaritaville vibe, and hedonistic laissez-faire attitude. Indeed, this southernmost bit of the continental United States has plenty to tempt visitors, whether you're interested in snorkeling – North America's only coral barrier reef is found here, and you can swim with dolphins or discover shipwrecks – or into history, culture, and art, which this quirky beach town has plenty of. You could easily while an afternoon strolling through Bahama Village, a quaint neighborhood favored by Ernest Hemingway (when you're done, you can also visit his house, Ernest Hemingway Home); other worthy local highlights include the Harry S. Truman Little White House and the Mel Fisher Maritime Heritage Museum. Come dusk, Mallory Square hosts nightly sunset celebrations, with musicians and street performers serving as backup for the magnificent sunset show that illuminates the Gulf of Mexico, while street cafés and open-air bars invite you to partake of the carefree atmosphere. However you spend your day, rest assured that local priorities are where they should be – fun comes first!
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New Year's Eve Cruises from $499 Editors' Review
December cruises to sunny ports for under $200 Editors' Review
$399+: Caribbean 7-day cruise on Costa Fortuna VacationsToGo.com
$279+: 5-day Caribbean winter voyage from Tampa Travelocity
$189+: Quick 4-nt Caribbean cruise w/Cozumel VacationsToGo.com
$539+: Peak-season 7-night MSC Caribbean cruise Cruise Holidays
$474+: 7-day Caribbean sail from Tampa w/Key West Cruise.com
$349+: 5-day winter Caribbean cruise from Tampa VacationsToGo.com
$299+: Holiday cruises to popular ports Orbitz
$499+: Dominican Republic & Mexico cruise on MSC VacationsToGo.com
$549+: 7-nt Galveston sail to Bahamas & Key West Carnival
$139+: Royal Caribbean 4-night Bahamas sailing CruisesOnly