Montego Bay
This island may do duty as a spring-break central every year, but the reggae-centric spot has a fascinating history, vibrant culture, and passionate political past that make it an enchanting (and warm!) place to visit in winter. Jamaica offers travelers everything from picture-perfect white-sand beaches to river rafting; from spicy jerk chicken to some of the best golf in the West Indies. Catering to everyone – honeymooners, party-goers, and families alike – the island offers an array of accommodations from luxurious villas to all-inclusive resorts and out-of-the-way enclaves.
How: Board a direct flight to Montego Bay from Charlotte (United, US Airways; about 3 hours), Los Angeles (Air Jamaica, Delta; 5.5 hours), Memphis (Northwest; about 3.5 hours), New York (American, Continental, Delta; about 4 hours), Philadelphia (Delta, US Airways; about 3.5 hours), or Washington, DC (United, about 3.5 hours).
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$54+: Sale fares to Jamaica beaches (one-way) Air Jamaica
$108+: Mex. & Carib. fares w/$10 off (round-trip) CheapOair
$99+: Last-min Caribbean & Mexico fares (one-way) USA3000 Airlines
Jamaica Jazz & Blues Festival deals from $49 Editors' Review
$209+: Unique Mex/Carib cruises from southern US ports Editors' Review
$479+: 7-nt sail w/Jamaica & Grand Cayman–71% off Carnival
$499+: 7-day cruise from Galveston w/Montego Bay VacationsToGo.com