When To Go
High season is mid-December through March, followed closely by the summer months when Key West is flooded with families on vacation. Low season is late summer and early fall – also the height of hurricane season. You'll get the best bang for your buck in late November through early December, plus mild temperatures, low prices, and fewer crowds. April and May can also offer good values, with the exception of spring-break weeks.
However, it's not quite as simple as defining high and low because there are also a number of parties, festivals, competitions, and events that can temporarily turn low season into high and high into super high. Beyond the usual holidays (Memorial Day and Labor Day weekends, Christmas, Fourth of July, etc.), particular ones of note include June's gay Pridefest (www.pridefestkeywest.com); July's Hemingway Days/Lookalike Contest; the Battle of the Bars in August; September's Womenfest; the huge blowout Fantasy Fest in October; and November's Parrotheads in Paradise. For other events, check the local chamber of commerce online events calendar (www.wliinc3.com).
When To Go
High-season
Mid-December through March
Low-season
Late August through Mid-October
Best bang for your buck
November through early December
$279+: 5-nt exotic cruise to Western Caribbean ports from FL Royal Caribbean
$125+: Key West, Cococay & Nassau 4-nt cruise from Miami Royal Caribbean
$349+: Caribbean & Cancun 7-night cruise on MSC Poesia MSC
76% off Caribbean and Bahamas Cruises from Baltimore Editors' Review
$334+: Cheap 7-nt winter cruise to Western Caribbean cities Cruise.com
$334+: 7-nt Montego Bay & Key West cruise, kids sail free Cruise.com
$164+: Bahamas 4-nt cruises with $25 onboard ship credit Royal Caribbean
$149/nt+: Key West beachfront hotel w/4th nt free & champagne Perfect Escapes
$109/nt+: Key West hotel w/pool & 2 restaurants Travelocity