Hands down the wildest party in the Florida Keys, the 10-day Fantasy Fest attracts thousands of people to Key West every October for a hedonistic warm-up to Halloween. The festival remains the island's busiest -- and naughtiest -- stretch of days, so be prepared to see big crowds, skin-baring costumes and rowdy celebrations. Originally developed to draw tourists during the otherwise quiet time between summer and Christmas, the festival today brings more than 100,000 people to Key West, with events that include a Royal Coronation Ball (where 2 locals are crowned Conch King and Queen), a street fair, drag queen contests and the pet masquerade costume contest, all culminating in The Fantasy Fest Parade. Additional popular festival events include a burlesque show, a Western-themed party at Cowboy Bill's Bar and "Wharfstock," a hippie-themed concert.
Though it technically marks the start of the aforementioned Fantasy Fest, the Goombay Festival earns its own ranking because it stands alone as a 2-day, family-friendly street party, separate from Fantasy's other, less kiddie-friendly shenanigans. The Goombay, held on Petronia Street just off of Duval in the island's Bahama Village neighborhood, celebrates Caribbean, Bahamian and West African culture with arts and crafts, ethnic food like conch fritters and live music from groups such as the Steel Your Heart Band. Bring your sense of rhythm -- the festival's calypso-like live music carries on from noon to 11 p.m. and dancing in the street is highly encouraged.
The Key West Bight Marina, more commonly known as the island's Historic Seaport, bursts into holiday mode for a 6-week celebration -- the Key West "Bight" Before Christmas. The festivities begin on Thanksgiving eve with the lighting of the Harbor Walk of Lights, a 4-block stretch of the Harbor Walk along the Historic Seaport
with lights swathing every imaginable structure, from the Key West Ferry Terminal, to trees and shrubs and even underwater at the edge of the marina. The ongoing events include a holiday parade with floats and an appearance by Santa Claus, a tree-trimming party, a tour of local historic inns, a lighted boat parade and a holiday music concert. For a listing of event dates and times, check the festival website
New Year's Eve in Key West
If Christmas celebrations aren't your thing, head to Key West to ring in New Year's Eve, a generally raucous occasion with 3 unique spin-offs of New York City's Times Square midnight ball drop. On Duval Street, the island's main drag, join the thousands of people gathered in front of the iconic dive bar, Sloppy Joe's
to watch the “Annual Dropping of the Conch Shell,” where an enormous man-made conch shell is lowered from the bar's roof at midnight. Should female impersonators and gay bars be more your speed, head to the New Orleans-themed Bourbon St. Pub
, also on Duval Street, at midnight to see the drag queen, Sushi, in a fabulous gown, sitting inside a giant, red high-heeled shoe and lowered from the bar's roof to the street below. Finally, seafaring pirate lovers can head to the island's Historic Seaport
, where a scantily-clad pirate wench is lowered from the mast of a ship when the clock strikes 12, as cannons fire and live music plays.
Throughout the 1930s, the legendary writer Ernest Hemingway called Key West home, and today his legacy thrives during the annual Hemingway Days Festival -- an ode to the author which culminates in an epic lookalike contest (imagine dozens of pudgy, white-bearded men) held at Sloppy Joe's bar, one of Hemingway's favorite drinking spots. Other festivities include a short story competition for wannabe writers, a marlin fishing tournament ("Papa" liked to fish) and a fake Running of the Bulls to honor Hemingway's love of bullfighting. The festival is held every July, though fans of Hemingway can explore his history on the island year-round at his former abode, now the Hemingway Home and Museum
, open daily.