Calendar of Events

The Southernmost City celebrates with a conch shell drop at Sloppy Joe’s Bar, 201 Duval St.; a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St.; and a pirate wench descending from a tall ship mast in the island city’s Historic Seaport.

The back bay is the setting for the annual New Year’s Eve fireworks extravaganza hosted by Sundowners, Senor Frijoles, Cactus Jacks, Gus’ Grille at the Marriott Key Largo Beach Resort and the Caribbean Club, MM 103-104. Check website for details.

Lighted and decorated vessels from rowboats to tall ships proceed around Key West’s Historic Seaport and harbor areas. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport.

A middle Keys holiday kick-off event for more than 15 years; watch as dinghies, mega-yachts and anything in between turn the harbor into a sparkling procession along the parade route. Best viewing sites include Lazy Days South, Marathon Marina, Sombrero Dockside Lounge and Burdine’s Waterfront. Starts at dusk, near 5 p.m.

Blackwater Sound is to shimmer as decorated boats parade along the shoreline in celebration of the holiday season. The best viewing and libations are to be found at Sundowners, Senor Frijoles, the Marriott Key Largo Bay Resort and Caribbean Club, MM 103-104.

Part of the acclaimed Redbone at Large series of tournaments, this all-release tournament offers anglers a chance to pursue sailfish in Captain Don’s memory. Up to four anglers can fish per boat.

This extravaganza begins with a tree-lighting ceremony at Founders Park, MM 87. A holiday parade follows, featuring Santa, food, kids activity booths and live “on stage” performances. A mountain of snow is the favorite among mitten-clad munchkins.

A winner-take-all prize of up to $30,000, along with the prestigious Captain’s Cup, is to go to the top boat team – each team is allowed up to four anglers per boat. The guaranteed cash prize is based upon the number of boats registered for the one-day event; for a field of 15 registered boats the top payout is to be $20,000, for a field of 20 boats, payout increases to $25,000 and a full field of 30 registered boats ensures a grand prize of $30,000. The all-release tournament is limited to 30 boats. Entry fee $2,500 per boat for first two anglers; third angler is $300, fourth angler $200.

A vibrant three day festival and art walk celebrating all of the arts in Key West: visual, performing, literary, film, musical events, performances and exhibitions. Galleries are to have extended hours and exhibitions. Art and culinary pairings are to be offered in local restaurants as well.

The first leg of the triple-crown Florida Keys Gold Cup Championship Series is characterized by high-flying sail action, conservation and sportsmanship. It’s also the only tournament in the Gold Cup series to offer a junior division for anglers aged 16 and younger. Unlimited anglers are allowed per vessel.