The Florida Keys are kicking off the Christmas season by displaying the festive side to this winter-sun destination from 23 November until New Year’s Eve throughout the 125-mile-long island chain. From Key Largo to Key West, the 2022 Christmas season features spirited events such as lighted boat parades, historic inn tours, only-in-the Keys frivolity, sparkling waterfront celebrations and other island festivities.

Select Keys festive events are outlined below, while additional Florida Keys & Key West events can be found at and

Special Christmas Tours

Old Town Trolley’s Holiday Sights & Festive Nights ToursDiscover a new way to experience charming old town Key West. From 8-23 December, the popular green and orange trolleys, festively adorned with holiday lights, will showcase Key West’s best-decorated neighbourhoods, buildings, and homes on fun-filled 60-minute excursions. Tours depart each evening from Mallory Square at select times between 6:30-8:30 p.m.

Holiday Historic Inn Tours: On 9 and 16 December, explore Old Town Key West’s unique historic inns on evening tours (6-8pm) that offer the chance to glimpse lavish decorations and experience holiday cheer, treats at bed-and-breakfast properties and two popular Key West attractions.

Christmas Boat Parades

From 9-11 Decembervisitors can admire spectacular Lighted Boat Parades in various areas of the Florida Keys (Stock Island, Key West, Key Largo, and Key Colony Beach). Lighted and festively decorated boats will cruise waters surrounding the island chain. For further details on each event, see below:

New Year’s Eve ‘Drops’ in Key West

Ring in 2023 with a ‘conch shell drop’ at Sloppy Joe’s Bar. 2022 marks the 25th anniversary of the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex on Duval St.; the lowering of a pirate wench at midnight from atop a tall ship’s mast at the Schooner Wharf Bar on William St.; and a huge replica of a Key lime wedge splashing down into a larger-than-life margarita glass, paired with a performance by The Beatle Band, at Ocean Key Resort & Spa on Duval St. Revellers can also witness the ‘flight’ of a uniformed ‘stewardess’ in a section of a replica aircraft and enjoy a ticketed Gatsby-style party at First Flight Island Restaurant & Brewery on Whitehead St., known as the birthplace of Pan American Airways. In addition, there’s a ‘tuna drop’ at the Smokin’ Tuna Saloon on Charles St.

For more information on the Florida Keys & Key West, visit