Warmth and good cheer abound in the island city of Key West this festive season with quirky celebrations taking centre stage. From lighted boat parades to the chance to ‘Smooch a Pooch,’ there’s an ‘only-in-the-Florida Keys’ holiday event for every visitor.
27 November – 31 December: Key West Holiday Fest. Seasonal celebrations begin at the Key West Historic Seaport with the Lighting of the Harborwalk on 27 November at 6 p.m. The harborwalk area (from Greene to Grinnell streets) will glimmer with maritime-themed holiday displays and offer unique events throughout the season. Other festival highlights include tours of historic lighted inns throughout Old Town Key West, and a boat parade with decorated, lit-up vessels and good cheer. Visit keywestholidayfest.com.
6, 12-14, 16-19, 21-23 December: Old Town Trolley’s Holiday Lights and Sights Tours. The popular green and orange sightseeing trolleys, festively adorned with holiday lights, showcase ‘Christmas Chill’ in Key West’s best-decorated historic neighbourhoods, buildings and homes in fun-filled 60-minute excursions. Tours depart from Mallory Square; treats include cookies and hot cider. Visit trolleytours.com.
14 December: Parade of Paws and Holiday Bazaar. The sixth annual pet parade at Higgs Beach Dog Park at Atlantic Boulevard and White Street supports the Florida Keys SPCA animal care fund. Attractions at the 10 a.m. to 2 p.m. event include photos with Santa, goods by local vendors, entertainment and a ‘Smooch a Pooch’ booth. Visit fkspca.org/events-and-news/upcoming-events.
19, 20 and 21 December: Sugar Rum Cherry: A Burlesque Nutcracker. Inspired by the holiday classic ‘Nutcracker’ ballet, this spirited and naughty two-act ‘reverie’ is presented by Key West Burlesque. Clara, a young ingénue, celebrates the season with sugar rum cherry cocktails and is transported in a dream to the ‘Land of Libations.’ The performance plays at the Key West Theater. Visit thekeywesttheater.com.
27 and 28 December: Home Tours ‘Holiday Style.’ The Old Island Restoration Foundation’s Key West Home Tours are among America’s oldest and longest-running, dating back to 1960. This 60th annual series features self-guided tours of five Key West homes and gardens, all festively dressed for the holidays. Visit keywesthometours.com/60th-season-home-tours.
31 December: Annual Key West Dachshund Walk. Spectators can meet and greet as many as 200 dachshunds -- many of them costumed -- in a ‘wiener wonderland’ on Fleming Street between Whitehead and Duval streets. Starting at noon, canines and proud owners stroll through a portion of the island’s picturesque downtown during this much photographed event. Visit facebook.com/Key-West-Dachshund-Walk-161327957238019.
31 December: New Year's Eve ‘Drops’ in Key West. Ring in 2020 with a ‘conch shell drop’ at Sloppy Joe's Bar on Duval St.; the descent of a super-sized red high-heel shoe carrying drag queen Sushi at the Bourbon St. Pub/New Orleans House complex; the lowering of a pirate wench at midnight from atop a tall ship’s mast at the Schooner Wharf Bar; and a huge replica of a Key lime wedge splashing down into a larger-than-life margarita glass at Ocean Key Resort & Spa. Revellers can also witness the ‘flight’ of a uniformed ‘stewardess’ in a section of a replica aircraft at First Flight Island Restaurant & Brewery, the building known as the birthplace of Pan Am, and the ‘tuna drop’ at the Smokin’ Tuna Saloon. Visit sloppyjoes.com, bourbonstpub.com, schoonerwharf.com, facebook.com/SunsetPierKeyWest, firstflightkw.com and smokintunasaloon.com.
A complete guide to events throughout the Florida Keys is available at fla-keys.com/calendar.