Year-round balmy temps, palm trees and sandy beaches may not exactly scream “holiday season,” but while our friends up north are dreaming of sugarplums and freezing their bundled up behinds off, we here in the Florida Keys will be celebrating the season our way – with Conch Train Christmas tours (which are basically just an excuse to ooh and aah over Christmas light displays while we get sloshed on a trolley and make up dirty words to Bing Crosby’s greatest holiday hits) and parades and parties galore, sans the winter coats and frigid weather generally associated with the winter season.
That’s not to say life on the island is always easy breezy. The truth is, those of us lucky enough to call paradise home have our share of holiday stressors (even tropical island-dwellers have in-laws and get agita over sourcing the perfect gifts), but they pale in comparison to what our friends on the mainland have to suffer through each year. Having to scrape iguana poop off your conch cruiser (that’s Key West slang for a bicycle) is no picnic, but it sure beats having to scrape off three feet of icy shards from your Arctic incubator of a vehicle. So, if you’re fortunate enough to be joining us for the holidays this year, do yourself a favor and relax; we’ve got plenty of laid-back options for those looking to experience the season island-style.
When the weather takes a turn for the chilly (and for the record, that’s anything under 75) here in Key West, locals tend to (grossly) overcompensate for our climate’s lack of natural holiday décor. No snow-covered pine boughs or icicle-trimmed eaves ripe for adornment? Easy — cover your palm trees and hammock with twinkle lights (and toss some on your bike while you’re at it) and have Rudolph graze among the chickens and stray cats in the front lawn. Once the last of the corsets and headdresses from Fantasy Fest have been safely locked away, electricity bills begin to skyrocket as the competition for best-dressed house takes off across town. Starting right after Thanksgiving, Conch Train tours start offering special cookie-and-cider evening rides that tour the most magnificent light shows in town, while down by the bight, a festive Harbor Walk of Lights that runs from late November through New Year’s Eve and features a Fishing Buoy Tree, a fresh pine Nautical Christmas Tree and the original Key West Lobster Trap Tree, signifies that the season has really begun in earnest. From here, it’s a packed schedule of parades, concerts, parties, performances, tours and cinnamon-spiked drink specials. Here’s what’s on deck:
Key West’s conch cottages may not be covered in a light dusting of powdered sugar-like snow, but we still know how to decorate our homes to the nines. Every year, a number of epically creative locals cover their homes in lights and other holiday-inspired décor and engage in a little friendly competition. If you didn’t get to check out the entries on the official Key West Lighted Bike Ride on Dec. 4, from Dec. 6-23 you can still jump on one of the many Old Town Trolley Lights & Sights holiday tours and vote for your favorite holiday lights display. Along with the awesome sights and excellent narration highlighting fun facts about the island, you’ll also enjoy complimentary tasty treats like cookies and hot cider (and we hear some of the contestants even try to bribe the trolleys with candy and adult libations). The tour lasts about an hour and departs from Mallory Square. Find dates and times and purchase your tickets online at www.trolleytours.com/ key-west/christmas-holiday-tours.
Friday, Dec. 6, also signals the return of the Holiday Historic Inn Tour, a favorite among fans of Key West’s historic architecture. This year’s participating inns — The Gardens Hotel, Island City House Hotel, Amsterdam’s Curry Mansion Inn, The Weatherstation Inn and Hemingway Rum Co. Distillery on Dec. 6 and the Avalon Bed & Breakfast, Wicker Guesthouse, The Mermaid & the Alligator, Key West Butterfly and Nature Conservatory and Santa Maria Suites Resort on Dec. 13 — will deliver an eye-watering display and spread of festive treats for attendees, who are carted from place to place via trolley from 6-8 p.m. on both nights. Tickets can — and should — be purchased ahead of time at keystix.ticketforce.com.
On Friday, Dec. 6, those in town with pets should trek over to the end of William Street (on the Schooner Wharf side) to the Pet Pictures with Santa event from 6-8 p.m., hosted by local veterinary group All Animal Clinic and benefiting the Key West Boys and Girls Club. Because if you have a pup and you don’t Instagram a shot of him trying to lick Santa’s rosy nose, did Christmas even really happen?
This may come as a surprise, but the holiday season in Key West isn’t complete without a parade or two. On Dec. 7, the annual family-friendly Key West Hometown Holiday Parade leaves from Bayview Park at 7 p.m., winding its way down Truman Avenue and Duval Street. It’s the sort of old-world, small-town event that the whole village comes out for, with multi-generational families of Conchs (that’s the official term for someone born in Key West) lining the sidewalks to cheer and bounce along to the music. Bonus: most marchers toss handfuls of candy into the crowd, which is way more delicious than Fantasy Fest beads and you won’t even have to flash anyone for those Reese’s. Win/win!
On Sunday, Dec. 8, the Tropic Cinema, Key West Theater, Keys Choral Arts, Old Stone Methodist Church, The Studios of Key West and St. Paul’s Episcopal Church will present their third annual Eaton Street Christmas Stroll, an evening of music, theater, shopping and celebration. This innovative traveling program for all ages will feature classic Christmas carols, a live nativity, holiday-themed theatrical performances and more. The festivities begin at St. Paul’s Episcopal Church (at the corner of Duval and Eaton streets) at 4 p.m. and revelers will be able to watch a Christmas film at the Tropic Cinema, listen to live music at the Key West Theater and shop artisanal goods at the Studios of Key West.
On Saturday, Dec. 14, the sixth annual Parade of Paws & Holiday Bazaar SPCA fundraiser will commence at 10 a.m. at the Higgs Beach Dog Park. Participants work to secure pledges from their friends and family, then promenade themselves and their dogs across the beach to vie for the titles of King, Queen, Prince, Princess, Duke and Duchess. A holiday bazaar held inside the adjacent dog park will offer food vendors, crafts, gifts and entertainment. The fundraiser benefits the Animal Care Fund, which supports the SPCA’s lifesaving mission to care for our community’s homeless animals. For more information, to donate, or to register yourself and your four-legged friend, visit fkspca.org/calendar-of-events.
Those looking to experience a truly quintessential Key West holiday experience should mark their calendars for Dec. 14, then decide whether to watch the 29th Annual Lighted Boat Parade from land or sea. Both have their pros and cons, but if funds aren’t especially tight this year, book the family seats on one of the many charter boats heading out into the harbor that evening, where you’ll float amongst the 40 or so trussed up vessels, all vying for cash prizes totaling over $20,000. It’s a spectacularly fabulous, often tacky display in which the size and artistic vision of participating vessels form a massive, twinkly gradient; single-man kayaks blanketed in battery-powered icicle lights go mast to mast against massive wooden schooners, and elaborate lighted tableaus depict Santa having traded in his sleigh for a jet-ski. If you’d prefer to watch the merriment with your feet firmly planted on the ground, the best place to do so is Schooner Wharf Bar, which, in addition to formally hosting the event, ingratiates themselves among fans of limited edition beverages by adding eggnog, hot cider and some variation of spiced grog to their bar menu for the evening.
Already renowned as the only program of its kind, the Key West Sheriff’s Animal Farm, in which inmates care for seized exotic animals and livestock in a facility open to the public twice a month, becomes arguably the most unique holiday event in Key West in December. Cutting its usual bi-monthly visiting hours in half, the farm — whose non-human residents include a sloth, two llamas, rabbits, a massive tortoise, horses, hogs and more — will open its doors only once in December – from 1 to 3 p.m. on Sunday, Dec. 15. On that day, Santa himself will join the inmates and farm animals for family photographs — perhaps the only day in his career on which he’ll need to compete with a sloth for children’s attention. Having seen firsthand the undeniable charisma of Mo the sloth, it’s clear that Santa will need to bring his A-game to the jailhouse this year.
If you’re as much of a holiday shopping procrastinator as I am, you’ll be thrilled to hear that on Wednesday, Dec. 18, the Key West Art & Historical Society will host its 4th Annual Holiday Concert & Bazaar on the porch of the Custom House Museum. This super popular celebration will feature some of Key West’s finest artisans, musicians and choirs, food and libations, free entrance to the museum and a dazzling holiday light show projected onto the face of the historic building. Browse hundreds of unique gifts, get last-minute pictures with Santa, or just indulge in a nerve-calming glass of eggnog or two. Treat yourself while picking up treats for your loved ones — that’s the real magic of the holiday season.
And this is by no means an exhaustive list of everything holiday-related happening in Key West. There’s the 4th Annual FKOC Gingerbread House Auction at Sidebar on Dec. 5, First Friday Holiday Music at the Green Pineapple on Dec. 6, the Stock Island Lighted Boat Parade on Dec. 13, Christmas Rocks! at the Key West Theater on Dec. 22 and so much more. So keep your eyes and ears peeled and your hearts and minds open — we’re sure you’ll find more than your share of weird holiday magic down here. ¦