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 in late November 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:
The holiday giving season kicks off strong on Sunday, Dec. 2, with the Holiday Bazaar to benefit May Sands Montessori School from noon to 6 p.m. at First Flight Restaurant & Brewery (301 Whitehead St.). This free event (until you realize you’ve spent all your rent money on unique Christmas gifts) will feature Key West’s finest artisans, festive music and delectable desserts and drinks to help evoke the spirit of the season. The garden at First Flight will be transformed into a winter wonderland, complete with Key West’s version of “snow” and the festive sounds of one of our many talented local DJs, who will be spinning all of your holiday favorites (DMX’s version of “Rudolph the Red- Nosed Reindeer,” anyone?). All proceeds from the bar will benefit May Sands Montessori School and you’ll sleep easy knowing you’re doing your part to “shop local” when you buy from the local artisans on hand.
This may come as a surprise, but Christmas in Key West isn’t complete without a parade or two. The Lighted Bike Parade kicks off at 7 p.m. on Wednesday, Dec. 5, where a seemingly endless number of bicycles careen through town in a riot of colorful LEDs and glow sticks and maybe an adult beverage or two at the after-party at Mary Ellen’s Bar (hence the careening). Outof towners looking to participate (and you should — it’s a truly magical feeling to find yourself, midweek, trying to keep your balance between tandem bicycles lit up like Christmas trees in the middle of the street) should rent their bicycles a day or two early. There are plenty of rental companies to go around, but if you haven’t been on a bicycle in over a decade, there’s no shame in renting an adult tricycle. Seriously, they’re great — all the wind in your hair, none of the horrifying realization that that last glass of spiked eggnog might have put the nail in your balance’s coffin.
Dec. 7 marks the beginning of this year’s “Nutcracker Key West,” a tropical spin on the classic ballet, produced biennially by the tireless Joyce Stahl. This only-in-Key West production comes complete with chickens, roosters, anemones and, yes, even a conch-headed nutcracker. So, put on your holiday best and pull out your sugarplums for this ethereal two-act holiday reverie cast primarily with local children and an international ballet star or two. The show, hosted by the Tennessee Williams Theater (5901 College Rd., Stock Island), runs through Dec. 16. Tickets can be purchased online at keystix.ticketforce.com/ or over the phone at 305-295-7676.
Dec. 7 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 Key West Butterfly & Nature Conservatory on Dec. 7 and the Hemingway Rum Co. Distillery, Old Town Manor, Wicker Guesthouse, The Mermaid & The Alligator, Suite Dreams Inn and Santa Maria Suites Resort on Dec. 14 — will deliver an eyewatering display and spread of festive treats for attendees, who are carted from place to place via trolley from 6 to 8 p.m. on both nights. Tickets can — and should — be purchased ahead of time at https:// keystix.ticketforce.com/.
Those in town on Friday, Dec. 7, with pets should trek over to the end of William Street (on the Schooner Wharf side) to the Pet Pictures with Santa event at 6 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 leap out of Santa’s lap, did Christmas even really happen?
Because one parade is never enough down here, on Saturday, Dec. 8, the annual family-friendly Key West 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 multigenerational 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. The candy is way more delicious than Fantasy Fest beads, AND you don’t have to flash anyone for those Reese’s. Win/win!
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 what could be the most unique holiday event in Key West in December. Cutting its usual visiting hours in half, the farm — whose non-human residents include a sloth, two llamas, rabbits, snakes, horses, hogs and more — will open its doors only once in December, from 1-3 p.m. Sunday, Dec. 9. Santa will join the inmates and farm animals for family photographs (having seen firsthand the undeniable charisma of Mo the sloth, I can promise Santa needs to bring his A-game to the jailhouse this year).
On Sunday night, the Tropic Cinema, Key West Theater, Key West United Methodist Church, The Studios of Key West and St. Paul’s Episcopal Church present the second annual Eaton Street Christmas Stroll, an evening of music, theater, shopping and celebration. This innovative traveling program for all ages features classic Christmas carols, a live nativity, holidaythemed theatrical performances and more. The festivities begin at 4 p.m. at St. Paul’s Episcopal Church at the corner of Duval and Eaton streets. 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. 15, the fifth annual Parade of Paws & Holiday Bazaar SPCA fundraiser begins at 10 a.m. on Higgs Beach. 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 offers 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 for the quintessential Key West holiday experience should mark their calendars for Dec. 15, then decide whether to watch the 28th 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 more than $20,000 in cash prizes.
The boat parade is 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 batterypowered 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 prefer to watch the merriment with your feet firmly planted on the ground, the best place to do so is Schooner Warf Bar which, in addition to formally hosting the event, ingratiates itself among fans of limited-edition beverages by adding eggnog, hot cider and some variation of spiced grog to the menu for the evening.
This is by no means an exhaustive list of everything holiday-related happening in Key West.
There’s the Stock Island Lighted Boat Parade on Dec. 7, the Island Greater Goods Market at Lost Kitchen Supper Club and “Landon’s Dysfunctional Family Christmas” at First Flight Island Restaurant & Brewery on Dec. 9, the third annual FKOC Gingerbread House Auction at Sidebar on Dec. 12, “Christmas Rocks!” at the Key West Theater on Dec. 15 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. ¦