WHEN MOST PEOPLE THINK OF THE holidays, it’s not typically visions of palm trees and sandy beaches that dance through their heads. Alas, “Key West” and “White Christmas” are kind of polar opposites (no Santa-inspired pun intended). But while our friends up north are dreaming of sugarplums and freezing their bundled up tushies off, we here in the Florida Keys will be celebrating the season our way — with Conch Train 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 words to Bing Crosby’s greatest holiday hits) and parades and parties galore, sans the winter coats and frigid temps 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 powder 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 laidback options for those looking to experience the holidays island style.
When the weather takes a turn for the chilly (and for the record, that’s anything under 75 degrees) 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 on the front lawn. Electricity bills begin to skyrocket as the competition for best-dressed house takes off across town. Conch Train tours start offering special cookie-and-cider evening rides through Old 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-heavy drink specials. Here’s what’s on deck:
The holiday giving season kicks off strong on Dec. 1 with the Holiday Bazaar to benefit May Sands Montessori School from 4 p.m. to 9 p.m. at First Flight Restaurant & Brewery at 301 Whitehead St. This free event (until you realized you’ve spent all your rent money on 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 DJ Chaka, 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.
That same evening, 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 at 6 p.m., hosted by local veterinary group All Animal Clinic.
On Dec. 2, 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 multi-generational families of Conchs (that’s 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. You won’t even have to flash anyone for those Reese’s. Win/win!
Since one parade is never enough in Key West, the Lighted Bike Parade kicks off at 5 p.m. the following Wednesday, Dec. 6. A seemingly endless number of bicycles careens through town in a riot of colorful LEDs and glow sticks and maybe an adult beverage or two (hence the careening). Out-of-towners should participate. 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. They also 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. 8 signals the return of the Holiday Historic Inn Tour, a favorite among those fans of Key West’s historic architecture. This year’s participating inns — La Te Da Hotel, The Wicker Guesthouse, Weatherstation Inn, Southwinds Motel, La Mer and Dewey House Bed & Breakfast on Dec. 8 and The Avalon Bed & Breakfast Hotel, The Mermaid & The Alligator, The Gardens Hotel, Island City House Hotel and the Key West Butterfly & Nature Conservatory on Dec. 15 — will deliver an eye-watering 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. The following day, Dec. 9, the fourth annual Parade of Paws SPCA fundraiser will commence 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 will offer food vendors, crafts, gifts and entertainment.
Those looking to experience a truly quintessential Key West holiday experience should mark their calendars for Dec. 9, then decide whether to watch the 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, where you’ll float amongst the 40 or so decorated 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 forms 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 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 its bar menu for the evening.
On Dec. 10 the Key West Theater, Key West United Methodist Church and St. Paul’s Episcopal Church will present their Eaton Street Christmas Stroll, an evening of music, theater 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 5 p.m. and will travel down Eaton to the United Methodist Church, finishing at the Key West Theater.
Already renowned as the only program of its kind, the Key West Sheriff’s Animal Farm, where 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, snakes, horses, hogs and more — will open its doors from 1-3 p.m. on Sunday, Dec. 10, only. On that day, Santa himself will join the inmates and farm animals for family photographs — perhaps the only day in his career in 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.
Dec. 14 marks the beginning of this year’s Key West Burlesque holiday show, aptly titled “Sugar Rum Cherry: A Nutcracker.” Put on your stockings and pull out your sugarplums for this naughty two-act holiday reverie featuring local favorite burlesque starlets Cheeky Derrière and Moana Amour, and international superstars Aurora Natrix and Jenna Beth as they visit the land of licentious libations. The show, hosted by the Key West Theater (512 Eaton St.), begins at 8 p.m. and tickets can be purchased online at www.thekeywesttheater.com or over the phone at 305-985-0433. ¦