A Key West Holiday
One of the most iconic American escapes is to Key West - and during the holidays, it is perhaps one of the greatest escapes that you could attempt. Trade endless snow for soft beach sand; cold grey skies for bright sunshine; and paralyzing cold for tropical breezes. Doesn’t that sound like a much better place to spend your holiday? Well, if you need further convincing, read on…
Boats, Lights, Magic!
The waterfront of Key West serves as the stage for several of the island’s most iconic holiday celebrations.
A Key West tradition is the Lighted Boat Parade in mid December, when dozens of beautiful vessels sail beneath the moonlight in the waters of the Key West Bight and Harbor. Each boat is allowed to choose a theme and is judged on their creativity. Want to be a part of the action? There are several boat rental companies that will be participating in the parade, and they want to offer you a seat aboard their ship. Fury Key West wants you to join in on the fun with champagne, full bar, delicious appetizers like conch fritters and smoked fish dip, and live music all included in your ticket price.
furycat.com/key-west
The second event is New Year's Eve at Schooner Wharf, which of course happens on the 31st, and is a beloved tradition of the island. Pop some champagne bottles as you watch the crew members of the Schooner Wharf Bar perform the annual “Lowering of the Pirate Wench,” in which a fair maiden climbs down a ship’s mast to mark the countdown to New Year’s, and at midnight cannons will ring (or “boom”) in the new year. Schooner Wharf has complimentary hats, party favors and horns for everyone to feel festive while enjoying holiday drink specials and live music throughout the day and night.
schoonerwharf.com
Festive Tours
As an island already full of colorful and eclectic sights, Key West is always a beautiful and interesting place to take a tour; but the holidays add a little extra magic to your sightseeing adventures.
While folks up north have to get around in a sleigh, you’ll be seeing the town aboard a trolley - when you travel with Old Town Trolley Tours, that is! Their already upbeat tour is made even more cheerful by the trolley’s colorful lights and special nighttime tours in which you can see the beautiful lighted decor all around the island. During their Holiday Lights & Sights Tour, you can sip on cider and munch on cookies before heading off to see many bedazzled homes, hotels, and other attractions. A popular choice for visitors with children, the Conch Tour Train has delighted young and old for many years. Their annual holiday lights tour begins with treats and continues with an hour-long tour of beautiful lighted homes (including the island’s most elaborately decorated house!) and warms the heart with caroling.
trolleytours.com/key-west
conchtourtrain.com
The Little White House is a living museum for visitors to literally live in a part of history, as it has been a presidential retreat since Harry Truman spent a large amount of his presidency in this beautifully restored home, and has continued to be an escape for presidents to this day. Tours are offered regularly, but it is the V.I.P. holiday tours that are a bonus; during such a tour, you will tour the incredible house and indulge in champagne, hot chocolate, treats and more. Visit the gift shop afterward to pick up some presidential postcards, as well as gorgeous White House Collector ornaments that are prefect for stocking stuffers.
trumanlittlewhitehouse.com
Key West may be in the tropics, but that hasn’t stopped local inns from decorating like they’re part of the North Pole - indeed, Santa will have no trouble finding these inns on his gift-drop route. Presented by the Key West Innkeepers Association, the tour of these Key West inns see you visiting each lovely location via trolley, with innkeepers offering insights into the location and its history, and they welcome you inside for libations and light appetizers. The rest of the tour is up to you as it is primarily self-guided. Tickets can be purchased at
keystix.com.
Holiday Drama
What would the holidays be without a little drama? Well, in Key West, you can experience lots of drama - and none of it at the expense of your nerves.
Embark on the Eaton Street Stroll for more cheer than drama; during this relatively new holiday tradition, several Eaton Street venues will each host a short Christmas-themed performance with caroling as you walk from presentation to presentation. In previous years there have been showings of "Charlie Brown Christmas (1965)” as well as choir performances and live music. Tickets for the event can be purchased at
tropiccinema.com.
We are most all familiar with the dramatic ballet Nutcracker, but each year this island community offers a little twist with Nutcracker Key West. This particular production features Key West’s tropical environment and rich cultural history, with new sets to delight the eyes, costumes to take your breath away, and props that spark laughter. The production will take place at the Tennessee Williams Theatre, and is put on by the island’s own community for an extra ounce of heart put into each performance.
nutcrackerkeywest.com
Vroom Vroom!
Add a little pump of excitement to your holiday getaway with Key West’s motorsport - on land or water!
As one of the most iconic places to which you can road trip, it makes sense that there is a beautiful classic car show happening during the holiday season. Check out the main parking lot on Caroline and Margaret Street for an event put on by the Southernmost Car Club. This FREE event collects unwrapped toys for the Domestic Abuse Shelter, and your thank-you for donating is to see mouthwatering classic cars decorated to the hilt (or the fender) for the holidays.
thesouthernmostcarclub.com
Fast engines are not just found on land - indeed, The Florida Powerboat Club wishes you happy holidays and urges you to add a little adrenaline pump to your trip with a powerboat rental. Spencer’s Boat Rental and Boatyard, located at Garrison Bight in Key West, is one of the top boatyards on the island, with a wide range of fishing, party and speedboats for all group sizes and budgets.
flpowerboat.com
spencersboatyard.com
Twice the Celebration
If you’re lucky enough to be spending both Christmas and New Year’s in Key West, then you’ll have twice the amount of holiday magic to enjoy!
Starting in November, Key West’s waterfront is transformed with their annual “Bight Before Christmas” celebration - a clever wordplay but an even more clever event, as the festivities along the historic seaport (or “bight”) include the Fishing Buoy Christmas Tree, a real pine Nautical Christmas Tree and the Lobster Trap Christmas Tree all honoring the Maritime History of Key West. The Nautical Harbor Walk of Lights is enchanting and romantic, and offers the perfect evening stroll to visit the shops along the waterfront, or perhaps dine at a local restaurant. Throughout December, the Bight plays host to a variety of events like holiday musical performances, pet photos with Santa, a violin charity jam, a classic car show and the Lighted Boat Parade.
keywesthistoricseaport.com
keywestchristmas.org
Arguably one of the most iconic South Florida events to ring in the New Year, the annual Key West New Year’s Even Celebration is definitely one of the most fun events you’ll ever attend. Join other revelers in several spots throughout town for very different takes on New Years Eve countdowns… In front of the Bourbon Street Pub a disco party goes non-stop with drag queens entertaining on an outdoor stage. At midnight, Sushi, the diva of drag and dressed in a glittering ball gown, descends from the top balcony inside a red eight-foot-long high heel. Just down the block at the famous Sloppy Joe’s Bar, you can watch a giant manmade conch shell descend from the roof while you sip on a brew. Ocean Key Resort offers a milder family-friendly celebration with the countdown featuring a Key lime wedge being dropped into a margarita.
bourbonstpub.com
sloppyjoes.com
oceankey.com
You couldn’t possibly need more convincing to spend your holiday - or holidays plural - in Key West. So what’re you waiting for? Pack your bags, put on your sunscreen, and bring an extra suitcase for all the presents you’ll bring back.
