While one could make the case that there’s technically no bad time to travel to Key West, a mid-December week of persistent freezing rain in the northeast provided an ideal opportunity to experience the Florida island. The bounties of the island are certainly no well-guarded secret, but somehow it managed to both defy and reaffirm its reputation as an oasis of bacchanalia, with an assist from history, culinary revelations and natural wonders.
The overabundance of Christmas decorations throughout — elaborately appointed two-story verandas, decked out palm trees, carols playing on speakers at many of the open air restaurants along the water — all conspired to enhance the alternate dimension experience. All in all, Key West in December was something like visiting a mix of Cape Cod grafted together with New Orleans, only with more water sports.
Here are five spots to consider for planning your own holiday getaway, whether you’re going for a last-minute vacation this year or planning ahead for next.
Where to stay
Owing to strict laws about where new construction can take place on an island already overflowing with hotels, resorts and bars, the Marker Waterfront Resort is the first new hotel built in Old Town Key West in 20 years. The 96-room luxury hotel, situated just off the crowded boardwalk along the marina, brings together a sophisticated Caribbean style feel with a clean and modern design replete with a bounty of local artists’ works.
All of the rooms, each with their own balcony, come with a view of one of the three tranquil pools at the resort or the busting marina. And while there is an upbeat energy to the open-air restaurant and bar Cero Bodega, it’s a more refined experience than you’ll find most elsewhere nearby, where debauching tends to be the primary concern. The low season rates start at $229; the high season is $449.
Where to drink like a local
You’ll find no shortage of bars across the island filled with sunburnt revelers and aggressively relaxed locals, many of whom have turned the music of Jimmy Buffet into a lifestyle reality, and plenty of disposable tourist trap bars. But for local character, the Green Parrot is your best bet. The late 19th century building, once a grocery, then a naval bar, offers up a panoply of the type of beach bums, hippies and seamen you probably have in mind when you think of Key West. With people drinking outside on the street and smoking inside the bar, all while dancing unselfconsciously to feel-good live bands, I couldn’t help but feel like I was in bizarro Boston or New York.
Where to drink cocktails
While there are plenty of fine restaurants on the island, the drinking culture tends to skew more towards beer and frozen margarita. One glaring, and brilliant, exception is The Other Side. Taking up one side of a centuries-old residence (so haunted they used to run ghost tours in it), this is the cutting edge of Key West’s cocktail scene, perfect for urbanites needing a respite from all of the beach life transpiring outside.
Dimly lit, with a throwback hip hop soundtrack, the bartenders here dash between the respected classics you’ll see coming off speakeasy bars in New York City along with showmanship style recipes, like a tequila and Ancho Reyes recipe that turns to liquid flame as it’s being mixed. After drinks walk up Duvall Street for refined cuisine at Nine One Five.
Where to stroll
Duvall Street is the main commercial thoroughfare. You’ll find booming open-air clubs, tattoo shops, art galleries, sausage stands, literal dude with parrots on their head, touristy bric a brac, cigar shops, Darth Vader playing a banjo, karaoke, drag shows, jazz bars and more art galleries.
Where to have an adventure on the water
Fury Water Adventures has a breadth of options for getting out on the water and staying active, including glass-bottom boat tours, parasailing and jet-skiing. A snorkeling adventure out along the choral reef provided beautiful vistas under the sea, and plenty of exercise swimming for my life from barracudas and jelly fish. For a more relaxing voyage, take a trip on the the Schooner Hindu for a breathtaking sunset sail.