As temperatures in North America drop, imagine waving goodbye to your snow shovel and rain boots and saying hello to sunny skies, coral reefs, and pastel-colored cottages.
That’s what you’ll find in Key West, the last-pit-stop island at the southern end of the Florida Keys (and the southernmost point in the continental United States). This is the spot where the Atlantic Ocean meets the Gulf of Mexico, and the water is as astonishing shade of blue.
Pack your shorts and polo shirts. With an average daily wintertime high of 78 degrees, it’s more than warm enough to swim in the city’s numerous heated pools or lounge in the sun, but just cool enough that the ice in your margarita won’t melt too fast.
Of course, you want to be prepared for all of this ideal relaxation.
Here are a few pointers and then some:
Pick the right pool
The majority of hotels and guesthouses in Key West offer beautiful pools for everyone’s favorite vacation activity: laying in the sun, catching up on your reading, and Instagramming all of it for your friends back home.
Key West is one of the gay-friendliest towns in the world, and several hotels that cater to LGBTQ are known for their pool party scenes. Island House and Equator Resort are clothing-optional guesthouses that cater to gay men, and Bourbon Street Pub, one of the most popular bars on Duval Street, has a guesthouse on property, New Orleans House, with a rollicking pool. All three pools have access to the hotel bars, so you can mouth that favorite line you’ve been rehearsing all year: “Cabana boy! I’m ready for another.”
Related: Where to stay in Key West? Pick a place with a nice pool
Look your best
The standard for swimwear in Key West is simple: the smaller, the better, and no worries about your body type. Many guests go au naturel, but if you’re shy (which we think is adorbs, by the way), don’t worry: At every clothing-optional pool, you’ll see guests who keep their swimsuits on. Looking for a new swimsuit? Check out the selection at Graffiti on Duval Street, the main shopping and dining strip.
Related: Steve Grand wants you to feel proud when you wear your Speedo in Key West
With weather this temperate — pleasant, not sweltering — it’s easy to forget the sunscreen. But winter or not, you are officially in the tropics, and the rays down here are strong. Because of concern for its famous coral reefs, Key West is the first city in Florida to ban the sale of sunscreens that contain oxybenzone and octinoxate, two of the chemicals that damage fragile coral ecosystems.
Most pharmacies in town carry reef-safe sunscreen, including the Walgreens on Duval, so no need to worrying about packing it.
Do the foodie thing
Laid-back as it is, Key West has over the last several years developed a serious foodie scene. Eating out is part of the culture here, and most nights you’ll find locals and visitors alike dining side by side at some of the city’s finest restaurants.
The glamorous resorts on Key West’s southern shore have highly rated restaurants with locally sourced seafood. At Sun Sun in the Casa Marina resort, for instance, start with Bahamian conch fritters before moving on to coconut-poached lobster. The more casual cafe at Island House is where you can order tuna tataki and a juicy prime rib poolside—or if you’re just starting out the day, go in for their popular breakfast.
The elegant and contemporary Marquesa Hotel boasts one of the finest restaurants in Florida, Cafe Marquesa, which serves New American dishes (think crisp yellowtail snapper with Parmesan grits, or Atlantic swordfish served alongsisde risotto) that changes with the season. The restaurant at La Te Da, a hotel on Duval Street, has a strong fan base of regulars who return for the baked oysters, icy cocktails, and shows in the cabaret lounge.
Related: Walnut and pistachio tacos, ceviche, and caviar: an insider’s guide to restaurants in Key West, by drag legend Randy Roberts
Pace yourself, though, because you’re in Key West, which means Key Lime pie is a must. One of our favorite versions, packed high with meringue, can be found at Blue Heaven.
Wintertime blues? We don’t think so.