If you are inclined to think the Sunshine State is the ideal place to kick back and be yourself, that’s an even truer sentiment in the Florida Keys. Disconnected from the mainland and floating like a string of sandy pearls descending southwest from Homestead, it has long been a come-as-you-are destination with a welcome as warm as the weather.
There’s plenty of outdoors stuff to do, al fresco dining options abound, and did we mention that the temperature averages around 78 degrees year-round? Winters here are not only warm relative to the rest of the country, they’re also the driest time of year in South Florida, so you don’t have to worry about sudden squalls or hurricanes.
In other words, it’s just a different vibe in the Florida Keys. So this winter, while everyone else is suffering gray skies or seeking snow-covered holidays, opt for something different yourself. Keep reading as we explore what to do through the Florida Keys throughout winter.
For the latest protocols on health & safety in The Florida Keys, please visit fla-keys.com
Florida Keys winter weather
Can you swim in the Florida Keys in December? Yes! Water temperatures remain mild, even as daytime temperatures can sometimes dip. The average daily high ranges from 74 to 76 °F throughout the winter, though the daily average low dips into the mid-60s. If the air temperature is low, wearing a wetsuit will allow you to swim, dive, snorkel and paddleboard comfortably this season. Don’t worry about buying your own – many local snorkel and dive shops rent wet suits.
Key Largo
You get to the Keys by driving south, and south, and more south still, on US 1 out of Homestead. Once US 1 leaves the Florida mainland, it becomes the Overseas Highway, which stretches to Key West. The length of the road is marked by decreasing mile markers (MM), starting with MM 113 right out of Homestead, and ticking down to MM 0 in Key West.
With that said, it’s not immediately obvious you’ve entered an island chain. Mangrove forests extend from the mainland right onto the Upper Keys, the northernmost islands in the chain, so you don’t initially get the sense of driving over water (but trust us, you are).
Key Largo is the center of activity in the Upper Keys, and the main draw is John Pennekamp Coral Reef State Park. As parks go, this one is unique in that most of it is located underwater, although there are some nice mangrove boardwalk trails to enjoy. But the real attraction is one of the best-preserved coral reefs in the Lower 48 United States; this underwater wonderland can be accessed via snorkeling and SCUBA tours, or glass-bottom boat trips. One of the underwater park’s highlights is the Christ of the Abyss, a sunken statue of Jesus that attracts divers from all around the world.
Since winter is the driest time of year in the Keys, that (generally) means you’ll have better visibility underwater. This makes this season one of the best times to visit the Florida Keys if you plan to dive. December is a good time for snorkeling or diving in the Florida Keys because the water temperatures stay in the low 70s °F this time of year, making for comfortable diving and snorkeling as long as you have the right gear.
If you prefer to stay above the waves, another must-do is a cruise on the African Queen. This historic steamboat was featured in the film of the same name, which debuted in 1951 and starred Katharine Hepburn and Humphrey Bogart. Daily cruises take you up the Port Largo Canals and out to sea before turning back.
After wearing yourself out in the water, consider stopping into the Key Largo Conch House. This restaurant, housed in a restored mansion, serves innovative takes on fresh Florida cuisine, serving crab-stuffed mahi and a mean lobster bisque. There’s a wraparound porch for outdoor dining, which is available year-round – a luxury few places in the US can boast.
Islamorada
As you proceed southwest along the Overseas Highway it starts to really feel like an Overseas Highway; causeways rise and dip amidst green mangrove islands that dapple the teal and blue water.
The Keys are made up of limestone islands fringed with mangroves, meaning a little less sand and a lot more chances for kayaking, fishing, diving, and wildlife viewing. But if you have your heart set on tucking to that beach read under a big umbrella, head to Anne’s Beach – one of the best on Islamorada. Tucked away amid mudflats and mangroves the shallow water, cooling breezes, and unending turquoise horizons make for a nice place to relax.
You can’t miss Robbie’s Marina as you drive the length of the Keys. It’s hard to find one descriptor for this place; it is a marina, an open-air arts and flea market, a restaurant and a launching point for kayakers who want to paddle around the mangrove islands like the abandoned Lignumvitae Key. But to find the marina’s most popular attraction, walk out the back of the restaurant onto the dock. Here, you can purchase fish to feed the giant tarpon that gather beneath the docks. Watch your fingers – these massive fish can reach up to eight feet long and weigh over 300 pounds. It’s also not unusual to see manatees here, especially during the winter months.
If you’re not into paddling yourself, you can also book onto a guided eco-tour, which depart from the marina. Going in winter means you won’t have to put up with rough water, or the intense heat of a Florida summer.
Speaking of fish, Islamorada is known as a sport fishing capital of the world. If you don’t have your own boat, book one of the many charters available on the key and elsewhere throughout the Florida Keys. Alongside diving, fishing is one of the Florida Keys’ top attractions. If you need to pick up some tackle, Islamorada is home to a Bass Pro Shops that sells everything from tackle to outdoor clothing and even has an overwater restaurant in the back.
Marathon
The second-largest town in the Keys, and the rough halfway point between Key Largo and Key West, is Marathon. While Marathon has its own tourist attractions, it is also very much a town for Keys locals, who are also known as “conchs” (pronounced “konk”).
One of the biggest draws here is Sombrero Beach; while this isn’t a natural beach, it is a very pretty stretch of buttery sand that ticks all the boxes when it comes to seaside relaxation. Curry Hammock State Park is the largest parcel of uninhabited land between here and Key Largo (1000 acres). It’s a great spot for wandering boardwalk trails, kayaking (you can rent boats here), and just generally getting gently lost in old Florida wilderness.
Also of note is the Turtle Hospital, a working animal care clinic that rehabilitates injured or sick sea turtles. Because this is an actual veterinary hospital, you must visit on a guided tour.
Don’t leave Marathon without grabbing a meal at Keys Fisheries. This restaurant, which overlooks a working waterfront, is a lovely spot for an outdoor fish taco or lobster reuben sandwich, all enjoyed as you watch fishermen clean out the next customer’s order on the docks.
Lower Keys
You’ll leave Marathon via the Seven Mile Bridge, which is, well, a very long bridge (6.79 miles long, if you’re nitpicking). The views on either side of this span are suitably breathtaking. In the Lower Keys – the most rural islands in the archipelago – keep an eye out for tiny Key deer, a subspecies of white-tailed deer. Key deer aren’t just cute – they’re protected and speed limits are reduced for their safety. If you want to get a closer look, head to the National Key Deer Refuge Headquarters on Big Pine and No Name keys.
The crown jewel of Keys beaches can be found at Bahia Honda State Park, postcard-perfect on a sunny day. The sand is fine and the water is clear and, as a bonus, you can go for a walk on a piece of abandoned railroad that was supposed to unite the islands with the mainland. The dry winter makes for plenty of sunny days and clear(er) water – all good conditions for a beach trip.
Eco-minded travelers will be thrilled not only with the scenery and wildlife viewing opportunities, but also with sustainability measures taken in the Lower Keys. Nonprofits like Reef Relief work to protect the region’s coral reefs, sandbars, creeksand hardwood groves that are flush with marsh rabbits, herons, nighthawks and mangrove cuckoos. The Looe Key National Marine Sanctuary off Big Pine Key is a great place to take in 18th century shipwrecks and ocean life alike.
Key West
Key West is the end of the road, literally and figuratively. Closer to Havana than it is to Miami, this was once a port for pirates and today it continues to attract members of the Caribbean diaspora, eccentrics, artists, writers and a large, influential LGBTQIA+ population.
Winter is one of the best times to visit Florida for great weather. Thanks to the constant sea breeze, the Florida Keys tend to be cooler than other parts of Florida during the summer – though sweltering heat on Duval Street is the norm. With narrow streets and stone buildings capturing the heat and blocking the breeze, not to mention crowds of people shopping and enjoying the many bars and restaurants, summer can get pretty sweaty in downtown Key West. December offers a welcome reprieve.
However, the best time to visit Key West depends on how you’d like to spend your time. If you plan to spend a lot of time in the water, you may still want to consider a visit sometime between late spring and early fall. But if you’re planning to enjoy the shopping, dining and sightseeing that Key West offers, winter is far more comfortable.
The eastern half of Key West is mainly modern businesses and larger hotels, while the western half includes Old Town, which is iconic Key West and flush with small local businesses that are an irreplaceable part of the city’s vibrant charm. Old Town is simply gorgeous – a grid of candy-colored Caribbean colonial homes all shaded by banyans and palm trees. The courtyard of Blue Heaven is a wonderful spot to grab some yellowtail snapper or local spiny lobster while you watch resident roosters (literally) rule their roost.
Soak up local history amidst the faded headstones of the impressively gothic Key West Cemetery. Then, come the evening, prepare yourself for a Duval crawl along Duval Street, Key West’s main drag. There are tons of bars here, and even pre-pandemic, they all had outdoor lounging spaces. At sunset, a gaggle of street performers and buskers still put on one of the greatest regular outdoor performances in Florida at Mallory Square. This popular nightly festival is one of the best free things to do in the Florida Keys. Clear winter weather accentuates the sun as it dips below the water, a fitting finale to a Keys road trip.
Plus, from the decorations to the many special events held throughout the season, Christmas in Key West is truly unique. Many businesses on Duval Street put up decorations, turning the historic shopping and dining district into a tropical wonderland. The city puts on many holiday events, including a Christmas parade.
Key West is also home to some of the best accommodation options in December in the Florida Keys. On this key, you’ll find endless hotels and motels, home rentals and campgrounds where you can pitch a tent or park your RV. There are plenty of options for every travel group and budget.
Winter events in the Florida Keys
If you’re trying to decide when in December to plan your visit to the Florida Keys, there are a few free events and festivals held in the Keys this season that you should know about.
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The Key West Christmas Parade is a tropical spectacle that winds down Duval Street and through Old Town.
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The Schooner Wharf Bar & Galley Lighted Boat Parade takes place on the water, with dozens of sailboats and other ships decorating their sails and booms with lights and holiday decor.
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Further up the Keys, Light Up Key Largo brings a variety of Christmas festivities, from a holiday train to Santa Claus to a variety of vendors together for a day of fun.
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