People come to Florida for many reasons – warm weather, good vibes, and ecosystems like no other chief among them. Another major motivation, for some at least: the desire to be in a place without rules.
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, its 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.
For the latest protocols on health & safety in The Florida Keys, please visit fla-keys.com
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. Since winter is the driest time of year in the Keys, that (generally) means you’ll have better visibility underwater.
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.
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, restaurant, and launching point for kayakers who want to paddle around the mangrove islands like the abandoned Lignumvitae Key. 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.
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.
If you’re feeling peckish, don’t leave Marathon without grabbing a meal at Keys Fisheries. This restaurant, which overlooks a working waterfront, is a lovely spot for an outdoors fish taco or lobster reuben sandwich, all enjoyed as you watch fishermen clean out the next customer’s order on the docks.
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. Seriously, keep an eye out! 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 measure taken in the Lower Keys. Nonprofits like Reef Relief work to protect the region’s coral reefs, sandbars, creeks, and 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 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.
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. Clear winter weather accentuates the sun as it dips below the water, a fitting finale to a Keys road trip.
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