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, it has long been a come-as-you-are destination with a welcome as warm as the weather.
There’s plenty of outdoor activities to enjoy, as well as 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 from 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
Key Largo
To get to the Keys, you drive south on US 1, which leads out of Homestead. Once US 1 leaves the mainland, it transforms into the Overseas Highway, stretching all the way to Key West. The road is marked by decreasing mile markers (MM), beginning with MM 113 right out of Homestead and counting down to MM 0 in Key West.
It’s not immediately obvious that you’ve entered an island chain. Mangrove forests extend from the mainland right onto the Upper Keys, which are the northernmost islands in the chain, so you don’t initially feel like you’re driving over water (but trust us, you definitely are).
Key Largo serves as the focal point in the Upper Keys, and the main draw is John Pennekamp Coral Reef State Park. This park is unique because most of it is underwater; however, there are some lovely mangrove boardwalk trails to experience. The real attraction is one of the best-preserved coral reefs in the continental U.S., which can be accessed through snorkeling, SCUBA tours, or glass-bottom boat trips. As winter is the driest season in the Keys, you’re likely to benefit from better underwater visibility.
After an exhilarating time in the water, consider a stop at the Key Largo Conch House. Housed in a restored mansion, this restaurant serves innovative takes on fresh Florida cuisine, including crab-stuffed mahi and an exquisite lobster bisque. The wraparound porch offers outdoor dining, a luxury few places in the United States can boast.
Islamorada
As you continue southwest along the Overseas Highway, the experience starts to feel more like an Overseas Highway; causeways rise and dip amidst verdant mangrove islands dappled in teal and blue water.
The Keys consist of limestone islands fringed with mangroves, meaning there’s less sand and numerous opportunities for kayaking, fishing, diving, and wildlife observation. However, if your heart is set on tucking into that beach read under a large umbrella, make your way to Anne’s Beach, one of the best spots on Islamorada. Nestled amid mudflats and mangroves, the shallow waters, cooling breezes, and unending turquoise horizons create a wonderful place to unwind.
Robbie’s Marina is impossible to miss as you drive the length of the Keys. It’s a multi-faceted destination featuring a marina, an open-air arts and flea market, a restaurant, and a launching pad for kayakers looking to explore the mangrove islands, including the remote Lignumvitae Key. If paddling isn’t your style, guided eco-tours also depart from the marina. Visiting in winter means you avoid rough waters and the intense heat typical of a Florida summer.
Marathon
Marathon is the second-largest town in the Keys and acts as a midpoint between Key Largo and Key West. While it has tourist attractions, it remains a town for locals, or “conchs” (pronounced “konk”).
A major highlight is Sombrero Beach, which, though not a natural beach, offers a stunning stretch of soft sand ideal for seaside relaxation. Additionally, Curry Hammock State Park is the largest uninhabited land segment between here and Key Largo (spanning 1,000 acres). It’s a great spot for wandering along boardwalk trails, kayaking (boat rentals are available), and immersing yourself in old Florida wilderness.
Another noteworthy destination is the Turtle Hospital, a veterinary facility dedicated to rehabilitating injured or sick sea turtles. Visitors must attend a guided tour to explore this working animal care clinic.
If hunger strikes, don’t leave Marathon without dining at Keys Fisheries. This waterfront restaurant is the perfect place to enjoy an outdoor fish taco or a delicious lobster reuben sandwich while watching local fishermen at work on the docks.
Lower Keys
Leaving Marathon via the Seven Mile Bridge—officially 6.79 miles long—offers breathtaking views on either side of this impressive span. In the Lower Keys, the most rural islands in the archipelago, keep an eye out for the tiny Key deer, a subspecies of white-tailed deer. They are not only adorable but also protected, and speed limits are adjusted for their safety. To see them up close, visit the National Key Deer Refuge Headquarters on Big Pine and No Name keys.
The crown jewel of Keys beaches is found at Bahia Honda State Park, which looks postcard-perfect on sunny days. The soft sand and clear waters await visitors, and you can walk on an abandoned railroad that was once intended to join the islands to the mainland. The dry winter provides plenty of sunny days and clearer waters, making it a perfect time for beach trips.
Eco-conscious travelers will appreciate not just the stunning scenery and fantastic wildlife viewing opportunities but also the sustainability efforts being made in the Lower Keys. Nonprofits like Reef Relief are actively working to protect the region’s coral reefs, sandbars, creeks, and hardwood groves, which host an array of wildlife including marsh rabbits, herons, nighthawks, and mangrove cuckoos. The Looe Key National Marine Sanctuary off Big Pine Key is another great destination for exploring 18th-century shipwrecks and diverse marine life.
Key West
Key West is the literal end of the road, both literally and figuratively. Positioned closer to Havana than Miami, this island was once a haven for pirates, and it still continues to attract members of the Caribbean diaspora, eccentrics, artists, writers, and a vibrant LGBTQIA+ community.
The eastern side of Key West is home to modern businesses and larger hotels; conversely, the western half features Old Town, which is iconic Key West, filled with small local businesses that embody the city’s vibrant charm. Old Town is breathtaking—a grid of candy-colored Caribbean colonial homes shaded by banyans and palm trees. The courtyard of Blue Heaven is a wonderful spot to savor some yellowtail snapper or local spiny lobster while watching resident roosters proudly roam their territory.
Immerse yourself in local history among the faded headstones of the remarkably gothic Key West Cemetery. Later in the evening, get ready for a lively Duval Street crawl, Key West’s main thoroughfare lined with numerous bars, many featuring outdoor lounging areas. At sunset, a procession of street performers and buskers gathers to create one of the most memorable outdoor experiences in Florida at Mallory Square. The clear winter weather accentuates the sun’s descent below the horizon—a fitting finale to any journey through the Keys.
