A Crew's Guide to Exploring the Florida Keys

The Florida Keys — and most iconically Key West — have historically attracted a fascinating mix of explorers, conquistadors, pirates, treasure seekers, entrepreneurs, and writers and poets. Today, they’re a renowned international tourist destination.

Tourism and boating in the Keys is heavily concentrated in the winter months, from December through April, when the weather is cooler and calmer. Expect the usual heavy Florida humidity and heat when visiting outside these months, but also cheaper prices.

The 125-mile long chain of islands, gently arcing southwest from the Florida mainland, is best traversed through the single-lane highway, which feels more like a boat cruise than a highway. If at times slow, I personally recommend the pace to take in the stunning panoramic sea views. Unless you’re pushed for time, plan to spend around three days plodding along with ample stops. You’ll pass over 42 bridges that connect all 44 islands, including the Seven Mile Bridge. You’ll also notice along the drive the old, disused rail line that was destroyed by the devastating Labor Day hurricane in 1935.

Flying into the Keys is an equally scenic option as the flight is usually a short leg from nearby major airports into either Marathon or Key West airport. It’s also incredibly easy and cheap to fly into Miami and rent a car from there.

As you leave the Florida mainland to Key Largo, its proximity to Miami marks it as a private, high-end resort haven, with some resorts such as the Bungalows Key Largo charging as much as $1,300 a night. Venturing farther south along US 1, which is also the country’s longest north-south highway beginning at the Canadian border, you’ll find fantastic RV or camping, with the best locales in Marathon and Big Pine. You’ll have to book months in advance for the cream of the crop campgrounds, however, as most private and state park campgrounds such as Curry Hammock State Park and Big Pine Key Fishing Lodge are booked out many months in advance.

Even if not camping at these locations, it’s worth your time to detour and take a meander through the many state parks along the Keys. Long Key State Park, located roughly halfway along the Keys, and Curry Hammock State, a farther 20-minute drive south, both offer some great scenic trails and recreation areas. Bring fins and a snorkel too when you’re visiting any state park, as there are usually great conditions for some decent, accessible snorkeling all winter.

A stop in Marathon can sustain you with an iconic Lobster Reuben sandwich at the Keys Fisheries, or some great coffee and bites at the likes of Sweet Savannah’s or The Art Studio.

Arriving in Key West, you’ll be dumbfounded at the sheer spectacle this small town of only 24,000 inhabitants offers. The city is a focal point for much of the Florida Keys’ established personality, inviting the likes of Ernest Hemingway, and past presidents Harry Truman and John Kennedy to live and spend time here.

If you came to party, you’ll find it on Duval Street, where the time to let loose is seemingly a 24-hour affair. Willie T’s and General Horseplay both have a great crowd and usually decent live music; however, I’ve sure you could find your own favorites among the dozens.

Try and steer clear of the cruise ship crowd trappings of T-shirt shops and chain-brand shops along Mallory Square unless you’re there to witness an incredible sunset, and go check out Fort Zachary Taylor, the island’s beautiful state park, the Key West Butterfly Conservatory, or make a day (or overnight, there’s camping!) trip to the Dry Tortugas, accessible via the Yankee Freedom III ferry company. And if you’re so inclined to the quieter side of island life, there’s an absolutely fantastic local yoga joint called the Key West Yoga Sanctuary and nearby book shop, Books & Books of Key West. You’ll be more likely to meet and talk with some true locals here.

All in all, the Florida Keys is a fascinating gateway to island life, a distinct concentration of the Floridian laidback way with a special kind of quirkiness.

This article originally ran in the November 2020 issue of Dockwalk.