This historic 113-mile stretch of U.S. 1 from the edge of mainland Florida to Key West is classic sun-kissed Americana. Tiki bars, fish shacks, and kitschy tourist traps line the roadway, which snakes through lush mangroves and over electric blue waters. After the Labor Day hurricane of 1935 destroyed Florida businessman Henry Flagler’s Overseas Railroad, which provided service all the way to Key West, construction began on the current highway that replaced it. Completed in 1938, the highway is an engineering marvel with forty-two bridges that string together coral and limestone islets and islands with whimsical names like Knockemdown, Fiesta, and Shark. The full trip takes about four hours, but what’s your hurry? Things move slower down here—the speed limit is just forty-five miles per hour along most of the route—so crank up the Jimmy Buffett tunes, roll the windows down (or, better yet, pop the top), and follow our long-weekend itinerary.
Follow U.S. 1 south from Miami. Skirting the Everglades, you’ll hit Key Largo; instead of hanging a right and continuing toward Key West, detour to Card Sound Road for a Florida lunch of conch fritters and grouper sandwiches at Alabama Jack’s. With its anything-goes Old Florida atmosphere, the unassuming seafood joint and waterfront bar, founded in 1947, is the perfect Keys introduction. Once you’re sufficiently full (and relaxed), head to John Pennekamp Coral Reef State Park, the nation’s first underwater park. The Keys are home to the only living coral reef in North America and at John Pennekamp, you can explore seventy-nautical-square-miles. Snorkeling and diving trips are available through the park as well as private charter companies out of Key Largo. If you just want to swim and sunbathe for a couple hours, walk to Cannon Beach—named for the remnants of a Spanish shipwreck resting a hundred or so yards off the shore. When you’re ready to hit the road again, fortify yourself with a slice of tart, scratch-made key lime pie at Mrs. Mac’s Kitchen.
Continue along U.S. 1 for another twenty-six miles to Islamorada—the halfway point between Miami and Key West, which makes it an ideal place to pause for a day or two. Reserve a room (in advance) at the Moorings Village, the lush setting of Netflix’s Emmy award–winning drama Bloodline. A former coconut plantation, the eighteen-acre, beachfront resort offers one-, two-, and three- bedroom cottages. Take one of the resort’s paddleboards for a late-afternoon spin or hop on a beach cruiser and pedal up the street to the Florida Keys Brewing Co. for happy hour. For dinner, you’ll find island fare with a fancy French twist at Pierre’s—not to mention, the west-facing beachfront verandas make a prime sunset perch.
Dubbed the sport fishing capital of the world, Islamorada has long attracted anglers chasing tarpon, snapper, mahi mahi, marlin, and more. After breakfast of fish and grits at the Hungry Tarpon head over to Bud N’ Mary’s, where the Stanczyk family has manned dock lines for nearly fourty years and will happily hook you up with a half- or full- day charter. Once you’re back dockside, cart your catch next door to Lazy Day’s, where chef Lupe Ledesma will prepare the fish for dinner—grilled, fried, blackened, or broiled.
Marathon and the Lower Keys
Get an early start the next morning. Thirty-five miles further south on U.S. 1, park your car in the lot at mile marker 47 and walk the stunning 2.2 miles down a section of Old Seven Mile Bridge to Pigeon Key. The bridge—closed for repairs until April—is a decommissioned expanse of Flagler’s railroad. One of the prettiest spots in the Sunshine State, the path remains popular with cyclists, fishermen, and tourists alike. See if you can spot sharks circling the pilings in the clear blue water below. Hungry? Head back into Marathon. Through May 15, you can order a mess of meaty stone crab claws (with drawn butter for dipping) at Marathon’s Keys Fisheries, a mid-island seafood market and marina on the Gulf.
At the other end of the new Seven Mile Bridge, spend a lazy few hours by the water at Bahia Honda State Park, where you’ll find some of the only true sandy beaches in the Keys. Many first-time visitors expect the islands to be ringed in ribbons of sand, but because the surrounding reef prevents sand build-up, most natural beaches in the Keys are small and often rocky.
When you reach Big Pine Key—less than ten miles beyond Bahia Honda—hang a right and wind your way back to No Name Pub for a late-afternoon conch fritter snack. The historic pub sits in the middle of a Key deer habitat, so keep an eye out for the miniature white-tailed deer native to these islands.
From there, you’re just under an hour to Key West. For classic Conch Republic charm, you can’t beat Marquesa Hotel, a collection of four cottages surrounding a tropical courtyard with two pools just blocks from the bustle of Duval Street. The boutique hotel recently purchased two adjacent homes, which are slated to open later this year following renovations. And if you decide to stay awhile—don’t rule out the possibility—the Marquesa also manages six long-term rentals a few blocks away. For a contemporary-cool vibe and waterfront views, try the chic Marker Hotel, which opened at the end of 2014.
Like a tranquilizer dart to the system, a cold beer in the country’s southernmost city will banish any lingering thoughts of to-do lists or unanswered emails. Captain Tony’s Saloon, a favorite of Ernest Hemingway’s back when it housed Sloppy Joe’s in the 1930s, and Schooner Wharf, the dockside watering hole that calls itself “the last little piece of Old Key West,” are within walking distance of both hotels. Or grab a beer and a bite at Half Shell Raw Bar on the harbor. It’s the only restaurant in Key West that operates its own fish market, so your mahi mahi, snapper, and shrimp are as fresh as they get. Come sunset, avoid the Mallory Square crowds and venture out to Fort Zachary Taylor State Park, which stays open each night for the show.