From a drive to Key West to driving the entire Florida Keys, the perfect road trip is all about the pit stops: especially for conch fritters, tarpon fishing, and stellar photo ops. Here’s what you shouldn’t miss.
The Florida Keys are laid-back, delightfully kitschy…and best seen from a convertible. So throw some T-shirts and shorts in a duffel bag, fill up the gas tank, and leave plenty of time for snorkeling, walking in the footsteps of Hemingway—and of course Key lime pie. You’re on island time now.
The perfect road trip through the Florida Keys is all about the pit stops: especially for conch fritters, tarpon fishing, and stellar photo ops. Here’s what you shouldn’t miss.
Mile markers 108–90
A slice of Key lime pie at Mrs. Mac’s Kitchen in Key Largo.
From Miami, you could hop right onto Route 1 for a straight shot through the Keys, all the way down to the southernmost island, Key West (without stopping, the drive will take about three and a half hours). But why take the short route? Instead, once you pass Homestead, Florida, hook onto Card Sound Road, the only other way into the Keys. It’s just as scenic but with less traffic (there is, however, a one-dollar, cash-only toll). It’s also the only way to get to Key Largo’s no-frills roadside seafood joint, Alabama Jack’s, a rite of passage for anyone making this drive. Outside, you’ll find a row of Harleys; inside, a rock ’n’ roll band covering Johnny Cash . . . and some of the most deliciously salty, meaty conch fritters you’ll ever find (58000 Card Sound Rd.; 305-248-8741; entrées from $11). Once you’ve had your fill, turn back onto Route 1, the Overseas Highway. About half an hour from Alabama Jack’s is Mrs. Mac’s Kitchen, which is worth a quick stop for a slice of the excellent Key lime pie (99336 Overseas Hwy.; 305-451-3722; entrées from $14). Finally, scuba enthusiasts won’t want to miss John Pennekamp Coral Reef State Park. It hosts up to 260 species of tropical fish and 80 types of coral (305-451-6322; scuba tours from $55 per person). Don’t want to get in the water? Do the glass-bottom boat tour instead.
Mile markers 90–63
The Albright House, a two-bedroom cottage at the Moorings Village.
The village of Islamorada actually comprises six tiny islands, so give yourself time to explore. It’s known as the sportfishing capital of the world, so it’s no wonder the seafood restaurants are as good as they are—in fact, they’re destinations in their own right. If you’ve come to fish, sign up for a four-hour trip aboard the Capt. Michael, which sets sail from Robbie’s Marina on the bay side of Islamorada—even amateurs will hook some tarpon in these teeming waters (305-664-8070; fishing trips from $40 per person). Diving is huge down here—to see just how huge, visit the History of Diving Museum. It contains an astounding number of marine artifacts, including bell helmets and armored diving suits, and is the largest collection of its kind in the world (305-664-9737). Beaches, on the other hand, aren’t the big draw in the Keys: The water tends to be shallow because of the coral reefs, and there’s not much wave action. Still, go to Anne’s Beach if you want to put your toes in the sand. It’s wonderfully secluded, and the water is crystal clear and warm year-round.
Eat like a local
We weren’t kidding about the seafood restaurants. They’re everywhere, and they’re perfectly laid-back. At Lazy Days Restaurant (see what we mean?), request a table on the beach and order the catch of the day—ask for it “Lazy style” and they’ll prepare it with panko bread crumbs, tomatoes, scallions, Parmesan cheese, and a dollop of Key lime butter (79867 Overseas Hwy.; 305-664-5256; entrées from $15). If you’re near Robbie’s Marina, grab a blackened grouper sandwich at the Hungry Tarpon, an old-school fish shack that’s exactly the kind of place you were hoping to find (77522 Overseas Hwy.; 305-664-0535; entrées from $13). Come dinnertime, you may be seeking something a little less fish shack–ish, so try Pierre’s Restaurant at the colonial-style Morada Bay (try to get there in time for sunset). It serves sublime seafood with an Asian twist, such as miso-honey marinated grouper and seared tuna tataki with Key lime ponzu sauce (81600 Overseas Hwy.; 305-664-3225; entrées from $32).
Where to stay
Islamorada is about halfway between Miami and Key West, so it’s a good place to spend a night or two. The gloriously secluded all-white boutique hotel Casa Morada (run by three hoteliers who cut their teeth working for Ian Schrager) was recently renovated and has 16 suites, along with numerous high- and low-adrenaline activities on offer, from scuba diving to yoga (305-664-0044; doubles from $399). The charming Moorings Village, a cluster of cottages set on a former coconut plantation, has a private white sand beach (for more of those throughout Florida, see page 88), a swimming pool, and orchids everywhere. Book one of the colorful cottages facing the beach (305-664-4708; doubles from $419).
Mile markers 63–47
a half-hour drive from Islamorada is the ten-mile-long island community of Marathon. Time your stop here around lunch, just so you can eat at the fifties-era diner the Wooden Spoon: Order the divine BLT (7007 Overseas Hwy.; 305-743-8383; entrées from $5). Once back on Route 1, drive a few minutes and you’ll come across a roadside stand selling 50-cent coconuts (down here they rely on the honor system—simply drop your coins in the cup). Grab a coconut and pull out your camera: This particular stretch of highway, Seven Mile Bridge, is made for photo ops. It’s just the road and the big blue for much of it. Also worth a stop is the tiny, made-for-picnicking island of Pigeon Key, nestled underneath Seven Mile Bridge on the edge of Marathon. In the early 1900s, the island was a base for 400 workers building the Key West extension of Henry Flagler’s Florida East Coast Railway.
Mile markers 4–0
Conch chowder and a BLT with fries at the Wooden Spoon in Marathon.
The southernmost town in the United States has always drawn the creative and kooky. Everyone from Jimmy Buffett to Tennessee Williams to Judy Blume has called it home, and it was even the site of President Truman’s Winter White House. Then there’s Hemingway, whose house is now a museum (he wrote The Snows of Kilimanjaro and To Have and Have Not when he lived there from 1931 to 1939). Ernest Hemingway Home contains all the furniture he and his wife Pauline had shipped here from Paris (305-294-1136).
Spend a few days wandering amid the gingerbread-style houses, free-roaming chickens, and art galleries of this hippie outpost, which feels a bit like a Caribbean New Orleans. The island isn’t known for its beaches—although the calm waters are great for snorkeling—but Smathers Beach, in the middle of the island, and Fort Zachary Taylor Beach, at the westernmost end, are good spots to throw down a beach towel.
Eat like a local
Pepe’s Café is the Keys’ oldest restaurant (it’s been around for 105 years) and the place for breakfast. The signature pan-fried mashed potato patty with scallions runs out fast, so go early (806 Caroline St.; 305-294-7192; entrées from $17). La Crêperie began as a food cart and is now, ten years later, an island fixture—the best seats are out on the porch (300 Petronia St.; 305-517-6799; entrées from $13). For lunch, head to Sandy’s Café, a hole-in-the-wall sandwich joint where the meat feast Cuban Mix is a must—it’s perfectly complemented by an iced café con leche (1026 White St.; 305-295-0159; entrées from $12). The (relatively) fancy option in Key West is Seven Fish, which serves sensational seafood dishes, like yellowtail snapper with yellow curry sauce, and grouper sushi with avocado and sesame, served warm (632 Olivia St.; 305-296-2777; entrées from $17). And at sunset, venture over to the Tower Bar at Turtle Kraals, which gets the vibe and the view just right: Grab a seat on the second-floor deck, order a Key West Sunset Ale, and drink them both in (231 Margaret St.).
Where to stay
In the past decade, the island has reestablished itself as a stand-alone getaway for those looking to bypass the rest of the Keys, so there are plenty of hotel options for all types of travelers (honeymooners, families, long-weekenders). One of the island’s oldest hotels, Casa Marina has lured business tycoons and dignitaries since it opened in 1920. Now a Waldorf Astoria property, it’s just as luxe but has grown to include 311 rooms, two beautiful pools, and Key West’s largest private beach. It’s also a short walk from Duval Street, a vibrant stretch known for its shopping and nightlife (305-296-3535; doubles from $349). The much smaller Marquesa Hotel is just as lovely and set in the heart of the historic district. Built in 1884 as a private home, it’s been beautifully restored and now has 27 rooms around a courtyard with two pools (305-292-1919; doubles from $395).