Driving Discovery: Cruise Through The Florida Keys

The 161-mile drive from Miami to Key West on US 1 can take you three hours, but if relaxing under towering palms, adventuring along endless beaches, and throwing back meals like Thai seared tuna sounds appealing, turn those three hours into 3 days of uninterrupted bliss. The scenic route crosses 42 bridges as it island-hops its way to the southernmost tip of the country. Here’s how you can get started.

Day 1: Miami to Islamorada

Just south of Miami, take I-95 South until it spits you onto US 1—the low-speed highway you’ll all the way to Key West. Along the way, take a detour to the Homestead-Miami Speedway where The Richard Petty Driving experience will take you for a racecar ride-along on the 1.5-mile oval. Or, try your own skills behind the wheel.

South of town the highway enters Everglades National Park before it officially leaves the mainland for the Keys. The Overseas Highway, as US 1 is called from here, is 127 miles long, and was largely built on a former railway route built-in 1912 by Henry Flagler, the railroad magnate who founded the city of Palm Beach. Much of the line was damaged by a hurricane in late 1935 and was reconstructed a few years later as an auto road.

After leaving the mainland, the route follows a thread of sand that splits Blackwater and Barnes Sounds before turning onto Key Largo. But instead of following the sharp right that US 1 takes south, make a left and drive north nine miles to snorkel among the sea turtles and tropical fish in the shallow reefs of Biscayne National Park. The Biscayne National Underwater Park dive shop at Convoy Point offers tours. Towel off and drive south for a dinner of Thai Seared Tuna and celebrity spotting by the water at Snapper’s Waterfront Restaurant and Tiki Bar in Key Largo. As the sun sets over the Everglades, drive south until you reach Islamorada, an incorporated village that spans six islands and remains protected by a barrier reef.

Day 2: Islamorada to Big Pine Key

Islamorada is Poseidon’s gift to sport fishing in the U.S., so rise before dawn, grab your fishing pole, and join a half-day trip on a fishing charter to stalk redfish, tarpon, and permit (yes, that’s a fish). At lunch, swap fish tales with the dining room full of regulars over conch fritters at Mangrove Mike’s Café, and then continue the journey to Marathon on Knight’s Key. Four ferries per day offer rides from Islamorada to Pigeon Key, a spit of land that once housed the headquarters for building the Overseas Railway. The tour of the structures and historical sites will make your drive from Knight’s Key onto the seemingly never-ending Seven Mile Bridge more meaningful. The current structure was completed in 1982, replacing the bleached bones of Henry Flagler’s original.

An evening’s rest awaits you past Big Pine Key near the Great White Heron National Refuge at Sugarloaf Lodge. It’s a mere 15 miles from your ultimate destination, but the thatched roof Tiki bar and private beach are worth the stopover.

Day 3: Big Pine Key to Key West

Make the short jump to four-mile-long Key West, and don’t stop until you hit the end of U.S. 1—quite literally the end of the road—on Whitehead Street. You’ll find Mile Marker 0 there, but good luck finding a parking spot. Once you do, make the required stops to places like the Hemingway House where the legendary author Ernest Hemingway wrote: “For Whom the Bell Tolls” and other novels. Before following in Hemingway’s boozy footsteps from Captain Tony’s—as so many locals and Key West natives love to do—take a stroll through the Key West Botanical Garden and Tropical Forest where more than 20 different butterfly species inhabit. The must-have, but not well known, lunch is a Cuban Mix sandwich from 5 Brothers Grocery and Sandwich Shop. From there, make your way to Mallory Square to browse the historical exhibits and then take part in the daily beautiful sunset celebration that begins while the sun still hangs high in the sky. When the daylight eventually does extinguish into the western sky, you can say you’ve reached the end of the road.