There’s nothing quite like taking a road to the end of the world. When that path takes you through a history of landscapes ripe with the romanticism of escape into the exotic, it’s all the better.
We’re talking about the Florida Keys. With rich, sultry names dotting the route—such as Key Largo, Islamorada, Theater of the Sea, and Key West—this string of islands speaks to sun-loving adventurers.
The area is famously lorded over by the spiritual presence of one Ernest Hemingway, who called Key West home. As a motorcycle destination, the Florida Keys present a unique, colorful, and highly memorable riding experience.
Navigation in new, unfamiliar places can sometimes be the bane of travel. The Keys are easy—there’s only one road.
Head south out of Miami and pick up US 1. Then it’s 98 miles of smoothly paved white road which will take you over 42 bridges (including the famous Seven-mile bridge, Florida’s longest) and across the 44 islands that make up the Keys, terminating at Key West, the southernmost point in the continental U.S.
Traversing this modern marvel of engineering, the slightly elevated highway takes you out over the water, far into the southern reaches of this line of islands, at times suspending you and your bike above the water with seemingly nothing around you. You’ll appreciate the unobstructed view from the seat of a motorcycle, placing you in an open-air spectator seat to the stunning scenery.
Need it be said? Top off your fuel tank before starting the trek.
Ride until you reach the end of the road, literally. US 1 South ends at Key West, the famous subtropical paradise sitting just 18 feet above sea level, rich with a colorful tapestry of quaint streets and charming homes, casual bars, good restaurants and essential tourist sites, such as the Hemingway House & Museum.
Writers, artists, and dropouts from society (in the best definition) have long been attracted to the warm weather, which brings a welcome atmosphere of laziness to the area. Just four square miles, Key West may be part of the U.S. but is a completely different world. A tourist haven, its remoteness tends to attract a different kind of traveler.
Once parked at the end of the road, you can stroll sandy beaches, go snorkeling, or take part in any number of water activities. Visit the many bars, windows open to the warmth, or enjoy a meal in a region famous for its seafood.
The Keys are a place where you don’t need to worry about being judged. You could wait in the long line to have your picture taken at the buoy marking America’s southernmost point (just 90 nautical miles from Cuba) and hit plenty of shops filled with knickknacks and the usual tacky tourist stuff.
Or, do what Florida and the Keys are famous for—relax in the warmth. Beachcombing and finding shaded spots to stretch out are a popular pastime here.
Facts & Information
Aside from the main road skirting the Keys, US 1, there are no alternate roads once you leave the mainland and head out over the water. That said, the route delivers unprecedented, 360-degree views from the seat of a motorcycle, with the clear turquoise water of the Keys keeping you company on all sides for the entire ride. At the end of the line, take the loop ride around this tiny southernmost town.
Recommended Lodging: Kimpton Winslow’s Bungalows
For a special overnight stay at this far south point, consider Kimpton Winslow’s Bungalows. Proudly boasting itself a “lush garden retreat with playful amenities,” the hotel is located roughly half a mile from the famous southern buoy. Situated amidst walking distance of the lively streets of old town, the Winslow Bungalows means being able to have a drink over dinner and not having to worry about impaired riding.
Also, there’s Banana Bay Resort. The name alone begs discovery. Relaxation is the theme here. Wake up to views of the Gulf Coast, lounge at the pool, or walk the sandy beaches.
Best Time to Travel
Famous for its four seasons of warmth, the Keys do also get their share of powerful storms and plenty of wet weather. It’s all part of the mystique. Keep a keen eye on weather, which can change rapidly—such is the character and nature of the Atlantic, especially in this subtropical zone. Hurricane season in the Caribbean, of which Key West is part of, runs from June to November. Afternoon showers are common. Temperatures vary from 65 to 89 degrees, rarely below 56 or over 91.