Travel on 2 wheels: Bike 100 miles in the Keys

Driving the 100-plus miles that link the Florida Keys’ limestone and coral islands ranks as one of America’s epic road trips.

I wanted to experience it on two wheels instead of four. The plan: Bike the country’s “southernmost century,” cycling-speak for a 100-mile journey in a single day, from Key Largo to Key West.

We all know that plans, especially in travel, often go awry. Last-minute logistical glitches meant my husband and I had to spread the ride over two days instead of one.

This snafu turned out to be a coup. It forced us to slow down and savor an experience that spanned the spectrum from goose-bump-inducing euphoria to hair-raising fear involving semi trucks, Seven Mile Bridge and the prospect of becoming shark chum after plummeting 65 feet into the Atlantic Ocean. This ride gave me all the feels. But let’s backpedal to where it began, at Key Largo Bike and Adventure Tours, owned by Islamorada resident Mark Terrill.

Terrill probably knows more than anyone about cycling in the Keys. The former cop compiled his expertise into a PDF he sells for $5 on It’s part cycling guide, part police blotter, full of vignettes about drug busts, murders and other ugly events that unfolded on these beautiful islands.

Terrill’s company offers a bunch of cycling trips, from century rides and beer-and-bike tours to customized itineraries. You could, for example, fly into Miami, hop on a bike and pedal your way to the mostly finished 106-mile Overseas Heritage Trail that ends in Key West, while your luggage gets shuttled from hotel to hotel.

On this balmy, breezy December day, Terrill was shepherding an 81-year-old Colorado man and his wife on a two-day trip from Mile Marker 100 in Key Largo all the way down to Mile Marker 0 in Key West. (Two-day guided trips cost $500 a person.)

My husband and I did the same thing, but on our own. We rented hybrid bikes and cycled roughly 50 miles to Marathon, where the Colorado couple spent the night and we caught a lift with Terrill back to our Key Largo hotel. The next morning, Terrill drove us to where we’d left off in Marathon, and we cycled the remaining 50 miles to what’s literally the end of the road: the southern terminus of U.S. Highway 1, which starts more than 2,300 miles away in Fort Kent, Maine.

The irony of cycling through the picturesque Keys is that much of the ride isn’t particularly scenic — until it is. Then it’s a showstopper. Biking over dozens of bridges delivered infinite vistas of tranquil water with more blue hues than a Sherwin-Williams warehouse. Palm trees swayed in the wind, and leggy herons stood guard in tangles of mangrove roots. But these highlights were interrupted by long stretches of strip malls and billboards flanking some of the more developed sections of the route. We often were within earshot of the roar of traffic on U.S. Highway 1. Sometimes you have no choice but to bike on the road’s shoulder, which might be as wide as 10 feet or as narrow as 3.

Even quieter segments of the trail pose hazards, like oblivious motorists pulling out of driveways and bright green iguanas playing “Frogger” on the bike path. But if you stay alert and are in reasonably good shape, the ride is doable. And it’s a ride worth doing, especially when you consider the route’s fascinating history.

A little more than a century ago, the only way to reach Key West was by boat. Millionaire Henry Flagler changed that with his wildly ambitious plan — initially dubbed Flagler’s Folly — to build an overseas railroad connecting the Keys to the mainland. The undertaking involved unprecedented feats of engineering, including the construction of a 7-mile bridge over open water.

Deemed the Eighth Wonder of the World when it debuted in 1912, the railroad was largely destroyed by the infamous Labor Day hurricane of 1935. The ferocious storm also killed hundreds of workers — many of them World War I veterans — who were in the Keys to work on the Overseas Highway, a predecessor of today’s asphalt lifeline between the Keys and the Florida peninsula.

Their cremated remains are part of a hurricane monument at Mile Marker 82 in Islamorada (where much of the Netflix series “Bloodline” is filmed), one of our first stops. It was the kind of short-but-worthwhile side trip we likely wouldn’t have made if we’d had to mow down 100 miles in a day.

If we’d stuck to our original plan to do a century ride, we also probably would have blown right by Robbie’s Marina, where you can feed massive tarpon by hand. We would have missed spotting endangered Key deer prance into the woods as we tacked on a few extra miles for a conch fritter lunch at No Name Pub, a dive bar on Big Pine Key. The inside of this onetime brothel is covered with dollar bills. “A quarter million,” said our waitress, who must wish she had a buck for every time customers asked, “How many?”

A more leisurely pace also meant we could poke around the beaches of Bahia Honda State Park and take a break at Mile Marker 40’s Veterans Memorial Park, where a rickety boat that carried 17 Cubans to U.S. shores in 2013 sits on display.

My favorite part of the ride was cruising along Long Key Viaduct, a parade of concrete arches that once serviced Flagler’s railroad and the old Overseas Highway. Cars have since been booted off to a new bridge built parallel to the viaduct, bequeathing this 2-plus-mile span to fishermen, joggers and cyclists. We rode alongside soaring pelicans searching for prey below, where the Atlantic meets the Gulf.

Terrill said most cyclists’ favorite part is going over Seven Mile Bridge. I was too busy catastrophizing scenarios of 18-wheelers sending me to a watery grave to enjoy the scenery.

The exhilaration of surviving those seven miles unscathed stayed with me all the way into Key West, where we casually pedaled along the Atlantic to the Southernmost Point monument, where Cuba — some 90 miles away — was closer than our Key Largo hotel.

Mile Marker 0 was just a short ride from there, followed by an even shorter ride to the Green Parrot Bar for a celebratory beer and rendezvous with Terrill.

We took our time — and plenty of photos — at these last few stops. After all, it’s the Keys. What’s the rush?

Reader Comments ...

Next Up in Travel

For a longtime powder-chaser, still some lessons to learn
For a longtime powder-chaser, still some lessons to learn

Snow whips at my group of six from all directions. Having just left the warmth of the waffle shack at the top of Jackson Hole Mountain Resort's tram, it feels especially cold and wet. Still, standing in our skis, arranged in a line at the top of Rendezvous Bowl, we all begin disrobing our upper halves. Each of us is wearing between three and five layers...
Beauty rises from a Virginia prison where suffragists changed history
Beauty rises from a Virginia prison where suffragists changed history

LORTON, Va. — The windows in Martin Cervantez’s towering artworks never look the same, their gentle colors changing subtly with the arc of the sun. They also never look like what they once were: tower windows from which guards watched inmates at the notorious Lorton Reformatory. Those windows are emblematic of the change from correction...
Brooklyn beckons with new hotels, other perks
Brooklyn beckons with new hotels, other perks

Jake Gyllenhaal is walking into my New York hotel. It’s not on Fifth Avenue or one of the trendy corners of Lower Manhattan. It’s in Brooklyn. And it — the 1 Hotel Brooklyn Bridge — might be the buzziest new hotel in the city, star sightings or no. Because the 1 Hotel Brooklyn Bridge, like the new William Vale Hotel and the...
Most air travelers say taking off your shoes is okay. An etiquette expert disagrees.

Unless you are ensconced in first class, sleeping on a plane is as intimate as dozing off in a waiting room on jury duty - everyone on the aircraft knows the decibel level of your snoring and the sad state of your socks.  To gauge how passengers perceive and handle nightmare flight scenarios, British Airways surveyed 1,500 travelers from the United...
When New York City was a (literal) battlefield
When New York City was a (literal) battlefield

NEW YORK — New York City is a battlefield. I know what you’re thinking — psychological warfare, the endless grim clashing of economic forces — but I am being literal. When we ponder America’s defining war, the Revolutionary War, we think of Bunker Hill, or Saratoga, or Lexington and Concord, yet its largest battle, a vast...
More Stories