in the Florida Keys is especially fun on stretches
where you don't have to worry about riding next to
LARGO, Fla. — Driving the 100-plus miles that link the
Florida Keys’ limestone and coral islands ranks as one
of America’s epic road trips.
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.
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.
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
probably knows more than anyone about cycling in the Keys.
The former cop compiled his expertise into a PDF he sells
for $5 on www.keylargobike.com. It’s part cycling guide,
part police blotter, full of vignettes about drug busts,
murders and other ugly events that unfolded on these
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.
I moved here 20 years ago, hardly anyone biked for
fun," Terrill said. "As the trail gets developed
and they build wider shoulders on the road, more cyclists
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
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. (We saw at least 100
cyclists with an organization called Pedal Across
Wisconsin doing a similar ride on a five-night, round-trip
journey between Key Largo and Key West;
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
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.
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.
building of ‘the railroad across the ocean’ was a
colossal piece of work, born of the same impulse that made
individuals believe that pyramids could be raised,
cathedrals erected, and continents tamed," writes Les
Standiford in his 2002 best-seller, "Last Train to
Paradise," a must-read for anyone traveling the Keys.
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.
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.
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?"
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
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.
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
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.
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.
took our time — and plenty of photos — at these last
few stops. After all, it’s the Keys. What’s the rush?