Tips for Biking the Overseas Heritage Trail in the Florida Keys

Locals with shopping baskets on fat-tire bikes pedal to adjacent food markets and laundromats on the completed sections of the Florida Keys Overseas Heritage Trail. However, by the middle of the decade, when the trail may be 95 percent paved and off-road, it will provide the most significant transportation upgrade for tourists pedaling the Florida Keys since road replaced rail following the 1935 Labor Day Hurricane.

The 106-mile track will connect Key Largo and Key West over 37 bridges, many of which are off-limits to cars, and where the tailwind wraps around naked arms and legs as it churns the azure sea below.

During the four days, I had my wild moment while cycling along part of the trip with a guy named Ted. We took the asphalt shoulder of the Seven Mile Bridge, which was exposed to crosswinds. I pictured a wind gust sweeping us, our bikes, and backpacks to the bottom as we hugged the low barrier away from motorists. I rode my bike up the hump of the bridge, which permits high-masted ships to pass beneath it. I flew on the way down. The wind was blowing, and I slammed on the brakes.

The ride is full of contrasts between beauty and caution. Strong cyclists can complete it in two days, riding the often thin shoulders on paved and unpaved sections. For the rest of us, expect at least three days.

Biking in the Florida Keys takes you on various routes, and long in-place parts take you through Key Largo, Islamorada, and Marathon, totaling 47 miles. There is, however, a difference between a trail and a trail. Roots buckle the pavement as you get closer to Tavernier, where trees provide shade.

A canopied three-mile neighborhood road through Islamorada that joggers and walkers also use; and a five-mile ride starting at the retrofitted historic rail bridge across Tom’s Harbor Cut that mostly avoids sight and sound of the highway, channeled by a screen of roadside buttonwoods and mangroves to the bay.

You can see how the fully completed route would encourage the continued revival of cycling, just as the bridges built by an elderly Henry Flagler for his “Railroad that Went to Sea” did.

The same urge that propelled Flagler now drives bikers.

The road through densely populated areas is frequently congested from a car, with only two lanes typically full with motorists eager to avoid local traffic. You make a pit stop at a restaurant, a motel for the night, a sandals outlet, or a crafts store.

Even though today’s mile markers are made of green metal, motorists passing a thrift store on Big Pine Key are unlikely to see the final remaining mile marker, a relic stone that reads “492 JAX” on one side “30 KW” on the other. As you pass past, keep an eye out for it.

A corroded stretch of track used by trollies to transport luggage from the train line to the Long Key Fish Campsite is likely also missing from the Long Key State Park ranger station. With Flagler’s pampered swells, Western writer Zane Grey fished. That was a fantastic Florida vacation.

If you’re driving, you won’t miss the odd logo eye at Baby’s Coffee on Saddlebunch Keys, but you could miss a close-up of a great white egret with a yellow beak and blue-green mascara eyes. Along the Grassy Key Trail, where a dirt trail drops to the bay, you’ll miss the chain-link bike parking rack that appears to defy gravity.

When driving a car, you have to stop for gas, and you can control anywhere on a bike to avoid saddle soreness.

The first train crossing the Long Key Viaduct was depicted in a billboard-sized mural in an Islamorada parking lot. Car lamps illumine Flagler’s sophisticates at their formal leisure on a windy night. Outside, a flashlight looks for a path forward, and the steaming hiss of brakes prepares for a stop above raging waters. Flagler himself shines down with a Mona Lisa smile as the guy on the moon.

Ted and I avoided riding or walking to supper in the dark after a day of biking in the Florida Keys. We had dinner at a beachfront restaurant in Tavernier early one evening. We arrived early enough to get two-for-one beer and wine and $28 fresh fish dinners. A guitarist covered Buffett’s songs under a boat top. Tourists from the bar were getting high on the deck. Paradise.

It didn’t feel right to me. The expedition mode possessed me. We had brought very little with us. Every night, we washed our clothes. I once slept for 12 hours after traveling 45 kilometers. What’s the sense of spending four days on something that could be done in three hours? Yes, the exploration, but even four days isn’t long enough, according to Monica Woll, a trail specialist with the Department of Environmental Protection.

“Ridiculously fast,” Woll says of four days. Take it easy. Allow two weeks. Get to the beach as soon as possible.” (Although there aren’t many beaches in the Florida Keys.) A stroll to the Flagler-era work camp on Pigeon Key, which is at the end of a two-mile lopped-off bridge, is recommended by her (no cars allowed). She enjoys quiet days when sharks, manta rays, and turtles may be seen in the pristine water below. I’ll add a mile and a half west of Big Pine Key to the No Name Pub, which opened a year after the devastating hurricane of 1935 and is still as woody, stinky, and gloomy as ever, with dollar bills plastered all around like wingy, stingy things on flypaper.

You enter Key West exultantly down the route, passing through New Town’s hugger-mugger. This option is preferable to the mile-long coastal trail because of the metropolitan contrast after the last stretch of the uninteresting shoulder. Instead, there’s a cacophony of supermarkets, pizza parlors, jet ski rentals, and commercial hotels. “Pity the drudges,” I think to myself as I see myself triumphantly breasting the Tour de France finish line. Yes, it’s me, the man who won’t take his hands off the handlebars for anything!

You’re excited to visit Old Town, Toon Town, which is beyond of reach of fast autos. Instead, cars move so slowly that a biker sporting a parrot on his shoulder yells to a motorist, “Get a bike!” on a tiny, congested street. We lock ours and get set to have a good time.