Cycling the Florida Keys Overseas Heritage Trail

By: Herb Hiller

The “Tour to Land’s End” isn’t yet complete. But even a partial passage is more than worthwhile.

Today completed sections of the Florida Keys Overseas Heritage Trail chiefly attract locals with shopping baskets on fat-tire bikes they pedal to nearby food markets and laundromats. But by mid-decade when the trail may be 95 percent paved and off-road it will roll out the biggest getting-around improvement for visitors to the Florida Keys since road replaced rail after the Labor Day Hurricane of 1935.

A man rides his bike along the Florida Keys Overseas Heritage Trail in Marathon Key.

Photo: Patrick Farrell for VISIT FLORIDA

The 106-mile trail will link Key Largo with Key West across 37 bridges many off-limits to cars and where the rarely absent tailwind wraps around bare arms and legs just as it churns blue water below.

I had my own wild moment during the four days when a friend named Ted and I recently cycled along part of the route. We crossed the Seven Mile Bridge on the paved shoulder exposed to crosswinds. We hugged the low barrier away from cars where I imagined a wind gust blowing us bikes and backpacks to the bottom. I walked the bike up the hump of the bridge that allows high-masted boats to pass beneath. On the way down I flew. The wind blew. I squeezed my brakes.

Everywhere beauty and caution contrast the ride. Strong cyclists can handle it in two days paved and unpaved sections alike riding the often narrow shoulders. Count on at least three days for the rest of us.

The route varies. Long in-place sections carry you through Key Largo Islamorada and Marathon – 47 miles on these sections alone. But there’s trail and there’s trail. Toward Tavernier where trees supply shade roots buckle the pavement.

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

You grasp how the entirely finished trail will favor the continuing comeback of bikes from when cycling was fresh and so were the bridges built by an aged Henry Flagler for his “Railroad that Went to Sea.”

Now the compulsion that drove Flagler drives cyclists.

From a car the road through built-up areas is often crowded often just two lanes filled with motorists itchy to get around local traffic. You stop for a restaurant maybe a motel overnight a sandals outlet or crafts shop.

The old 7-mile bridge, alongside the newer bridge, is a beautiful stretch of the Florida Keys Overseas Heritage Trail.

Photo: Patrick Farrell for VISIT FLORIDA

Although today’s mile markers are made of green metal people in cars passing a thrift store on Big Pine Key likely won’t see the last remaining mile marker still in its low place from railroad days a relic stone that reads “492 JAX” on one side “30 KW” on the other. Look for it as you pedal by.

Likely also missed at the ranger station of Long Key State Park is a rusted section of track used by trollies that carried luggage from the rail line to the site of the Long Key Fish Camp. Western writer Zane Grey fished here with Flagler’s pampered swells. That was a fab Florida getaway.

Driving you won’t miss the bizarre logo eye at Baby’s Coffee on Saddlebunch Keys but chance might deny you a close-up of a great white egret with yellow beak and eyes painted mascara blue-green. And you will miss the chain-link bike parking rack that seems to defy gravity along the Grassy Key Trail where a dirt path slips to the bay.

In cars you stop for gas. On bike you stop anywhere to avoid saddle soreness.

One lucky stop was at an Islamorada parking lot backed by a billboard-sized mural of the first train crossing the Long Key Viaduct. On a blowy night car lamps illuminate Flagler's sophisticates at their dressy leisure. Outside a beam searches the way forward and the steamy hiss of brakes prepares a stop over stormy waters. Flagler himself with a Mona Lisa smile shines down as the man in the moon.

At the end of a cycling day Ted and I avoided riding or walking to dinner in the dark. We ate early one evening at a waterfront place in Tavernier. We arrived early enough to score $28 fresh fish dinners and two-for-one beer and wine. A guitarist under a boat top covered Buffett songs. At the deck bar tourists were getting high. Paradise.

I didn’t feel it. Expedition mode possessed me. We had packed next to nothing. We washed clothes every night. Once after 45 miles I slept for 12 hours. You do wonder what’s the point of four days for what you can otherwise drive in a scant three hours. Yes the exploration but even four days isn’t long enough fancies Department of Environmental Protection Trail Specialist Monica Woll.

Woll calls four days “ridiculously fast. Slow down. Take two weeks.  Get to the beach.” (Although beaches are few.) She recommends a walk to the Flagler-era work camp on Pigeon Key that’s at the end of a two-mile lopped-off bridge (no cars allowed). She prefers calm days when you can see sharks manta rays and turtles in clear water below. I’ll add to Pigeon Key the mile and a half ride west out of Big Pine Key to the No Name Pub that opened a year after the killer hurricane of ’35 -- woody funky and dim as ever dollar bills pasted all around like wingy stingy things on fly paper.

Fisherman go about their business as the sun sets off Marathon along the Florida Keys Overseas.

Photo: Patrick Farrell for VISIT FLORIDA

You enter Key West exultant along the trail through the hugger-mugger of New Town. I prefer this option to riding the mile-longer beachside trail precisely for its urban clash after the last stretch of boring shoulder. Here instead one finds the din of supermarkets pizza joints jet ski rentals chain hotels. “Pity the drudges ” I say to myself imagining my arms thrust high in a triumphant breasting of the Tour de France finish line. Yes me who won’t dare take his hands off the bars for anything!

You’re pumped for Old Town -- Toon Town -- beyond the reach of fast cars. Instead cars so slow that on a narrow clogged street a cyclist wearing a parrot on his shoulder calls to a motorist “Get a bike!” We lock ours ready to party.

NOTE: The ride down is unequaled. The ride back is either all the way into the wind or by Greyhound that requires you to box the bikes; two to Miami International Airport for about $230. You can rent a minivan for about $150 including gas. Easy choice.

For information about the Florida Keys Overseas Heritage Trail including maps see

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bicycling in the keys Heritage Trail here i come but firat california
There are plenty of places to visit and see in Florida Keys. If you haven't been there, you should ). Sunny Isles Beach Florida Real Estate .
If you live in Sunny Isles Beach Florida you can go to the city pier and quite often see them swimming.
I've written up my personal account of Cycling Florida Keys from Key Largo to Key West . This is a lot harder than it sounds in 2 days!

Nice article. There is another option to finish this ride by taking the ferry to Fort Myers.

My husband and I are planning our third bicycle trip loop to Key West and back. We begin in Fort Myers and ride to Key West, finishing the trip by hopping on the ferry from Key West, which takes us back to Fort Myers. It is a fantastic trip. No need to ride back up the keys into the wind.
Can you give me the latest up-date on the Overseas Heritage Trail having plans to cycle late fall.
Thank You.