Flagler’s Folly


By James Favors

While heading down to the Florida Keys this winter Lisa and I had two options. We could either cruise from Fort Myers Beach on our boat, or trailer Kismet from the west coast of Florida driving across, then south down the Keys, all the way to Key West. Ultimately we chose the latter. We wanted to have our own transportation available to us once we reached Key West Harbour Marina on Stock Island where we had booked a month’s dockage. Our desire was to relax, and soak up the sun and eclectic lifestyle of the most southern, tropical local in the United States. After our short side trip to the Everglades we continued our journey east, via Tamiami Trail then south through Homestead on Route 1. As we eased our way through Homestead and finally into the entrance to the Keys on Route 1, I couldn’t help but contemplate how getting through the string of islands that make up the keys was made so much easier by “Flagler’s Folly.”

Here I am, at Goodland’s Calusa Island Marina, making my walk around inspection before heading out onto Tamiami Trail.

For those that don’t know about Henry Flagler, he was an industrialist and one of the founding partners of Standard Oil Company along with John D. and William Rockefeller in 1870. Henry Flagler made a fortune from his time with Standard Oil and eventually progressed to new ventures in eastern Florida. The actual “Folly” started in St. Augustine, in 1885 when he made plans to build the Ponce de Leon Hotel. Knowing he would need to have a reliable way for people to get to his new hotel (remember this was 1885) he formed the Florida East Coast Railway. The short story, from here out, is that he kept extending the train line south, built more hotels in towns along the way, including the historic, 1,100-room, Breakers Hotel in what is now Palm Beach.

After Henry’s railroad made it to the outpost of what is Miami today (he’s considered the “Father of Miami”), he formed the Overseas Railroad in 1905. His objective was to connect 128 miles of individual Florida Keys, all the way down to Key West, with his Overseas Railroad. Completed in 1912, the line provided the first means of transportation through the Keys other than by boat or plane. Long after Mr. Flagler died, because the railroad was so badly destroyed by the 1935 “Labor Day Hurricane,” the company simply could not continue financially. This is when the State of Florida bought the railroad and built the Overseas Highway using some of the remaining infrastructure. It’s because of Henry Flagler’s vision, to connect this string of tropical islands by railroad, that we have the option today of being able to trailer our boat the 128 miles to the southern-most point in the United States, Key West.

Yes, they’re that close, it’s a good thing there was a fence between the gators and us.

About the time my Henry Flagler daydream came to an end, we were crossing Jewfish Creek, the body of water that separates mainland Florida from the Keys. The section of Route 1 from Homestead, across Jewfish Creek and into Key Largo was the same route Henry Flagler used when he started the seven-year quest to bring his railroad to Key West, over a hundred years ago.

Remnants of the Overseas Railroad are still standing at the beginning and end of many of the keys, a living, although somewhat decaying, testament to a true visionary. The remains are now either abandoned or converted into walking and/or fishing piers out over the tropical waters separating Florida Bay from Hawk Channel and the Atlantic Ocean. Most of Route 1, in the Keys today, rests where the old railroad bed was and consists of mostly two lanes, sometimes four, but all certainly modern enough to handle towing our Ranger Tug safely to our first stop, this season, Marathon.

Here you see, from the Keys side, the relatively new Jewfish Creek Bridge that we crossed to reach the Keys.

I'm not sure if it’s me, or how we personally go about trailering our boat from one location to another, but it seems to be an all day affair. I'm talking about the days where you start by having to take your boat out of the water. In this case we were anchored out by Goodland, Florida, so our trailering day started there and ended in Marathon, Florida, a distance of 178 miles. To review our process, we started our day by waking up at 7 a.m., showering, and eating before we took the boat to the ramp around 9 a.m. It took an hour to retrieve the truck and trailer, then load and secure the boat – we were finally on our way by 10 a.m.

After a couple of hours traveling east on Tamiami Trail our stomachs started growling, letting us know it was time for lunch. We waited until we arrived in the metropolis of Homestead to look for a place to stop, as restaurants are quite limited on this stretch of road. When it’s all said and done, you can count on a stomach refueling to add about an hour to a day’s travel. Back on the road, we intersected Route 1 and made it to Marathon around 3:30 p.m., but we still weren’t really there yet, just at the ramp. We still had to launch the boat, cruise a short distance to the marina, tie up the boat; register and then we had to walk back to the ramp, about a mile, to retrieve the truck and trailer. By the time we were able to sit back to relax with a glass of wine and join our new neighbors to watch the sunset over Florida Bay we had invested a total of 10 hours. It took 2 hours getting ready and prepping to get to the ramp in the morning. Then it took 1-hour to load in Goodland, 3.5 hours driving to Marathon, an hour stopping to watch and photograph the alligators in a drainage ditch in front of the Visitors Center only feet from Tamiami Trail, 1 for lunch, 1.5 hours unloading, getting to the marina, retrieving and securing truck and trailer.

This Seven Mile Bridge sign, in Marathon, lets walkers and bikers know that this span was a railway bridge until 1935.

By chronicling “a day in the life of trailer cruising” I want our readers to understand that without the ability to trailer our boat this way the alternative trip, by water, would have taken two to three days. Because we've experienced this route before by water, we didn't feel we were missing out on anything new, so instead of the two or three-day trip, we were able get to the same place in one 10-hour day. The additional upside in this scenario is that we didn't have to worry about a potential bad weather delay and we had our own land transportation upon arrival. Even though 10 hours was a long day, once we were settled in, we were ready for a weeks stay in Marathon, a stay lengthened by being able to trailer our boat to the destination. It was time to let the Keys' slow-paced way of life seep into our existence. We were ready.

Wikipedia defines a key as “a small, low elevation, sandy island formed on the surface of a coral reef.” Marathon is located mid-way into the Keys and is made up of eight islands, Vaca Key being the one we were heading to. We've been to Marathon before, even to the Harbour Cay Club were we reserved a weeklong stay, but it was always as a one or two-day stopover. We were looking forward to staying a full week in Marathon to visit with friends, (mostly other boaters in the area), watch sunsets, eat fresh seafood, and above all, relax.

Just past the arrow sign you’ll see the remnants of a small, two-lane road that the railway bridge was converted to in 1935.

In 1982 a new Seven Mile Bridge, seen to the left in this photo, replaced Henry Flagler’s Seven Mile Railway Bridge.

When I say “relax,” I'm talking about the kind of mindset where you wear shorts every day, sometimes the same pair for days on end, even when they have stains. Sandals are a given, which means there is no place or time you'd be wearing socks. It's time to let the phones go to message, plan the day’s eats and drinks for happy hour and your most serious debate typically revolves around either the quality of sunset or who has the best lunch or dinner special. It seems to be an infectious virus, one where you lose track of what day it is or when you have to think long and hard about what the exact date is. It's time to leave normal civilization and all its trappings checked back at the mainland side of Jewfish Creek. It’s time to chill out and let the days unfold as they did when we were all children enjoying a long summer’s day, with no cares in the world, it’s time to willingly subject yourself to a well known phenomenon, “Keys Disease.”

Wade and Susie, long time boating friends, sitting under the “Cone of Knowledge” with me, getting ready to swap stories and watch the sunset.

Shortly after our arrival, and a little before our first Marathon sunset, we were invited to join the boaters residing at Harbour Cay Club’s “Cone of Knowledge” (Tiki Hut). We heard this is the place they like to swap stories, have an adult beverage and watch the sunset, but above all else, we think they were purposely gathered there to help spread that virus to a couple of healthy boaters from the north who had just arrived. Thanks Henry!