Taking on the Everglades Challenge

Published on August 8th, 2021

A full weekend of windward-leeward races might be ideal for the advanced competitor, but far more sailors just seek a purpose to be on the water. But some purposes are more extreme than others as detailed in this report:


When David Hosler moved back to Florida after being in California for several years, he went looking for ways to rediscover the Florida he left behind years before. One day, an old friend came into his music store with the perfect solution, the Everglades Challenge.

This fateful day helped Hosler rediscover his passion for the sport of sailing and journey into his love of the unknown.

The Everglades Challenge is an unsupported, expedition style race for small sailboats, kayaks, and canoes. Competitors have eight days to travel the roughly 300-mile distance without any assistance from safety boats or support crews. The Challenge course follows the Florida coastline from Fort Desoto to Key Largo, with much of the race occurring within the boundaries of the Everglades National Forest.

Intrigued by the idea of participating, Hosler began looking into the Challenge. “I had just picked up sailing again; I sailed when I was younger, but it had been a while since I had been out in a boat. So that first year I just went out and watched the boats launch,” he says.

After seeing the boats launch, he was hooked and knew he wanted to be a part of it as a competitor. The first challenge was figuring out what boat to use. He spent the next year building a Chesapeake Light Craft (CLC) Dory with his grandkids. The boat was compact but had sufficient storage for the expedition style voyage.

Looking back, Hosler chuckles remembering his first time participating in the Challenge. “I didn’t really understand the challenging nature of it and I way overpacked,” he says. “I treated it as more of a camping trip than a sailing challenge. I would stop and pitch a tent and build a fire, I didn’t realize that you had to keep moving.”

For the first year Hosler had his grandson with him, and the pair made it down to the end of Tampa Bay before treacherous weather forced them to end their journey. Hosler was not deterred, though the following year saw bad weather once again sidelined his efforts.

“I went solo that second year, I ultimately crashed onto a beach and a sandbar caught the boat and flipped it over,” Hosler says. “After that, my wife told me that I could never do the Challenge in the CLC Dory again.” Enter: The RS Venture. “The Venture has been the best boat imaginable,” he says. “It is a really nice, stable sailing boat. If you want to go fast you can, but you don’t have to. Plus, it’s wide enough that you can sleep in it.

“I sailed the boat at night for two nights and never had any concerns. We got caught in one big storm and we just anchored the boat and hung on, but the boat did really well in those conditions, and we were never concerned for safety.”

Hosler’s third attempt saw him go the furthest he has ever gone “I made it all the way to the third checkpoint,” he says. “Unfortunately, the breeze was coming straight out of the east, which has a tendency to drain the water out; so we ended up at the wrong key, 30 miles south of the finish line.”

But for Hosler, the event is not about winning or losing. “I’m honestly not a racing sailor,” he says. “I am much more of a leisure sailor, but I love the challenge.”

This year, however, the challenge was even more unexpected, and one faced by more than the sailors. With COVID-19 affecting races and events across the world, there was uncertainty about whether the Everglades Challenge would happen this year.

But, after working with local health officials, it was decided that given the nature of the event it did not pose a large health risk and was allowed to proceed. This year, Hosler made it to the second checkpoint before bad weather and strong winds forced him to retire. But, regardless of results, Hosler plans to continue competing in the Challenge.

“I have loved getting involved in the Everglades Challenge,” he says. “The expedition style racing definitely makes it a challenge and different than anything I’ve done before. It is a huge motivator for me to stay fit and I love the camaraderie between all the racers; I will probably do it until the day I die.”

Source: RS Sailing

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