Everglades Challenge 2027

by Sean | Jun 14, 2026 | Expeditions, Personal, Races

It has been far too long (12 years) since I’ve done any sort of expedition or ultra-distance race, but now the kids are older and more independent, I have a bit more time and freedom to plan, train for, and execute an ultra and I have registered for the Everglades Challenge in March, 2027.

The WaterTribe Everglades Challenge officially began in 2001. Founded by Steve "Chief" Isaacs, this unsupported expedition-style adventure race for small craft, kayaks, and canoes is roughly 300 nautical miles (345 miles) depending on your course selection and follows the SW Florida coast line from Fort De Soto on the north side of Tampa Bay to Key Largo. After crossing Tampa Bay, you can follow the Intercoastal Waterway or paddle on the Gulf to the first checkpoint at Cape Haze at approximately 60 miles.

From Cape Haze you can choose to continue on the Intercoastal Waterway or head back out onto the Gulf on your way past Fort Myers to the second checkpoint near Everglades City, which is past the halfway point with roughly 160 miles completed.

You are then entering the Everglades National Park and are faced with another dilemma: To stay on the open coast and paddle 66 miles around Cape Sable or ‘cut the corner’ through the maze of mangroves, freshwater swamp and canals to Flamingo and the third checkpoint. The latter route also requires a portage back to the ocean once you eventually get to Flamingo. Not just because of the abundance of alligators my preferred route is to stay on the more familiar (to me) salt water but bad weather may force me to choose the fresh water route instead.

At first glance it looks like a relatively easy 30 plus mile island hop from Flamingo across Florida Bay to the finish on Key Largo. But here you have no real choice but to navigate through the maze of mangrove islands and shallows, and do your best to avoid running out of water entirely. Thankfully the tidal range is less than a foot but the actual depth of water covering the mud (yes mud, not sand) can be heavily influenced by the wind.

The weather in March in South Florida is unpredictable. It can be lovely, warm, even hot. But it can also be stormy and surprisingly cool. Like any open water paddling event, the wind will be the biggest factor and that is why many paddlers choose to carry a sailing rig. At this point in time I am not planning to use a sailing rig but will keep that option open as I work on my paddling endurance.

My friend Robby has offered to let me use his Stellar 18R G2 fast expedition sea kayak which is incredibly generous of him. I will be looking at other options too since I’m certain this race will take its toll on any kayak. I will do the majority of my training on my surfski but will need to get in a bunch of long days and overnights to dial in the kayak, my systems, my body and my mind.

As you can probably tell, I’m really excited about this challenge and I’ll try to share what I learn along the way.