From the outside looking in, our setup for this four-day trip was pretty simple. Two boats, five guys, 100 beverages, and a weeks’ worth of stoke and food. We had a crew of Brian Grubb, Parks Bonifay, Steel Lafferty, Bryan Soderlind, and myself, Jake Ramsdell. The plan was to drop two boats somewhere below Fort Myers on the west coast of Florida and then to trek across the state via the Okeechobee Canal. If you’re not from Florida and this sounds a little strange to you, well, it is. The Okeechobee Canal was created in 1937 to help control the flow in and out of Lake Okeechobee, the tenth largest freshwater lake in the country, and to give boats easier passage between the Gulf of Mexico and the Atlantic. The trip from coast to coast is 152 miles, with five locks you have to pass through. We had a rough estimate how we would do on gas, rations, and camping, but no clear idea on whether or not it would all actually work. Plus, you never know what the weather’s going to do. But as far as we knew, this would be the first trip like this with wakeboard boats, and all of us were down for an adventure.