As we dive into planning our cruise from St. Petersburg to Rock Hall, the first major decision lies before us: how to navigate from the west coast of Florida to the east coast. By car, one would simply drive from west to the east in a straight shot, rather than making an extensive circumnavigation south around the Florida peninsula and through the Keys. But alas, our boat is bound to water, not to wheels. So that direct line is not possible for us. Or is it?

Enter the 134 nautical miles (154 miles or 248 kilometers) long Okeechobee Waterway—an aquatic masterpiece that seems almost too good to be true. This engineering marvel, running from the Gulf of Mexico near Fort Myers, across Lake Okeechobee, and spilling out into the Atlantic near Stuart, promises the perfect shortcut for cruisers. No more rounding the southern tip of the state; instead, you can follow an almost straight shot through its middle, enjoying the serene beauty of Lake Okeechobee and the calm waters of the St. Lucie Canal.

The history of this waterway is as fascinating as the journey itself. Completed in 1937, the Okeechobee Waterway was envisioned as a commercial route to boost economic growth. Over the decades, it has evolved into a popular passage for recreational boaters and a crucial link in Florida’s nautical network. Each year, thousands of cruisers navigate this route, their vessels passing lush landscapes and quaint communities, enjoying the mix of nature and convenience.

Sounds too good to be true? Well, it is. At least for us. The Port Mayaca Railroad Lift Bridge, a seemingly innocent structure along the waterway, looms ahead with a clearance of a mere 49 feet when opened. And here we are with Koko’s mast, standing tall at 54 feet (plus some more for VHF antennas and such.) What a bummer! Our excitement about trying the Okeechobee Waterway dashed by those stubborn 5-7 feet.

And so, it is back to the drawing board for us. We will explore alternative routes and embrace the adventure of finding another path. Stay tuned.