Kayaking the Calusa Blueway in Florida
Story and photos by Tim Leffel

While tens of thousands of motorboats ply the Gulf Coast of Florida waters each day, skimming the water at a slower pace reveals a lot more details along the shores.

Great Calusa Blueway Florida wildlife

It’s like a highway, but one where there’s no traffic, one where the speed is purposely limited by the users, and where the scenery is more important than the destination. If you tried to stand on this highway, you would sink.

This route is not a riddle, but rather the Great Calusa Blueway in the Gulf of Mexico, off the western coast of Florida. For those who want to travel it, the vehicle of choice is a kayak, or lately a paddleboard. Most of the creatures residing at the exits are not human, but have wings or fins instead.

Great Calusa Blueway kayaking trail that travels along Pine Island, Sanibel, Captiva Island, and Fort Myers in Florida

I’ve long envisioned a trip of kayaking from island to island along the Great Calusa Blueway, a 190-mile signposted network of “trails” that go along the mainland and out to a series of islands big and small where calm waves lap the shore and no sea kayak rudder is necessary. The ambitious Blueway is a set of marked and mapped kayak trails that extends over the entire region. It goes from mangroves to unpopulated marine reserves and hidden beaches. It would take even the most experienced paddler a couple weeks to do the whole route.

I had fantasies of carrying basic camping gear and minimal clothing. I would swim in the sea and carry dehydrated food, moving along for miles and miles with just the power of my arms and a paddle. I would pull up to remote restaurants on stilts to get a hot meal sometimes, then paddle off again until the sun started sinking low.

My wife was having none of that though.

For the sake of marital harmony, we’re paddling around the Pine Island section instead, staying one night in a fancy lodge and the second in a rental cottage at the other end. A driver will take us back to our car and we’ll cover the next leg to Fort Myers in our Prius. We’re only here for the weekend, so I have to be content with a Calusa taste instead of an immersion.

The night at Tarpon Lodge is dreamy, I have to admit. There’s a perfect sunset from the room balcony with a drink in hand, then an elegant dinner in their restaurant on the water. We sleep soundly in a comfortable bed.

kayaking among mangroves along Pine Island in Florida

Paddling Into the Blueway

After an early breakfast, Gulf Coast Kayak drops off our transportation and we launch into the water for a day of slow transit. The Calusa Blueway is named after the native American tribe that dominated what is now southern Florida when the conquistadors showed up. They did not roll out a welcome mat for the invaders and put an end to Ponce de Leon in a hurry. You can’t blame them: they had already been here for thousands of years, living off the land and just taking what they needed.

The "Florida Crackers" moved in next though and by the mid-1800s few Calusa remained, having died from foreign disease, being killed in the Seminole Wars, or having seen what was coming and sailed off to Cuba. Fort Myers eventually became a cattle town, the main hub of the region. Pine Island stayed sparsely populated most of that time, however, not seeing much more than occasional fisherman until a bridge to the mainland went up in 1920.

This is the largest island in the area but one of the least-known since it is mainly residential. Most of the tourists looking for sun and fun head to Sanibel Island, Captiva Island, or Fort Myers Beach. Those with lots of wealth or their own boat head to more obscure dots on the map such as Useppa, Cabbage Key, or Cayo Costa.

We secure a duffle bag on the back of my kayak, snap bungee cords over our water bottles, and glide out into the Gulf of Mexico.

An anhinga “snake bird” nods its head up and down as we glide by and I’m guessing it’s some kind of defense move. This species seems to be the inspiration for the word “birdbrain” though: it seems perpetually perplexed and physically its brain can’t be any larger than a grape. It glides through the water like a reptile though, getting plenty to eat and then perching in the sun to let its feathers dry.

Osprey in a tree along the Calusa Blueway, Pine Island

We soon come upon plenty of other birds to check out though, and in Florida they’re neither tiny nor hidden. This is the kind of birdwatching meant for the traveler rather than the obsessive birdwatcher with a powerful scope. We paddle close to the mangroves where there are dozens of pelicans perched in the trees, then see several ospreys protecting their nests at the tops of different trees. In the distance white pelicans glide parallel to the water, occasionally rising up and then dive-bombing down as a school of fish gets close to the surface.

Eventually we get into a groove and it’s just the sea, our bodies, and the paddles. It’s easy to forget the motion after a while as it becomes a muscle memory. I daydream and let my thoughts wander, realizing after a while that I’ve moved a mile along the shore without really noticing.

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