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Kayak Time Machine

Grab a kayak and explore the Calusa Blueway near Sanibel to catch a glimpse of Old Florida.
Story and photo by Ed Kiggins

At any given time in any given beach town in Florida you can find him. An older, perpetually tanned gentleman, he calls himself a native Floridian even though he’s likely a transplant from the frozen north. Regardless of the purity of his credentials, he knows his adopted hometown well and is eager to share that knowledge with anyone he senses to be the least bit interested.


Above: A pergola frames a pathway the leads to the water and beach.

In Title: The Castaways resort had a selection of kayaks suitable for exploring the Calusa Blueway.

Below: White pelicans stop to fish and rest along the Blueway near Sanibel during their migratory route.


Half nostalgia/half tall tales, he openly professes his love for the days when the horizon stretched out in all directions, unbroken by modern dalliances. When the fish jumped right into your boat. Before the big box retailers. Before the fast food restaurants. Back when you didn’t have to squint to see the true wilderness of the place. His stories are of Old Florida. What’s more bittersweet about these tales is that you don’t have to listen long to become equally nostalgic for the good old days, even though you may never have actually experienced them. Should the old man’s words get to you and you find yourself mourning the loss of that simple beauty, fear not. Old Florida is not only alive and well, it’s hiding in plain sight, on the southern gulf coast.

An overview

The Great Calusa Blueway is nothing short of a brilliantly presented last chance to behold the beauty of Old Florida as its earliest visitors likely did: from the water. Much like its hiking trail cousins, the 190-mile long Calusa Blueway is a blazed trail that literally takes paddlers on a journey from the birth of Florida to present day and all points in between. Situated along the 230-square miles of inland waterways of Lee County, the trail encompasses three distinct regions: Estero Bay; Captiva, Sanibel and Pine Islands; and the Caloosahatchee River. And while there is clear evidence of varying levels of civilization to be found along these routes, the opportunity to take in the simple, natural beauty of Florida without high rises or strip malls is what really defines the Blueway.

“If you’re looking for that Old Florida feel where you want the moss-draped oaks and the huge leather ferns and that lush greenness, you can have that,” says Betsy Clayton, waterways coordinator, Lee County, Florida, Parks and Recreation. “Unlike places up north where you have linear trails, this is more an opportunity to meander. You can do loops and through-paddles. You can paddle for an hour and feel like you’ve been gone a day or you can paddle for multiple days.”

Completed in 2007, this expansive opportunity has redefined the classic Florida experience and thrust the area into the limelight as a premiere destination for kayakers, canoeists, and stand-up paddle boarders. Enthusiasts from around the world descend upon the tiny area just off the west coast of Fort Myers to catch a glimpse at what was long thought gone.

slowing it down

The area around Captiva and Sanibel Islands–the main centerpoint along the Calusa Blueway–may best be remembered for the figures who put it on the map. Teddy Roosevelt, Charles Lindbergh, Thomas Edison, and Henry Ford all vacationed here, with Edison and Ford ultimately building their famed winter estates in neighboring Fort Myers.

Farther back along the dateline–to Really, Really Old Florida–Ponce de Leon is reported to have met his end on or near Captiva Island at the hands of the Calusa Indians. Ironically, because of injuries sustained during those prolonged battles, this area is where his quest for the fountain of youth ended.

While that fountain may never have been found, evidence of its existence can be inferred by the area’s refusal to grow up. Sanibel and Captiva remain much as they were during the times of Edison and Ford (though that lack of modernization is more likely due to the diligence and hard work of citizens, governing bodies, and an army of volunteers, all intent on preserving something they consider worthwhile). There are few if any icons of commerce in the heart of Sanibel-Captiva. Nearly everything one needs, from diapers to engine oil to fine wines, can be found in one of the two general stores. There is a single four-way stop intersection (also the hub of the local nightlife) and the speed limit is a strongly enforced 25 mph for most of the length of “the strip.” Wi-Fi is spotty and cell phone signals are hard to come by, though that’s not necessarily a bad thing. After all, this isn’t about staying connected. It’s about donning your pioneer hat and thrusting yourself back into the golden age of America. As Clayton puts it, any given day never needs to be more than “just you, the sandy bottom, the big blue sky, a bunch of jumping fish, leggy wading birds, and an opportunity to feel like you’re on your own adventure.”

delicious solitude

I set out for Captiva wanting to remain as true to Old Florida as possible. While there were some very appealing resort-style options to be had, I decided on a beachfront cottage at the excellent Castaways, just south of the causeway. Though my unit was equipped with a full kitchen, indoor plumbing and air conditioning, it was easy to imagine myself on vacation near the turn of the century. There was nothing between me and the ocean but the sand and a wood trellis (a strange formality). I enjoyed the sunset from my screened porch before heading off to bed. The next day I was to set off on my first paddling excursion, so I knew I’d need my energy.

I arose at sunrise in search of a good cup of coffee and something loaded with carbs when I happened upon a wild flock of Betsy’s leggy wading birds. Hundreds, if not thousands of pelicans coated the bay’s surface, taking advantage of the low tide and the abundance of fish to stop along their migratory route and feast. The snook in this back bay literally jumped from the water as if exposed to an electric current, often into the waiting mouth of a hungry pelican. I later learned that pelican sightings of this magnitude are fairly rare, occurring only about once a decade if that.

After breakfast, I returned to the back bay and picked out my kayak from the resort’s gratis offerings, a bright yellow 12-foot sit-on-top model. As I glided from the dock, I quickly forgot the bit of civilization I’d emerged from. Mangroves lined the waterways and, beyond the sound of the occasional snook flopping back into the water and the sound of the Blueway gently lapping at my hull, all was quiet. Ospreys tended their nests as heron and egrets went about their business. Hermit crabs scuttled about the bay floor, easily seen through the clear inches-deep water. The temptation to pick one up was strong, but these are protected waters and doing so isn’t only a bother to the hermit crab, it’s also a crime.

A short 20 minutes from my put-in point, I discovered a mangrove tunnel that rewarded me with one of the most tranquil settings I’ve ever encountered. I stayed there a while (though not nearly long enough) admiring the silence before paddling out to see if I could find a bottlenose dolphin. This section of Florida boasts one of the highest concentrations of bottlenose dolphins in the country. While that quest went unrewarded, I did manage to encounter several West Indian manatees. Having never seen one up close before, I was amazed at just how accurately they’d been described to me: playful puppies with hairy potato noses. The manatees in these waters are protected, so initiating contact with them is strictly forbidden. However, their curiosity is legendary and they are known to inspect kayakers every so often. The few I came upon seemed perfectly disinterested in me, perhaps sensing that I’d come to see the dolphin. Whatever the case, these gentle sea cows are perfectly harmless, though fascinating to behold.

During my time in Sanibel, I managed to spend about 16 hours on the water. While my core felt the tinge of an unfamiliar workout, the experience let me feeling more centered than tired. Each time I emerged from my kayak, I did so feeling only slightly weaker in my body, but infinitely stronger in my mind. Despite my deliberately not repeating any path twice while paddling, I still did not scratch the surface of what the Calusa Blueway has to offer. What’s more, the scenery never seemed redundant. Each trail has its own unique look and feel, and each offers an entirely different type of experience. For instance, the Estero Bay trail offers a range of opportunities from rare bird watching to cocktails at one of the area’s premiere beach resorts. Pine Island Sound offers not only the most “Old Florida” feel, but also boasts some of the best fishing in the country. It also provides the best opportunity for outdoor lovers to sleep under the stars. Those who prefer a more freestyle paddle will want to seek out the Caloosahatchee River Trail, where trail markers give way to GPS coordinates. A must-paddle for those seeking the ultimate in seclusion.

final tips

The Calusa Blueway is an intense visual experience that does not require any special skill or advanced training. You will not need to practice your Eskimo roll, nor will you encounter any class 5 rapids. In fact, the average depth of the water on the Blueway ranges from one to four feet. While you’re always strongly encouraged to wear a Personal Floatation Device (PFD), unless you’re 3’ 11” and can’t swim, you’re pretty safe, even if you spill. Even on windy days, the back bays remain fairly calm.

A word of warning. For all intents and purposes, the Calusa Blueway is a drug–a very addictive drug. Fortunately, the only side affects are tranquility and some of the most amazing memories you’ll ever carry with you. So the next time you’re in your favorite Florida beach town and you run into the old man, be sure to clue him in. Old Florida lives.

Ed Kiggins is creative director of AAA World magazine. He is based in Wilmington, Del.

Mar/Apr 2013 Issue


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To visit Lee County in southeast Florida, first stop by your nearest AAA service office for maps, reservations, TripTiks® and TourBook® guides.



Pointers for Paddlers

By Ed Kiggins

A word to the anglers. In the words of the great Chief Brody, “You’re gonna need a bigger boat.” The fishing in these waters is mind-bendingly good. In fact, Pine Island Sound has been ranked by Field & Stream as one of the top 10 fishing destinations in the U.S.

Two words about insects. Bring spray. “Noseeums” (tiny, biting insects) are vacation ruiners, and they are abundant in this sub-tropical climate. Without proper protection, you will be bitten in places you hadn’t considered biteable

Three letters and a number about the sun. SPF 1,000,000. Not only is the Florida sun quite strong, the breezes from the bay do a fair job at distracting one from its intensity. Paddlers are advised to wear head cover, even in the “cool” months when temps dip into the 70s.

Most resorts or hotels offer kayaks, canoes or paddle boards for their guests, free of charge. However, you’d do well to consider that this gear is more recreational and is well used. If you plan on spending more than a few hours on the water, I’d strongly recommend seeking out any of the roving outfitters in the area. They will not only bring a custom-fitted kayak and gear directly to you, but they are also capable of leading excursions for you or your group.

The Calusa Blueway app allows paddlers to research outfitters, find put-in points, check out accommodations, restaurants, maps, and more.


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