Nature + Recreation

Here’s How an Ultra-Marathoner Explores SWFL

Follow the 80-mile trail from Naples to the Sanibel Causeway and back through the eyes of local ultramarathoner Jamie DePaola.

ultra-marathoner Jamie DePaola
Ultra-marathoner Jamie DePaola (Photo by Brian Tietz)

“Running isn’t my escape. It is a way to connect to myself and to the world. When I moved to Naples 10 years ago from Maryland, running became a way for me to tour the town without being bound to a car. I’d started running in 2009, around the time my college gymnastics career was ending. I loved discovering new shops, trails and hidden beach-access points. I would venture from my place at Saint Croix apartments in North Naples to the corner of Livingston and Immokalee and up to Coconut Point, or sometimes from Vanderbilt Beach Road down to the beach, following the shoreline or through CREW Bird Rookery Swamp, which is always lit up with wildlife. 

Since then, I have put in about 20,000 miles—and counting—on foot. In October, I’ll be doing the Gulf to Gulf 80-Mile Relay Race solo (aided by a support crew) as an ultrarunner. My goal is to complete the course—from Naples to the Sanibel Island Causeway and back—in about 25 hours. The route is near and dear to me; I’ve run the entirety and portions of it numerous times, and I’ve seen so much beauty in all areas of the run. It’s a great way to see a large swath of Southwest Florida.

I start at Cambier Park around 5 a.m. before the sun comes up. I smell the sweet earthiness of the dewy grass and the rich, nutty aroma flowing from a nearby coffee shop. It smells like a new day, a familiar scent to many runners. Running through Fifth Avenue South, I’m transported to the small Maryland town where I grew up and feel a sense of nostalgia. Much of the first part of the run stays off the beaten path and close to the beach on Gulfshore Boulevard and then onto Crayton Road, where you pass fairytale homes and familiar faces on their morning runs. I can hear the beach throughout much of the trek, and the sound of the waves soothes my mind when I start getting restless, whether it’s at mile 5 or 55. 

By the time we get to Pelican Bay, the sun is coming up. The canopy of trees provides ample shade, and there are tons of butterflies—the area is so green and secluded. After developers created Pelican Bay in the 1970s, they opted to protect much of the mangrove forest, making this a haven for runners and cyclists. It’s especially beautiful in the early morning. From there, I cruise onto Vanderbilt Drive and take back streets toward Bonita Beach Road. This low-traffic area has charming beach houses and wide sidewalks, so I don’t have to worry about traffic or where I’m going. I can put my brain on auto-pilot and conserve energy—you have to rest your mind as much as your body on long-distance runs.

Running is a very spiritual experience in that way. You get this euphoric sense when all of you—your heart, your body, your mind—are in tune with each other. It’s a raw emotion, made even deeper because I find myself immersed in our area’s natural surroundings. It’s also very whimsical. Your senses are so heightened—you hear the birds differently. Trees look bigger. For me, it’s more about the journey than the finish line, and I like to take the time to enjoy small moments throughout. I might stop and watch the egrets or let the butterflies land on me.

Running down toward Barefoot Beach on Bonita Beach Road is awe-inspiring. The bridge curves around, and suddenly you’re still on the highway, but you see the beach stretch out in front of you. You don’t get that anywhere else in Southwest Florida. The sand is so white. The water is bright turquoise. The palm trees line up so perfectly, the whole scene looks like a postcard, especially by the time I get there in the afternoon, and there are people laying out and swimming on the beach and fishing off the bridge.

The entire stretch from Lovers Key State Park to Fort Myers to the Sanibel Causeway runs along the water, with Estero Bay to the east and the Gulf of Mexico to the west. I love all the bridges—it’s like I’m walking on water. Plus, the wildlife is fantastic—the dolphins and pelicans near Delnor-Wiggins Pass State Park, the manatees around Lovers Key State Park. Sometimes, when I’m looking down, I can see pockets of clear water with the manatees’ glittering trails. I take my time running near Lovers Key’s shady trails and keep an eye out for bigger wildlife like bobcats. I see tons of pelicans, egrets, anhingas with their wings stretched out like superheroes, and turtles, which are often lying on rocks, sunning themselves. Ducks are my favorite, and I see them everywhere on this route, crossing roads, on the street, on people’s lawns. I love how they travel in packs and how funny they look when they run. 

As you go up the bridge into Fort Myers Beach, you start seeing brightly colored buildings, some kitschy shops and restaurants, and tiki bars. It’s devastating to see the damage that remains after Hurricane Ian. In some areas, the piles of debris are taller than me. But it also gives me a sense of strength to think how hard these people fought—and keep fighting. It inspires me to keep going.

It’s late afternoon by the time I get into Fort Myers Beach, and the restaurants are alive with people having a great time. The kids lined up outside of Royal Scoop, friends and families eating on the upstairs deck at The Whale, even the partyers at Lani Kai Island Resort—it can be really nice to have the energy of a crowd when you’re more than 30 miles into a run. 

Matanzas Pass Bridge, leaving the beach, is one of my favorites. It was the tallest bridge in Fort Myers when it was built in 1979. It’s challenging, for sure—you’re 35 miles in and staring into the sun—but it feels so rewarding to cross over. You see Dixie Fish Co. and Doc Ford’s ahead, and you know you’re almost to Sanibel.

At about 5 p.m., I hit the Sanibel Causeway, the halfway point, and my reset. By now, I’ve been running for almost 12 hours, and I’ve seen an amalgamation of cultures and generations across the Gulf as I move from higher-end Naples to charming Bonita Springs to naturalist Lovers Key to lively Fort Myers. And you can see all of this in one day—how special is that?

I take a moment to acknowledge the miles I just completed, and I treat the way back like a completely separate run. I may even brush my teeth and change into new shoes and clothes to compartmentalize. The route is the same, but I have a different perspective, and my team is leapfrogging me more frequently.   

I take in the cotton candy skies as the sun starts to set, and I return through the stretch of beaches I passed earlier in the day. On Fort Myers Beach, people are gravitating toward the shore to watch the sunset. I soak in those last few minutes of twilight through Lovers Key State Park, where the cicadas are now chirping like a symphony before the world goes dark.

By the time I get back through Bonita and into the Vanderbilt area, it’s well into nighttime. I see the last lights go out in people’s homes and imagine the lives within—it’s a creative moment
for me.

Running at night is a whole different animal. I have to focus extra hard on paved sidewalks like around Pelican Bay, where there are roots I could trip over. The plentiful lights around Waterside Shops help light my way, but the sights and sounds of animals that were so amazing during the day can be eerie now. It’s like I’m on guard for what could be coming out of the trees. I would be lying if I said I wasn’t scared for those eight to 10 hours I’m running in the dark. But sometimes, the things that are the scariest and that we overcome anyway are the most enjoyable. The night parts are so vivid because I’m so alert, even when I’m fighting the sleep around 2 a.m., still 10 miles from the finish line.

Running back through Park Shore and Moorings during the October relay, I like to see the Halloween decorations, which can be excessive in some places—it’s so fun. If there’s a bright moon, the glow offers a sense of peace, and I take each thought and emotion as it comes. Each mile is a mile closer to the finish line where the coffee aroma, dewy grass and my crew greet me—25 hours later.” 

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