This past March 4th, Diego Caputi and I embarked on an expedition-style race, open to non-motorized small vessels powered by the wind and/or paddle. The Everglades Challenge, first raced in 2001 and running for the past 22 years, is organized by The Water Tribe, led by Steve Isaac, also known as “The Chief.” This event is renowned as North America’s toughest small craft competition.

The challenge entails sailing or rowing approximately 300 nautical miles, starting from Fort Desoto in Tampa and ending at Pelican Resort in Key Largo. Participants must make stops at three checkpoints: Cape Haze Marina, Chokoloskee, and Flamingo, following a north-to-south route. While you are given 8 days to complete the task, most participants finish within 3 days.

Discovering the Everglades Challenge: A Journey into Adventure

Back in 2013, as the summer camp coordinator for Sail Laser Miami, I stumbled upon an intriguing event that would captivate my imagination. Two ambitious high school sailing instructors, Diego and Giancarlo, caught my attention with their love for sailing in Biscayne Bay and their thirst for adventure. Little did I know that a simple conversation with Diego would set the stage for an extraordinary journey, unfolding a decade later.

We made a resolute decision to tackle the legendary number 6, a Hobie Cat Getaway adorned with wing seats, renowned for its countless thrilling voyages across the vast waters of Biscayne Bay. To commemorate this remarkable adventure, I eagerly ordered a new jib, a symbol of our dedication and passion. It was essential to outfit the sail with two reefing points to meet the event’s requirements and ensure our participation in this exhilarating challenge.

Join me as I recount the exhilarating tale of our Everglades Challenge adventure, where dreams transformed into reality, and a passion for sailing ignited an unforgettable journey through the untamed beauty of the Florida wilderness.

Essential Gear for a Successful Journey

With the deadline to subscribe to the race approaching on January 31st, we had ample time to meticulously prepare ourselves for the epic adventure that awaited us. Diego, being the dedicated and thorough planner he is, immersed himself in research, devouring logs and videos to gain valuable insights into what it takes to not only complete the race but to do so competitively.

One crucial lesson became evident: to finish within a reasonable timeframe, sailing day and night without stopping was imperative. This realization led us to invest in a game-changing item—the marine beany bag from West Marine. This versatile and comfortable seating option provided much-needed relaxation during off-duty hours at the helm. We also prioritized the comfort of the on-duty captain by purchasing a padded folding seat, ensuring their four-hour shifts were as comfortable and supported as possible.

Of course, numerous other gear items proved essential for a successful journey. We equipped ourselves with a Spot X device to track our progress, Epirbs for emergency situations, a comprehensive set of tools and extra cables for any necessary repairs, life vests for safety, a trusty pocket knife, two dry boxes for waterproof storage, dehydrated food for sustenance, a reliable jet boil to prepare meals and hot beverages, energy-boosting snacks, foul weather gear, cozy sleeping bags, a heavy-duty tarp to shield us from rain, navigation lights, a VHF radio for communication, charging devices for our phones, a selection of books for reading pleasure, and a portable speaker for enjoying podcasts or music along the way.

By ensuring we had all the necessary gear, we set ourselves up for a safe, comfortable, and successful journey through the challenges of the Everglades Challenge. Join us as we embrace the spirit of adventure and navigate the unpredictable waters with confidence and preparedness.

The Start of the Adventure

The adventure started on Saturday March 4th to much anticipation and joy. There is something amazing about the camaraderie among the participants and the feeling of always being on the move. There are long stretches of open water sailing across Tampa Bay, Pine Island Sound, and the Gulf of Mexico to keep a sailor busy and entertained. The first day of the voyage is pleasant enough and we decide to take the intercoastal due to windy conditions out on the open Gulf. Not everything is stress-free in the protected waters of the intercoastal and sailing under the first bridge was nerve-racking as the wind was partially blocked and we had to fight a stiff current. The bridge attendant almost did not want to open the bridge because we were under sail and we had to tell him we had an outboard aboard and would use it if necessary.

First Check Point

After the first check point at Cape Haze Marina, we continued sailing down the intercoastal approaching Charlotte’s Bay and Pine Island Sound. Before entering the bay, we were confronted with the sad reality of the red tide. There were dead fish everywhere from there all the way to Sanibel Island and well into the Naples area. In the intercoastal, it was particularly heavy and it would irritate your throat and nasal passages.

Charlotte Bay is always a great sail as the narrow intercoastal opens up into a wide body of water with plenty of room to sail in deep reaches. Our first night in the water had a nice breeze, and we were moving at a good speed. At around 1 am, we were within reach of the Boca Grande Inlet, a massive inlet that connects Charlotte Bay and the Pine Island Sound with the Gulf of Mexico. To our delight, there was an outgoing tide and a nice northwesterly breeze that would make crossing the inlet easy and sailing down the coast very pleasant.

The trip was punctuated by moments of utter awe and amazement that had one feeling giddy as a child. Coming out of the Boca Grande inlet was such a moment. Under the glare of almost a full moon, we could see massive swells moving towards the coast. You felt small up against these swells, and they seemed like they would swallow our little vessel, but our confidence grew as our little boat bravely climbed these swells, and thank God, they were uniform in size and never threatened to crash over us.

Most of the night was uneventful, and by morning’s light, we were rounding Sanibel Island. At dawn, we saw two boats of fellow contestants, including the winning vessel.

Second Day on the Water

The second day was a rather long one. It started off the coast of Sanibel Island, and we finished anchored at Indian Pass and the entrance to Chokoloskee. The sail from Fort Myers to Marco Island is long and boring. We kept ourselves busy by reading pirate stories, napping, and eating. The scenery didn’t change much here, with condominiums sticking up from the shore to our left and wide-open seas to our right.

However, we did get to enjoy the most amazing sunset as we were about to round Marco Island. The wind picked up, and we were sailing at a good speed of 7 to 9 knots. With night approaching, we would take out our headlights and coats, put away our hats and sunglasses, and settle in for a night of sailing. We came to appreciate sailing at night as it offered a break from the sun and the heat.

As we rounded Marco Island, we entered the Everglades part of the Challenge. The condominiums and towers gave way to mangrove islands and mangrove channels. It was a welcomed change in scenery, but one we would soon regret.

Attacked by Mosquitos

As we entered the mangrove channels, the wind died down and the sounds of the ocean faded, leaving us in a quiet calm. We started rowing, but then something terrible happened. A swarm of mosquitoes, perhaps around 1000 of them, formed a dense cloud and began attacking us from every direction. It was a desperate and overwhelming experience that triggered a fight-or-flight response. However, there was nowhere to escape but to move forward. We rowed for about an hour, battling through this mosquito cloud that seemed to be devouring us alive. Despite covering ourselves with long pants, jackets, and gloves, the mosquitoes still managed to find any exposed skin and leave their bites.

This encounter with the mosquitoes shattered our spirits, and we seriously contemplated giving up, sailing back to Marco Island, and calling it quits. However, after some rational thinking, we decided to persevere once we managed to distance ourselves from the relentless mosquitoes. In fact, we even sailed in the wrong direction for about 30 minutes in an attempt to leave them behind.

We were so disheartened by the experience that we didn’t even bother making dinner that night. As the hours passed, we noticed that we were getting closer and closer to Indian Pass, the entrance to Chokoloskee. This realization lifted our spirits and renewed our determination. We reached the pass around 4 am and decided to anchor for three hours to get some sleep, which was the only time throughout the entire trip that we weren’t sailing. We wanted to wait for the sunrise, both to avoid the mosquito menace and to take advantage of the incoming tide that would carry us into Chokoloskee Bay!

Start of the third day!

Indian Pass is a picturesque channel that meanders through untouched mangrove islands, offering us glimpses of abundant wildlife, including playful dolphins and a diverse array of birds. As we ventured further inland, the wind gradually subsided, necessitating an hour of rowing in Chokoloskee Bay to reach the second checkpoint.

Chokoloskee is a charming location where we took the opportunity to refresh ourselves. We indulged in an outdoor shower, brushed our teeth, and tidied up a bit. To satisfy our hunger, we decided to have lunch at a nearby restaurant, which exceeded our expectations with its exceptional food and service. While we waited for the outgoing tide at Chokoloskee Pass, we soaked in the pleasant atmosphere.

With the anticipation of the tide turning in our favor, we embarked about an hour before its shift. However, sailing out became a daunting task as the channel narrowed, and a powerful current impeded our progress. Despite the initial struggle, the turning of the tide eventually granted us the opportunity to set sail into the vast Gulf of Mexico, aiming for Cape Sable.

The greatest afternoon of the Adventure!

As we departed from Chokoloskee Pass and ventured into the vast expanse of the Gulf of Mexico, we were greeted by a strong and steady westerly breeze. The wind blew at a speed of 15 to 18 knots, allowing us to sail comfortably on a broad reach. The increasing wind generated substantial waves, reaching heights of approximately 4 feet. Riding these waves became an exhilarating and nerve-wracking experience as our boat would be lifted and propelled down the face of each wave.

Those 4 hours of sailing were undeniably the most thrilling and intense moments of our entire journey. We were soaring through the water, maintaining an impressive average speed of around 10 knots. It was a captivating fusion of sailing and surfing that will forever be etched in my memory.

As night descended, the wind subsided but remained consistently favorable. Around 11 pm, we successfully rounded Cape Sable and treated ourselves to a well-deserved dinner. With the help of our trusty jet boil, we prepared a delicious meal from dehydrated ingredients. As the wind calmed further, it took us a few additional hours to complete the last leg of approximately 10 miles, finally arriving at our third checkpoint: Flamingo Everglades Visitor Center and Marina.

The Final Hours of the Journey

Upon reaching the third checkpoint at around 2 am on Tuesday morning, our initial plan was to rest and sleep. However, we quickly realized that the area was infested with mosquitos, and lacking a tent for protection, we made the decision to return to the water. Following the lead of two other vessels, we set off again around 3 am. To ensure we had some comfort during the night journey, we prepared a much-needed thermos of soothing green tea.

Navigating through the shallow waters of Florida Bay, we followed a Nacra 20 catamaran and a small ketch. Despite having read accounts of traversing Florida Bay, it was challenging to fully comprehend the experience until we were actually there.

Florida Bay revealed itself as a pristine environment brimming with life, characterized by its incredibly shallow waters, often only 3 feet deep even at high tide. The bay was adorned with picturesque mangrove islands. To navigate this spectacular area, we had to follow a natural but narrow channel marked by small wooden posts. These posts are diligently maintained by the National Park Service.

Embarking on this final leg of our journey at 3 am, we felt a surge of excitement knowing that we were merely 40 miles away from the finish line. Following the lead of the two boats ahead of us provided encouragement and reassurance.

Switching on our red light headlights, we illuminated our path as the reflective tape on the wooden stakes gleamed red in the light. All of this unfolded under the captivating presence of a full moon, occasionally concealed by low-lying clouds, casting an enchanting aura over the bay. The combination of dim light and the red glow of our headlights reflecting off the stakes created a truly magical and exhilarating atmosphere.

This particular night proved to be the most extraordinary and captivating experience of our entire journey, leaving us in awe of the beauty and wonder that surrounded us.

Final Morning Arrives

The final night gracefully gave way to an awe-inspiring sunrise, painting the sky with vibrant shades of orange and pink. As the sun began its ascent, casting a mesmerizing glow, we were treated to a magnificent spectacle. Meanwhile, the moon, magnified by the atmosphere, slowly faded into the light of the day, creating a surreal scene of a pinkish-violet sky. This breathtaking moment is etched deeply in my memory and will forever remain unforgettable.

As morning unfolded, the transition from darkness to light revealed the presence of wildlife around us. We witnessed the graceful movement of stingrays gliding through the water and encountered an area teeming with nurse sharks. Throughout the night, we made significant progress, steadily catching up to the two boats that had been leading the way. Following their path out of Flamingo proved to be a wise decision, propelling us closer to the finish line.

The final leg of the race was filled with excitement and anticipation. During the traversal of Manatee Pass, a narrow and challenging channel, a thrilling moment arose. Despite the headwind against us, we harnessed the power of our two reliable oars, enabling us to row through the channel. In contrast, the Nacra 20, equipped with a smaller oar, had to alter their course and navigate around several mangrove islands. This temporary advantage allowed us to briefly surge ahead of them!

Ultimately, they crossed the finish line 10 minutes ahead of us, partially owing to their use of a spinnaker sail, which we did not possess. Nonetheless, the conclusion of the race was exhilarating, filled with fierce competition and a sense of accomplishment for all involved.

Conclusion

I cannot be prouder of what we did with @dcaputi93 this past March. We completed the Everglades Challenge, a sailing marathon of roughly 300 nautical miles from Fort Desoto to Key Largo, and did it in 3 days and 15 minutes, ending in 10th place overall out of a field of 71 boats.

The feat was nothing short of miraculous considering that we were up against boats that were way faster and bigger than our little Hobie Gateway, the famous number 6, that has taken countless children and adults across Biscayne Bay! But it should be known that it was a bit more than pure luck, and rather a bunch of preparation, studying the best strategy, and making several correct decisions throughout the race!

I want to thank Diego for all his hard work researching the race and what it takes to finish in the top 10 (something he predicted we would do). He also put in some long hours at the tiller and was constantly pushing to keep going even when we were tired, cold, and wet!

I also want to thank watertribe.com for organizing the event and @cgscyouthracing for the cordage and the support!

The adventure was nothing more than epic and well worth it! I feel totally empowered by what was achieved and putting an end to the endless debate that small vessels can complete big journeys. The adventure of a lifetime is within everyone’s reach! Can’t wait to complete it next year!