Everglades Challenge 2024

Holopuni “Heihei”

Model: Mark III

Built: 2023 in New Zealand

Homeport: Biscayne Bay Yacht Club, Coconut Grove, Florida

Event: WaterTribe Everglades Challenge (Fort De Soto to Key Largo, Florida)

Crew & Tribal name: Michael Lingswiler (Halfbaked), Tom Bremen (Clacker)

Crew hometown: Miami, Florida

YouTube video of Holopuni Heihei’s Everglades Challenge.

Story by Michael Lingswiler

Being born and raised in Miami and lucky enough to be brought up on Biscayne Bay, I have owned and sailed plenty of sailboats through the years. When I sold my last boat, I was looking for something different. I became hooked on the Holopuni years earlier after browsing the internet and seeing videos of these magnificent craft sailing in French Polynesia and Hawaii.

I purchased a Holopuni after years of questions to Nick and finally winning my internal debate of whether to buy a canoe that I have never actually sailed. The canoe arrived late in November and was splashed for the first time in December. I was having a blast getting to know the canoe in my home waters but as with most things worth learning, the process was humbling. The folks at the yacht club bar certainly had some entertainment watching a person that never held a paddle in his hands attempt to helm this wonderful craft through the mooring field. None the less, by the end of January, I foolishly thought it was time to enter the Everglades Challenge.

The Everglades Challenge is an unsupported, expedition style, adventure race for kayaks, canoes and other small sail and paddle craft. Each participant is required to sign up using a tribe name. The general course of the event follows the SW coast of Florida from Ft. Desoto, down to the bottom of the peninsula, and then across the Florida Bay to Key Largo. The distance is approximately 300+ miles and you have a maximum of eight days to finish.

The event mandates an unassisted launch from above the weed line at Fort Desoto beach then check in at Englewood, Chokoloskee, Flamingo and then finish at Key Largo. To accomplish this, there are multiple choices of routes. One can travel either outside or inside the barrier islands along the West coast of Florida. The decision must also be made as to whether to travel down the Wilderness Waterway that is South of Chokoloskee and then chose the best route through the many passes across the shallows within Florida Bay.

The typical participants of this event range from world class sailors and paddlers to folks like myself that reside at the less experienced end of the spectrum. We had completed this event in a Sharpie type sailboat four times in the past. The last time was approximately five years ago. This allowed just enough time to pass to forget everything previously learned about what not to do.

Tom Bremen graciously accepted the position as my partner for this voyage. He did the other Everglades Challenges with me in the Sharpie. Although neither of us had canoe experience, he is a second-generation sailmaker with countless hours on the water. There is really no one better to have on any craft and was lucky to have him to carry me along again.

Tom (Tribe Name-Clacker) and I (Tribe Name- Halfbaked) readied the canoe with all the required safety, navigation and camp gear and trailered it from Miami to Ft. Desoto for check-in and setup.

Holopuni Heihei all packed up in Miami and ready to leave for Ft. Desoto. From left to right: Joe Kolish- AKA Firewater (drove with us and sailed on a Windrider 17), Myself-Mike Lingswiler, AKA Halfbaked, Jill Bremen-AKA Clacker’s Wife, Tom Bremen- AKA Clacker

Since we had done the event prior, check-in was a relatively easy process consisting of checking for a proper setup of our life jackets, flares, PLBs, whistles and knives. You also must demonstrate that you can open the knife with one hand, and this is typically my first challenge of the event. First time participants are required to go through a more rigorous check in process.

All the participants proceeded to unload the boats onto the beach after check-in. Once we unloaded, we spend the rest of the day rigging the canoe and talking to other participants and spectators. There was plenty of interest in the Holopuni. Many questions were asked of the lashing process. I really did not have the courage to tell anyone it was only my second time performing the procedure and did my best to speak with authority on the topic. Unfortunately, one visit to any picture of the lashings on the Pacific canoes would reveal my newcomer status.

Assembling the canoe the day before the start at Fort Desoto Beach

What was even more telling of this status was the presence of port and starboard rudders mounted to the canoe. Given our limited experience, I was worried about our ability to paddle steer the 300+ miles and therefore affixed some old multihull rudders to the canoe hull using the outboard bracket mounting tube.

The next day, after morning roll call, the start commenced just after dawn.

Day 1: Morning roll call before start of challenge

Day 1: The EC2024 participants lined up on the Fort Desoto beach waiting for the starting horn to sound

The first checkpoint was Cape Haze Marina in Englewood, Florida and just over 50 Miles to the south. Our plan was to go outside the barrier islands and come into Cape Haze through Stump Pass. There was a light breeze of about 3-5 knots out of the Southeast. It was a beautiful day, but progress was slow. We spent some time exchanging tacks with the Crazy Russian on his shunting proa and Floridaman in his Weta trimaran.

Day 1: Exchanging tacks with the Crazy Russian (right) on his shunting proa and Floridaman (left) in his Weta trimaran

These competitors were sailing solo. It is quite impressive how these participants keep up the sailing alone night and day over the 300+ mile course. Soon night fell and we lost track of our fellow participants. The wind remained light throughout the night, and it was dawn before we finally approached Stump pass.

The “Crazy Russian” on his shunting proa Drama Queen (YouTube video here)

Stump pass can be notoriously rough if you have a swell running and an outgoing tide. In addition, if you are unfortunate and approach on a strong outgoing tide, it can be a challenge to make way, and some end up walking their craft along the beach into the cut. We came in early on the outgoing tide cycle and were able to sail without much issue into Cape Haze Marina. We pulled into the marina with the Crazy Russian. We signed the check-in sheet, used the facilities, grabbed some noodle soup, and cast off for checkpoint two at Chokoloskee.

Chokoloskee is just over 100 miles from Englewood, within an area called the 10,000 islands and within the Everglades National Park. Chokoloskee has a very interesting history. Pre-European settlement of Florida had this area home to the Calusa Indians and many of the shell mounts from this era still exist. There are also a few very interesting books detailing late 1800s life in this area. “The Story of Chokoloskee Bay” describes many of the locals of the time as “Refugees from Justice”. This is also outlined in an excellent novel called “Killing Mr. Watson”. The area also had a reputation of nefarious activities during prohibition and the 1980s.

On leaving Cape Haze Marina, we proceeded South down the intercoastal waterway for about 8 miles, then headed West out Gasparilla Pass, and then South again when we were far enough off Gasparilla Island. Once again, the wind was very light, and we were ghosting along with one of the many Graham Brynes designed sharpies that does this event. Knowing we had a long leg, Tom and I decided to start paddling a bit along several parts of the course. It was quickly determined that I don’t use these muscles near enough and this event was going to challenge my physical abilities.

We had a pleasant sail/paddle down past Boca Grande Inlet, and then past the Cayo Costa and Captiva Islands. We were accompanied by plenty of marine life as we travelled South and then by night fall, we were off Sanibel Island on port tack heading west of South.

South of Sanibel the coastline breaks away to the east. By choosing to stay on port tack, we found ourselves far offshore and downwind of the desired Indian key channel before the wind all but died. We made this same mistake in a previous challenge and should have learned our lesson then! As we clawed our way upwind to the east in almost no wind conditions, I was starting to feel fatigued and wrongly punched a waypoint 8 miles north of the intended Indian Key channel. When it was all said and done, we approached Indian Key the time of max ebb tide. We attempted for an hour to make our way against the current before just dropping anchor and waiting for the tide to turn. We slept for three or so hours before lifting anchor and proceeding through Indian Key pass to the mouth of the Barron River and turning south into Chokoloskee Bay. We landed at Chokoloskee almost 2 days after leaving Cape Haze Marina. This was about 12 hours longer than the participants that choose more eastern offshore route. Lesson learned!

Day 5: Coming into Chokoloskee Bay at the mouth of the Barron River

Day 4: Pulling up to checkpoint 2 in Chokoloskee- Lucky it was high tide otherwise we would have to slog through a 100 yards of knee high mud to get to the sign in sheet

We choose only a short stay at Chokoloskee to sign the log and restock our water supply. Many participants take their time to run the course of this event. They will camp at many of the isolated beaches and islands or stop and eat at some of the restaurants or even check-in to hotels along the way. In this and the other EC events that we have participated, we have always just kept moving. I can’t explain why, except there was always a feeling that someone is going to pass us.

South of Chokoloskee to Flamingo there is almost no development and allows one an opportunity to see some of the Everglade’s wildlife. Seeing this area, it was easy to picture what South Florida was like before the overpopulation that plagues it today.

Day 5: Leaving Chokoloskee - A Fish Hawk and Ibis looking down and admiring the Holopuni. I was once told that the Ibis was the last bird to leave for shelter before a hurricane hits

Leaving Chokoloskee, you have the option of traveling down the wilderness waterway on the inside. This route takes the traveler through the Southwestern side of Everglades National Park and allows participants to experience the wonders of the Everglades.

The Everglades are a network of wetlands and forests fed by a river flowing out of Lake Okeechobee, southwest into Florida Bay. The Everglades National Park was established in 1947 to protect the Everglades Ecosystem which covers 1,508,976 acres. The Everglades is best described in Marjory Stoneman Douglas’s book, The Everglades: River of Grass, published in 1947. It is no coincidence that this is the year the park was formed. She championed the establishment of the park, as well as many other very worthy causes in her 108 years on this earth.

Day 5: Leaving Chokoloskee out Rabbit Key pass

This Wilderness waterway route will leave you on the Freshwater side of Flamingo and will require a short portage to the Florida Bay side before traveling to the finish. Event rules require this portage to be unassisted and the participant must carry all carts or needed gear with you the entire trip. We didn’t want to carry a beach cart and opted for the 70-mile outside passage to Flamingo. In addition, we were unfamiliar with the Wilderness Waterway route and unsure if the entire waterway could support the beam of the Holopuni.

Day 5: Sailing near Pavilion Key after leaving Rabbit key pass

On departing Chokoloskee, we exited Rabbit key pass, traveled South close to the shoreline, and onto Cape Sable. From there we headed East toward Flamingo. Again, three to eight knots of Southeast breeze prevailed as we departed. It was a beautiful sail just off the beach with a perfect view of some entirely isolated places.

As we worked our way south, we exchanged tacks with Wildblue and Skinnygenes on their Core Sound 20. We rounded Cape Sable just after dark and turned more eastward to make our way toward Flamingo. A small frontal system was coming down the state and the wind pickup up to about 15 knots but was still very much on the nose.

Cape Sable marks the western edge of Florida Bay. The Florida Bay is a large, shallow estuary with many shallow banks. The banks separate the bay into basins. The area is an important estuary as enormous sheets of freshwater flow south from the state of Florida, through the Everglades, and meet the salty water of the Gulf of Mexico. There area has strong tidal currents. With the bay’s shallow water and the SE breeze, a short steep chop was present off Cape Sable. The Holopuni’s ability to handle these conditions thoroughly impressed its occupants! There was no pounding and the canoe just sliced through the chop with ease. My only worry was the lashings done by the novice rigger but again no issue! The Flamingo checkpoint was about 15 miles from Cape Sable.

Once again fatigue was setting in and worse than any time before. Both Tom and I were hallucinating. It was a very odd sensation. You are somewhat aware that the things you are seeing aren’t real and you try to ignore them. One of the hallucinations that prevailed had me helming the canoe down a narrow canal with trees on both sides. I’m telling you that if I would have reached out, I could have touched those trees. Later in the trip, Tom and I realized we were having the same hallucinations. I’m sure somewhere there is a published scientific study on why this happens, but I find it extremely strange!

We were continuing toward Flamingo when an intense electrical storm associated with the front was noticed in the distance. A short time later, the wind died in its eerily typical way before a blow, warning us that this storm packed some wind. Looking at the GPS with bleary eyes, I saw us three miles from Flamingo. Not wanting to navigate the shallows that are present outside the small harbor during a storm in the night, we decided to anchor and wait it out. Once the anchor dropped the wind kicked up to 20+ knots with pelting rain and heavy lightning crashing around. I was so exhausted that I quickly fell asleep through all of it and woke up with no wind and the sun just over the horizon. The worst part was that I totally misread the GPS and found we anchored seven miles from flamingo not three. Now with no wind we didn’t get into flamingo till late morning. We were escorted into the harbor by a school of dolphins driving bait fish into the shallows where their breakfast was more easily caught.

Day 6: Sailing into Flamingo checkpoint with our dolphin escort

We checked in at Flamingo and again used the park’s facilities and grabbed a very nourishing ice cream bar at the convenience store. We sat for a bit to discuss our strategy for the final leg across Florida Bay to the finish. This leg has been notoriously difficult for us in past events. The choices are to attempt to choose and navigate the great many passes through the shallows into Key Largo. The shortest of these routes is mostly an easterly course and about 35 Miles. Another choice is to sail south and east through and to the bottom of the yacht channel close to Matacumbe Key and then back up to the North into Key Largo. This route typically doubles the remaining miles to the finish. The direct route is difficult if the wind is out of the East, and depending on the tide, the current can run against you with significant velocity. One year we attempted this only to find ourselves backtracking some 15 miles to find a more southerly route. Our past experiences obviously made us very wary of this leg.

The decision for this year was made difficult by the fact that the wind was south of east as if to be calling us to the shorter route. Ultimately, we believed this calling was, as Clacker put it, “a trap” and decided on the long route. This route was deep and lit up with channel markers for its entire course. We were tired and didn’t have enough energy for any additional challenges. We left Flamingo shortly after noon and as we hoped, had an uneventful light in air sail to the finish. We arrived at just after first light and just shy of 5 days after the start.

Day 7: Ghosting into Key Largo for an early morning finish

Although we finished the event, the adventure was not quite over. The challenge is a logistical nightmare for us as we didn’t have shore support moving the car and trailer along the route with us. While we made it to Key Largo, the car and trailer were still at Ft. Desoto. Some participants leave their boats in Key Largo, arrange for transportation back to Ft. Desoto to get their vehicle, drive the five hours back to Key Largo and pack their boats onto trailers. We opted to sail another 40+ miles back to Coconut Grove where we launch. We left the beach cart there on our departure to substitute for the trailer that was still in Ft. Desoto.

Day 7: The customary “finished” photo. About this time, you swear you’ll never do this again, but you still come back the next year. A good friend told me once “It’s got to suck a little to be memorable!”

We showered, changed, grabbed some breakfast at Ms. Mac’s and then left Key Largo for Coconut Grove late morning. This was the best sailing of the trip. Traveling north now, the wind was finally behind us at 10-12 knots, and we were sailing nicely through the several creeks, into Card Sound, across the shallows of Midnight pass and into Biscayne Bay. Just before arriving in Coconut Grove a light rainstorm came through to wash the sail as if to say “Welcome Home”. We arrived to the dock exhausted at about dusk. Immediately upon pulling up to the dock and never failing to provide the yacht club entertainment, I accidentally fell into the water.

Day 7: Heihei put to bed at Biscayne Bay Yacht Club, Coconut Grove after the beautiful sail home from Key Largo

It was a trip of learnings, and we had a fantastic time. It was close to five days used to get to better know the Holopuni!

Selfishly, I would encourage other Holopuni’s to participate in future years as I would enjoy learning from those with more canoe experience. I also need the encouragement to ditch the rudders! If we could get enough to participate, I’m sure the organizers would create a class for us. What do you think, will there be a Holopuni class next year?

Thanks to Tom for carrying me through this event and thanks to Nick and the Holopuni team for a beautiful canoe and all the encouragement!