Sailing World - - Pond - BY JOACHIM ROESLER

Sail­ing down the west coast of Florida al­ways sounded good to me, es­pe­cially in March, when my al­ter­na­tives are ei­ther frost­bit­ing, driv­ing long dis­tances in search of sail­able ice or mop­ing in front of a fire­place. The Ev­er­glades Chal­lenge of­fers an ideal win­ter es­cape in the for­mat of an ex­pe­di­tion-style small- craft ad­ven­ture race for kayaks, ca­noes and sail­boats. The re­gatta — if you want to call it that — typ­i­cally starts on the first Satur­day of March. Con­tested for the first time in 2001, it has now taken place 18 times, or­ga­nized by a group calling it­self the Water­tribe. The race’s web­site is a con­vo­luted por­tal to var­i­ous data­bases, race­tracks, routes, maps, re­sults ta­bles and ros­ters, of­fer­ing a truth­ful rep­re­sen­ta­tion of the mostly lov­able, am­a­teur­ish char­ac­ter in which this or­ga­ni­za­tion in­vites like-minded en­thu­si­asts to go ad­ven­tur­ing.

The Ev­er­glades Chal­lenge has pro­lif­er­ated to in­clude race­courses in North Carolina and Florida, and even one around (as in through) the state of Florida. The $1,500 reg­is­tra­tion fee for the long­est track in­cludes a free T-shirt but lit­tle else be­yond the course sug­ges­tion and an ego-stroking “at­taboy.”

This tribe of wa­ter­men and -women was founded and is led by Steve Isaac, who fit­tingly goes by “Chief.” He’s been crit­i­cized for his au­thor­i­tar­ian style, hap­haz­ard or­ga­ni­za­tion and ques­tion­able fi­nan­cial mo­tives, but be that as it may, af­ter keep­ing an eye on this event for many years, this spring, I fi­nally com­mit­ted to en­ter­ing. The chal­lenge of mak­ing it to Key Largo on one’s own bot­tom, as well as the ca­ma­raderie among the par­tic­i­pants, is the true at­trac­tion.

All en­tries of Water­tribe events are grouped into one of six classes (num­ber of hulls, num­ber of crew, etc.). In past years, hall-of-famer and mul­ti­hull Olympian Randy Smyth has cov­ered the 300- mile course from Fort de Soto to Key Largo in less than two days, dash­ing south through the night alone on an ex­per­i­men­tal boat called Siz­zors, a shal­low- draft shape- shift­ing car­bon-fiber tri­maran you have to see to be­lieve. This year, he has a new ver­sion, pow­ered by a semisolid wing sail.

Other crewed beach cats and tri­marans also reg­u­larly cover the full dis­tance in 48 hours or less. Crewed mono­hulls, cus­tom and off the shelf, of­ten do well too, fin­ish­ing the course in less than three days. A few of the mono­hulls have suf­fi­cient open-wa­ter­sail­ing ca­pa­bil­ity, and prac­ti­cal han­dling when in shal­low ar­eas or be­calmed. They also of­fer rea­son­able pro­tec­tion for of­fwatch crew and com­fort at an­chor. Ho­bie Tan­dem Is­lan­der ro­to­molded tri­marans, sailed hard and through the nights, have also made it to Key Largo in less than three days.

Most par­tic­i­pants bring solo kayaks, with and with­out sail and outrig­ger sup­port. Cov­er­ing this 300-mile course in a kayak within the eight-day time limit, how­ever, is a se­ri­ous en­deavor, and fin­ish­ers are the ex­tremely fit and ca­pa­ble sort.

Pel­i­can Re­sort in Key Largo is the fi­nal des­ti­na­tion, and the win­dow to fin­ish of­fi­cially closes eight days af­ter the start. Ev­ery­one is re­quired to stop at three check­points along the way: From north to south, they’re Cape Haze Ma­rina, Chokolos­kee and Flamingo. Be­sides en­cour­ag­ing cour­ses in­side the coast­line’s bar­rier is­lands, the check­points are more con­ve­nient for kayak­ers than for sail­boats. Con­versely, rough-wa­ter stretches across Tampa Bay, Pine Is­land Sound and, po­ten­tially, the Gulf, fa­vor ro­bust sail­ing ves­sels. When us­ing a short portage in Flamingo, kayaks can even cross White Wa­ter Bay, thus ap­proach­ing Flamingo from the in­side. Pad­dlers fa­vor the 99- mile in­side track from Ev­er­glades City to Flamingo known as the Wilder­ness Wa­ter­way. Go­ing out­side, how­ever, is much more di­rect, and faster for sailors.

My ves­sel of choice for this chal­lenge is Kairos, a ca­pa­ble An­gus Rowcruiser. The boat, avail­able as a kit or set of plans, is ideal for ex­tended bouts of wa­ter camp­ing

and mixed cruis­ing/rac­ing oc­ca­sions. This race will also serve as prac­tice for my 2018 Race to Alaska, a sim­i­lar race that starts in Port Townsend, Wash­ing­ton, and fin­ishes in Ketchikan, Alaska. I re­tired from the 2017 R2AK when a mast sup­port bracket (of my own en­gi­neer­ing) in my new and untested boat came loose af­ter 150 miles. I’ve since sorted the is­sue out for the race, and I’m con­fi­dent the is­sue has been fixed. I also switched from a furl­ing main, scav­enged from a Ho­bie Is­lan­der, back to An­gus’ orig­i­nal de­sign with a fully bat­tened main pat­terned af­ter the O’pen Bic.

Fri­day, the day be­fore the start, is a busy day. All 100 or so com­peti­tors are re­quired to com­plete a check-in process, which starts with com­plet­ing li­a­bil­ity waivers and a PFD in­spec­tion be­fore mov­ing to boat and equip­ment checks. The in­spec­tions are thor­ough. I have to demon­strate that my emer­gency knife, tied to my PFD, can be opened us­ing one hand. Check. My Garmin in­reach (a satel­lite-based emer­gency com­mu­ni­ca­tor and lo­ca­tor de­vice) must be tied to my PFD. Wear­ing the de­vice around my neck, over my dry­suit and un­der my PFD, is not ac­cept­able. Oh well. The knife, too, must be lashed to my PFD, not to my dry­suit pocket.

There’s an or­ga­ni­za­tional de­bate about whether my in­reach unit even qual­i­fies as the re­quired per­sonal lo­ca­tor bea­con. Opin­ions among the Water­tribe au­thor­i­ties dif­fer, but they even­tu­ally ac­cept the in­reach unit. My boat also needs to be equipped with a sep­a­rate Spot de­vice since that is the only type of satel­lite bea­con the of­fi­cial event web­site is able to track. I have one. It’s ac­ti­vated, it’s synced and it’s track­ing, so we are good.

I’ve al­ready been sail­ing Kairos for the past two days in prepa­ra­tion, so I bring my as­sem­bled boat around from the Fort de Soto boat ramp to East Beach, from which the race will start early next morn­ing. Race of­fi­cials, rec­og­niz­able by their clip­boards and match­ing T-shirts, pep­per me with ques­tions. “What kind of boat is this any­way?” “It’s an An­gus Rowcruiser.”

“Who built it?” “I did.” “Are these your reg­u­lar sails?” “Yes.” “How do you reef them?”

“Easy,” I ex­plain. “I en­gage the au­topi­lot (‘Wait. What? Your boat has an au­topi­lot?’ ), pull out the mast, re­move the sleeved sail and put the bare pole back into the mast step. I roll and stow the sail, get out a smaller

sail, put it on the mast, and off we go.” “No, I mean how do you reef the sails?” one of the in­spec­tors per­sists. “I just told you.” “But that’s not a proper reef­ing sys­tem.”

The back- and- forth con­tin­ues un­til he asks me if I can mod­ify my boat quickly.

“No, I don’t think I could or would want to,” I tell him. “And by the way, I have al­ready crossed the Strait of Juan de Fuca with this boat, in a gale, and Colin An­gus has com­pleted the en­tire R2AK in the same. You can look it up. It’s not an un­proven boat or rig­ging sys­tem.”

He doesn’t budge. Nor do I. “OK then,” he in­forms me, “you’re dis­qual­i­fied.” There’s no ques­tion I will sail the course re­gard­less of my sta­tus. I’m here for the sail­ing, to en­joy my time in the warm Florida wa­ters and na­ture, to en­joy sea­man­ship chal­lenges and em­brace the ca­ma­raderie of my fel­low sailors. Screw the rac­ing; that’s the least of it at this stage of my sail­ing life. I load the last sup­plies into the boat and dou­ble-check ev­ery­thing. I’m done by 7 p.m., and I head to town for one last full meal.

With a two- hour de­lay due to strong winds, the race fi­nally gets un­der­way from Fort de Soto on Satur­day morn­ing, March 3. Over the next two days we’ll move swiftly down the coast, pushed by a strong north­west­erly tail­wind and reel­ing in most of the 150 miles to Marco Is­land. Aside from

cut­ting out sleep, I don’t think there’s a way I can progress much faster. I ex­pect lighter winds ahead, and be­fore long, the re­lent­less pace slows to a crawl, giv­ing me a chance to cruise and en­joy these very unique wa­ters.

I reach the sec­ond check­point in Chokolos­kee af­ter dark on the third day. I an­chor close to the shore­line and ex­pe­ri­ence a sur­pris­ingly noisy night. Nearby Ev­er­glades City and its air­port are a ma­jor hub of con­struc­tion. Hur­ri­cane re­pairs, I guess.

Light winds per­sist the fol­low­ing morn­ing, di­rectly on the nose, so my progress is slow, and the an­noy­ances of wa­ter­front civ­i­liza­tion are grat­ing on me: high-rise con­dos, jet skis, power­boats, noise, traf­fic. I can’t wait to get away from it.

The fore­cast for the fol­low­ing day has the wind fresh­en­ing and shift­ing to the west, which gives me rea­son to dive into Lost­mans River at 2 p.m. I an­chor in a shal­low la­goon, away from the deeper chan­nel. I’m well pro­tected be­tween is­lands, but not so close that the no-see-ums are get­ting to me. Now I’m re­ally in­side the Ev­er­glades Na­tional Park, in a part called the Ten Thou­sand Is­lands, a vast and re­mote labyrinth of wa­ter and man­groves burst­ing with aquatic wildlife of all kinds, and a nurs­ery for many species.

I spend the late af­ter­noon tend­ing to the boat’s needs, read­ing and re­cov­er­ing from the pre­vi­ous day’s boat traf­fic. My choice of nav­i­ga­tion equip­ment is start­ing to break down, so that’s a ma­jor. I’m run­ning Navion­ics on a ded­i­cated iphone, with an­other one avail­able as backup. All de­vices are in water­proof hous­ings, and I have all the nec­es­sary power re­quire­ments to run the nav­i­ga­tional soft­ware: a so­lar panel and charged backup bat­ter­ies. What I had not an­tic­i­pated was the two charg­ing ca­bles quickly cor­rod­ing. Per­haps iphone tech­nol­ogy is not meant for the salty high seas af­ter all. I have pa­per charts, and this part of the coast is not dif­fi­cult to nav­i­gate, but now I bet­ter con­serve what­ever charges I have re­main­ing. I turn all phones off, and am left with satel­lite tracker and VHF ra­dio. There is no cell­phone cov­er­age here any­way, so I drift into a state of dis­con­nected bliss.

As the evening light fades, life in this un­spoiled bay is trans­for­ma­tive. I hear the man­groves come alive. There’s splash­ing in the chan­nel, fol­lowed by four deep breaths, which means dol­phins are round­ing up mul­lets. My mizzen sail, now point­ing for­ward, is let­ting me know that the out­go­ing tide has placed me gen­tly onto the sandy ground. I might not have no­ticed it oth­er­wise, such is the sta­bil­ity of my lit­tle tri­maran. This night shall be the only one of the en­tire trip dur­ing which I’m not hear­ing a com­bus­tion en­gine.

By morn­ing, the wind shifts south­west and strength­ens. I ven­ture out into the Gulf, tack­ing oc­ca­sion­ally. The waves of the shal­low coast slow my progress. By af­ter­noon, I’m well past Lit­tle Shark River, the last pro­tected an­chor­age be­fore I have to com­mit to round­ing Cape Sable, from which I can head for the next check­point in Flamingo. Dark thun­der­clouds bil­low to the west and move closer. I swear I can see wa­ter­spouts. Time to reef my main­sail. The gust bands miss me by a mile or so, and soon I’m back to the full main. It’s get­ting late. If I con­tinue beat­ing around Cape Sable, I’ll be ap­proach­ing Flamingo in the dark. With pa­per charts only, and no need to rush, I back­track into the an­chor­age in­side Lit­tle Shark River. This con­cludes an­other mel­low cruis­ing day, fol­lowed by an­other af­ter­noon of soli­tude, read­ing and ob­serv­ing. As dusk falls, Venus is vis­i­ble first. The night sky, away from light pol­lu­tion, is truly mag­nif­i­cent.

Thurs­day morn­ing, I make way for Flamingo again. A steady 15-knot west­erly kicks up brown chop, which makes for good sail­ing con­di­tions and a de­ci­sively wet pas­sage around Cape Sable. I ar­rive at the Flamingo check­point by 2 p.m., where I’m in­formed by race of­fi­cials that the sole stand-up pad­dle­board par­tic­i­pant had died a few days ear­lier when he fell off his board and drowned. I also learn that Smyth cap­sized dur­ing the first night and was res­cued by the Coast Guard.

A friend is wait­ing for me in Flamingo. She’s fol­lowed my tracker and greets me with my car and boat trailer. Since I’m not an of­fi­cial en­trant, I re­trieve my backup charg­ing ca­bles from the car, thus re­gain­ing full dig­i­tal nav­i­ga­tion but tech­ni­cally vi­o­lat­ing the no-out­side-sup­port rule. I could promptly head out again and cross Florida Bay in the fa­vor­able west wind, but I’m in cruis­ing mode now and opt for deeper ex­plo­ration of Flamingo and a hot shower at the camp­site. It’s cool and windy, so the in­fa­mous Flamingo mos­qui­toes are kept at bay.

The fol­low­ing morn­ing, I leave early to sprint to the Keys. I choose a route that takes me south and then east to­ward Key Largo. There is a more di­rect route, as the pel­i­can flies, but with a fore­cast of in­creas­ing head­winds, I don’t like that al­ter­na­tive.

Once out of Flamingo’s chan­nel, I em­ploy a neat lit­tle trick I’ve learned Kairos can per­form. With the dag­ger­board all the way up and my cas­sette rud­der blade ex­tend­ing only as deep as the skeg of the main hull it­self, I’m able to steer a con­trolled track down­wind over mud flats as shal­low as 10 inches. When the wind gets soft, I row a lit­tle.

The af­ter­noon wind re­mains light, and I barely com­plete the cross­ing be­fore dark, spend­ing my fi­nal night on the course tied to a wrecked dock on Up­per Mate­cumbe Key. There’s a bar on the other side of the noisy road, and at 4 a.m., po­lice of­fi­cers knock on my boat and ask that I move, cit­ing li­a­bil­ity rea­sons. I de­ploy my an­chor 50 feet far­ther up this lit­tle creek and wait for sun­rise.

A few hours later, a fresh southerly pro­vides su­perb sail­ing con­di­tions over flat wa­ter. A quick 25-mile dash and I’m cross­ing the fin­ish on Key Largo by noon, re­laxed, cruised and with­out a sin­gle blis­ter. With one last com­peti­tor ex­pected to ar­rive af­ter me, the dropout rate will be less than 20 per­cent. At 5 p.m., the of­fi­cial post-race party starts at the lo­cal kayak out­fit­ters shop, with beer, sushi and an im­promptu me­mo­rial ser­vice for the de­ceased pad­dler.

While the Ev­er­glades Chal­lenge is com­plete, for me at least, my mind and body crave the care­free rhythm of the pre­vi­ous days. I head out again the fol­low­ing morn­ing, my bows point­ing south to dis­tant keys. The ad­ven­ture con­tin­ues. Q



An­chored south of Cape Haze, the au­thor boils wa­ter for a break­fast of hot ce­real and tea. Kairos’ gale-strength main­sail is just big enough to bal­ance the mizzen and as­sist tack­ing. In the In­tra­coastal Wa­ter­way near Venice, Florida, Kairos paces a...

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