Spe­cial Re­port

Cruising World - - Contents - Elaine Lembo is a CW ed­i­tor at large.

Ef­fort­less broad reach­ing, a dip in re­fresh­ing waters, cock­tails in the cock­pit, re­unions with fam­ily and friends, a chance to learn a new on­board skill — those are the rea­sons va­ca­tion sailors say they re­turn year af­ter year to their bare­boat com­pany of choice.

But why do the own­ers and op­er­a­tors of these com­pa­nies do it? Aside from the ob­vi­ous rea­son — it’s a way to earn a liv­ing — run­ning a charter com­pany isn’t magic. It’s work. Or, “a la­bor of love,” as one put it.

A roundup of a dozen suc­cess­ful small bare­boat charter com­pa­nies, some of them fam­ily-owned and in busi­ness for decades, re­veals why they got in and how they stay in the game. Com­pa­nies also ex­plain how their ap­proach helps them shape and pri­or­i­tize their busi­ness goals, and what the chal­lenges are, as well as the op­por­tu­ni­ties — from op­er­at­ing in the vir­tual sphere of dig­i­tal tech­nol­ogy to mind­ing the fleet in the flesh by walk­ing the docks and send­ing sailors out in divergent, if gor­geous, cruis­ing grounds.

Ori­gins/mo­tives/ge­n­e­sis Fresh from ca­reers in ho­tel man­age­ment and bank­ing, Cindy Ch­est­nut and Brian Gandey knew what they sought when they started Conch Char­ters at Fort Burt Ma­rina on the is­land of Tor­tola, in the Bri­tish Vir­gin Is­lands, in 1987.

“We al­ways wanted to be a small com­pany,” Ch­est­nut says. “And it was also a con­scious choice to lo­cate Conch Char­ters at a sailor’s ma­rina rather than a fancy ma­rina. We went for a lo­ca­tion that al­lowed us to pass the sav­ings on to our cus­tomers. And our cus­tomers seem to ap­pre­ci­ate that more than hav­ing a swim­ming pool.”

What Gandey and Ch­est­nut car­ried out, par­lay­ing skills learned in one in­dus­try to do well in an­other, also worked for oth­ers.

Me­rion and Jen­nifer Martin run a mixed fleet of 25 power- and sail­boats

A roundup of a dozen suc­cess­ful small bare­boat charter com­pa­nies, some of them fam­ily-owned and in busi­ness for decades, re­veals why they got in and how they stay in the game. BY ELAINE LEMBO

at Des­o­la­tion Sound Yacht Char­ters in Co­mox, Bri­tish Columbia, Canada. “Hav­ing worked in the su­pery­acht in­dus­try in Europe and the Caribbean charter cir­cuit for years has given us the ex­pe­ri­ence to know what peo­ple ex­pect and how to ex­ceed their ex­pec­ta­tions,” Jen­nifer says.

Dave Con­rad, of Great Lakes Sail­ing Co. in Tra­verse City, Michi­gan, says he and his wife, Kris­ten, met while he was man­ag­ing a charter base in the Caribbean. To­gether, the cou­ple worked aboard crewed yachts be­fore buy­ing the Tra­verse City 20-strong fleet of sail- and power­boats.

“Our suc­cess is a di­rect re­sult of our hands-on ap­proach to run­ning the com­pany,” Con­rad says. “In the early days, we had lit­tle to no staff. We com­mis­sioned over 20 boats ev­ery year. We painted ev­ery bot­tom, did all the rig­ging, re­pairs and main­te­nance, and an­swered ev­ery phone call our­selves. We worked boat shows to­gether even when Kris­ten was eight months preg­nant.”

Some sailors got into the busi­ness so they could im­merse them­selves in a beloved pas­time. “We started 40 years ago with one boat, as a way to help pay for it,” says Roger Van Dyken, of San Juan Sail­ing in Belling­ham, Wash­ing­ton. “It turned into a hobby, then a plea­sur­able ac­tiv­ity, and then, when we formed the busi­ness, it be­came an en­joy­able en­ter­prise.”

As Patti Gon­salves, of Cruise Abaco in the Ba­hamas, puts it, “We started the com­pany with our own per­sonal boat, grew to three, and just kept grow­ing.”

For Brian Blank, of New­port, Rhode Is­land, this “la­bor of love” arose from a brush with Amer­ica’s Cup fame. “I was work­ing a sum­mer job in 1977 at Ban­nis­ter’s Wharf and be­came part of the dock crew for Ted Turner and Coura­geous,” Blank re­calls. “Most fun I’ve ever had! I guess I just fell into the boat­ing lifestyle and ad­ven­tures. I ended up buy­ing my first 38-foot sail­boat for charter in 1985 and have never looked back!” His Bare­boat Sail­ing Char­ters 15-mem­ber fleet floats on moor­ings in Bren­ton Cove, in New­port Har­bor. Know Your Niche, and Set Pri­or­i­ties Serendip­ity didn’t play a ma­jor role in Kurt Jer­man’s busi­ness plans when he opened the charter por­tion of West Coast Mul­ti­hulls in 2011 in San Diego, but un­der­stand­ing the mar­ket did.

“There have al­ways been plenty of schools and charter lo­ca­tions in the South­east­ern United States, the Ba­hamas and the Caribbean,” he says. “The key for us has been to fill a void in the mar­ket here on the West Coast with cata­ma­ran in­struc­tion and char­ters.”

A few lo­cal sail­ing clubs dab­bled in cata­ma­rans, Jer­man says, “but none re­ally knew that much about the boats, or the cata­ma­ran busi­ness as a whole. As a re­tail out­let for mul­ti­ple cata­ma­ran man­u­fac­tur­ers, my com­pany had been im­port­ing cats to the West Coast since 1999.”

With an em­pha­sis on teach­ing and cer­ti­fy­ing as­pir­ing cat sailors, the busi­ness has gone from a two-boat, one-base cen­ter to a 10-boat, two-base con­cern, with a fleet of 10 pri­vately owned cats from 35 to 58 feet in length. The new base, opened in high sea­son 2018, is at Puerto Es­con­dido, in the city of Loreto, Baja Cal­i­for­nia Sur, Mex­ico, off the Sea of Cortez.

If charter is the “try be­fore you buy” gate­way to in­formed own­er­ship, West Coast Mul­ti­hulls has a fra­ter­nal East Coast twin. Over 25 years in ex­is­tence, Maine Cat, of Bre­men, Maine, has built 140 of its fast, light sail and power cata­ma­ran mod­els in a range of lengths to an en­thu­si­as­tic clien­tele. Its fo­cus is on boat­build­ing and di­rect sales to cus­tomers.

“When peo­ple say, ‘Let’s go charter a boat,’ Maine Cat is not the first com­pany that comes to mind,” says owner Dick Ver­meulen. “If you want to go sail­ing, we’re not the typ­i­cal charter boat — our cats are per­for­mance cruis­ers.

“Our fo­cus is not chartering. Hav­ing said that, our base in the Ba­hamas al­lows peo­ple to try one of our mod­els and see if they like it.” The com­pany’s base in Abaco, Ba­hamas, and its one-cat charter avail­abil­ity from Rock­land, Maine, are live show­rooms, and typ­i­cally fully booked.

While charter is a valid means for sailors and as­pir­ing sailors to tran­si­tion to own­er­ship, the crit­i­cal stage of in­struc­tion can’t be over­looked, and that too has long been an in­gre­di­ent of the recipe for suc­cess for West Coast Mul­ti­hulls, Maine Cat and count­less other charter out­fits. Schools of­fer cer­ti­fi­ca­tion through cus­tom cur­ricu­lums or through or­ga­ni­za­tions such as the Amer­i­can Sail­ing As­so­ci­a­tion and US Sail­ing.

“We have been an ASA school since 1985 — one of the old­est still around,” says Barb Hansen, of South­west Florida Yachts. “We see even more of a need for in­struc­tion now as the baby boomers get close to re­tire­ment. They now have the means to buy a boat, but might not have the skills.”

And Hansen, faced with count­less as­pir­ing own­ers, feels ob­li­gated to as­sess their needs. “When peo­ple come and ask me to help them find a boat to buy, I ask them what their ex­pe­ri­ence is,” she says. “If they have none, I strongly sug­gest they go through our classes first. I tell them, ‘I would be happy to sell you a boat, but you would be buy­ing a boat with­out the proper knowl­edge or ex­pe­ri­ence.’ As with any­thing else, an in­formed buyer is go­ing to be a bet­ter owner.”

Other com­pa­nies, such as South Coast Sail­ing Ad­ven­tures in Kemah, Texas, near Galve­ston Bay, re­main ded­i­cated and fo­cused on in­struc­tion. “Our sail­ing school is the core of our busi­ness,” says owner Lucy New­man. “We strive to train com­pe­tent and knowl­edge­able sailors, with a fo­cus on safety and cour­tesy, while still hav­ing fun. We strongly be­lieve that safe boat­ing is achieved through ed­u­ca­tion.”

With a view to longevity, Cindy Kalow, of Su­pe­rior Char­ters in Bay­field, Wis­con­sin, adds, “In­struc­tion is now para­mount to our abil­ity to main­tain a fresh cus­tomer base and cre­ate fu­ture sailors. We would not still be in busi­ness if we didn’t have a train­ing/cer­ti­fi­ca­tion arm to our busi­ness.”

Chal­lenges and Op­por­tu­ni­ties

Fleet ma­tu­rity is a chal­lenge that some smaller charter com­pa­nies have had to deal with, and some have had an un­prece­dented hur­ri­cane sea­son trans­form their busi­ness plan.

“The im­age of us hav­ing older boats is one we’ve been work­ing hard to al­ter; our old­est boats are now 7 or 8 years old,” says Ch­est­nut, of Conch Char­ters, of a fleet that grew to 56 a few years back. “Of course, hur­ri­canes Irma and Maria in

Septem­ber 2017 af­fected that.”

As Conch ral­lied to get un­der way in time for char­ters in high sea­son 2018 with a dozen boats, Ch­est­nut says, “We never an­tic­i­pated that we’d be at this junc­ture at this point. We want to con­tinue to re­build — it’s Conch Char­ters. It’s our baby. We don’t want to see it go poof! We’re com­ing back.”

Mother Na­ture isn’t the only force at play. “The mar­ket has changed,” says Kalow. “Peo­ple no longer par­tic­i­pate in just a few hob­bies or ac­tiv­i­ties. In the past, peo­ple would la­bel them­selves a sailor or a golfer. Our younger cus­tomer base is very ac­tive and has a lot of in­ter­ests. We con­tin­u­ally work to tap into new mar­kets and cus­tomers who are look­ing for new and dif­fer­ent ex­pe­ri­ences. You have to keep your prod­uct fresh, un­der­stand what you of­fer and stay sharp on how you present that of­fer­ing.” Then there’s the ef­fort you put out. “We have worked our tails off for nearly 35 years,” says Hansen. “I’m still here seven days (and nights) a week, with the oc­ca­sional day off. If you don’t have that pas­sion for your busi­ness, then you won’t suc­ceed. You have to be­lieve in what you do and then try to do the best job you can do.”

Rapid ad­vances in dig­i­tal tech­nol­ogy have also had a ma­jor im­pact, and present new pos­si­bil­i­ties. “The shar­ing econ­omy has opened up peo­ple’s eyes to unique lodging op­por­tu­ni­ties, and be­ing based in San Diego makes it easy for us to of­fer Cruise-n-snooze charter stays on the boat, like Airbnb on the wa­ter with a sun­set cruise thrown in,” Jer­man says. “That might have been hard to ex­plain be­fore, but now peo­ple just get it.”

Adds Ch­est­nut, “Peo­ple are more eas­ily reached and found. Our reser­va­tion sys­tem is on­line. We put an e-tablet on each boat with the chart brief­ing and all charts and a nav sys­tem, as well as fun facts like plants and fish they might en­counter. We have a check­list of each yacht’s sys­tems. If char­ter­ers have a prob­lem while they’re out, they can take a pic­ture and send it to us via a text or email.”

It’s Magic — or Is It?

Com­pany own­ers en­joy de­scrib­ing the in­ef­fa­ble twist to at­tract­ing re­peat clien­tele.

“We re­trieve lost lug­gage and de­liver it, grab the bag of ice they for­got, pick up their trash on the wa­ter if they missed the drop-off in a set­tle­ment,” says Gon­salves, of Cruise Abaco. “When the owner of the com­pany is the one who you see on the dock and on the wa­ter, you know you’re be­ing taken care of. No re­quest is im­pos­si­ble!”

“We make sure the client gets what he or she paid for — a fan­tas­tic time on the wa­ter,” Jer­man says. “There’s a risk in mak­ing things over­com­pli­cated.”

Re­silience in the face of set­backs such as hur­ri­canes also scores big with sailors. “At the end of the day, it’s all about at­ten­tion to de­tail and giv­ing peo­ple a lit­tle bit more than they ex­pect — a beach bag, a bot­tle of rum,” says Ch­est­nut. “One client has been chartering with us for 27 years for two weeks a year. They ask us if they can bring any­thing down. They’ve brought us starter mo­tors for cars, maple syrup. That’s what makes our com­pany nice. It’s like a fam­ily.”

It helps that, by and large, a charter trip is a happy ex­pe­ri­ence. “Our cus­tomers are on va­ca­tion!” Hansen says. “It’s not like they are go­ing in for a root canal. We love that we are of­ten ful­fill­ing a dream for some­one or we are help­ing them plan the trip of a life­time!”

It works at San Juan Sail­ing too. “Our staff de­rives sheer joy from help­ing peo­ple have joy — pe­riod,” Van Dyken says. “Noth­ing beats pas­sion­ate, self­less ser­vice.”

Blank, of Bare­boat Sail­ing, sticks to this phi­los­o­phy: “Keep your cus­tomers happy, and they will al­ways come back.”

I roll off the cock­pit set­tee, pop my head over the dodger and look into the night. Twenty de­grees off our star­board bow, I do see it: three white lights in a ver­ti­cal line, then a red light be­low and to the left of the oth­ers. “I’ve been watch­ing him for a while,” Hank says. “His bear­ing hasn’t changed.” My first re­ac­tion is to call for an ex­ag­ger­ated turn to port. As I try to shake off sleep, an exam ques­tion flick­ers from some dim re­cess.

You are ap­proach­ing an­other ves­sel at night. You can see both red and green side­lights and, above the level of the side­lights, three white lights in a ver­ti­cal line. The ves­sel may be ___________ . a. not un­der com­mand b. tow­ing a tow more than 200 me­ters astern c. trawl­ing d. un­der­way and dredg­ing

My heart races be­fore I call for the course change; an­other ques­tion runs through my mind.

You are aboard the give-way ves­sel in a cross­ing sit­u­a­tion. Which of the fol­low­ing should you NOT do in obey­ing the Nav­i­ga­tion Rules? a. cross ahead of the stand-on ves­sel b. make a large course change to star­board c. slow your ves­sel d. back your ves­sel Adren­a­line wal­lops me. “Turn 90 de­grees to star­board,” I say. For the next minute or so, the tug moves safely across our port side, and soon we both see the faint red side­light of its barge some hun­dreds of yards be­hind. I think of the hawser con­nect­ing them, lethal and in­vis­i­ble, then sit chat­ting with Hank for a few min­utes be­fore ly­ing back down for an­other 20-minute nap. (For the record, the cor­rect an­swers are B and A.)


I’ve joined Shawn Brown and Hank Sch­midt as their in­struc­tor for a pair of cour­ses — Coastal Nav­i­ga­tion and Coastal Pas­sage Mak­ing — two in­ter­me­di­ate steps in a tiered cur­ricu­lum from novice to ex­pert that’s cre­ated and ad­min­is­tered by the United States Sail­ing As­so­ci­a­tion, or US Sail­ing (us­sail­ing.org). Shawn is an air­plane pi­lot who’s re­cently left a tech startup and is now look­ing to buy a 50-some­thing-foot ketch to live and cruise aboard. Hank (no re­la­tion to the Hank Sch­mitt who or­ga­nizes cruis­ing ral­lies un­der the Off­shore Pas­sage Op­por­tu­ni­ties name) is a New York City emer­gency-room physi­cian who hopes to start crew­ing on ocean-sail­ing trips from the U.S. East Coast to the Caribbean. Both would like to charter sail­boats in dif­fer­ent places around the world. If they can suc­cess­fully per­form the hands-on tasks laid out in each course and pass the writ­ten ex­ams, they’ll re­ceive US Sail­ing cer­tifi­cates that demon­strate to charter com­pa­nies and skip­pers that they’ve at­tained a rig­or­ous level of pro­fi­ciency in these dis­ci­plines.

For this trip, we’re sail­ing Matilda,a newish Hanse 505 man­aged by New Eng­land Sail­ing Cen­ter in New­port, Rhode Is­land. The Coastal Pas­sage Mak­ing cur­ricu­lum in­cludes night pas­sages, so we plot a track that will take us from Nar­ra­gansett Bay out to Shel­ter Is­land at the east­ern end of Long Is­land, then across Block Is­land Sound to Martha’s Vine­yard, be­fore re­turn­ing to New­port — a tri­an­gle of some 200 miles over five days, in­clud­ing two overnighters.

Af­ter stow­ing pro­vi­sions and get­ting fa­mil­iar with the boat’s sys­tems, we work through this ques­tion to­gether:

The Hanse 505 is fit­ted with a Volvo D2 diesel en­gine and 75 gal­lons of fuel. If she cruises at 6.5 knots and burns 1.75 gal­lons per hour at 2,200 rpm, what is Matilda’s safe cruis­ing range un­der power? a. 75 miles b. 175 miles c. 275 miles d. 375 miles It takes two steps to an­swer the ques­tion. We know that the en­gine burns 1.75 gal­lons per hour and that Matilda will travel a dis­tance of 6.5 miles in one hour. Our first step is to fig­ure out how far we’ll travel on a gal­lon of fuel. Di­vid­ing 6.5 miles by 1.75 gal­lons gives the an­swer: 3.71 miles per gal­lon.

Next, we need to know how far our tank of fuel will carry us. Mul­ti­ply­ing 75 gal­lons by 3.71 miles per gal­lon gives a re­sult of 278 miles. An­swer C, 275 miles, is math­e­mat­i­cally pos­si­ble but not a safe cruis­ing range. Ap­ply­ing a safety fac­tor of 25 per­cent leaves us with a range of 208 miles. The an­swer B, 175 miles, leaves us a safety fac­tor closer to a third of a tank. B is the best an­swer to this ques­tion. In prac­ti­cal terms, this means that even if the wind shuts off all week, we could still com­plete our itin­er­ary with­out re­fu­el­ing.

We spend our first af­ter­noon sail­ing in Nar­ra­gansett Bay, cal­cu­lat­ing time-speed­dis­tance prob­lems and plot­ting courseto-steer vec­tors through the tidal cur­rent as we reach over the top of Co­nan­i­cut Is­land, then tack down the West Pas­sage to Dutch Har­bor. Shawn and Hank study the chart and se­lect a spot near the mouth of Great Creek that shows 14 feet of depth at mean low wa­ter and is marked with an “M” for its mud bot­tom. Cal­cu­lat­ing for 7-to-1 scope and tak­ing into ac­count the tidal range and our 5 feet of free­board, they set the hook, then put out 160 feet of rode. We grill chicken, share a few laughs and turn in early.

Our trip’s first night pas­sage be­gins at 0200.


US Sail­ing, which has ex­isted in one form or an­other for more than 120 years, de­scribes it­self as “the na­tional gov­ern­ing body for the sport of sail­ing.” In the 1980s, it got into the busi­ness of teach­ing sail­ing, with an ini­tial fo­cus on kids and small boats. In the 1990s, it be­gan de­vel­op­ing cour­ses for adult sailors in big­ger boats — “keel­boats,” as op­posed to dinghies, and cruis­ing in ad­di­tion to

rac­ing. Sim­i­lar in­struc­tional pro­grams are avail­able that lead to Amer­i­can Sail­ing As­so­ci­a­tion cer­ti­fi­ca­tion (see “ASA Cour­ses and Cer­ti­fi­ca­tions,” page 40).

Two years ago, US Sail­ing re­or­ga­nized it­self to sim­plify its sev­eral mis­sions. Now there’s a ded­i­cated Youth depart­ment, which fo­cuses on teach­ing kids to sail small boats through lo­cal sail­ing schools, yacht clubs and com­mu­nity sail­ing cen­ters. Its Youth net­work in­cludes some 1,500 in­struc­tors. Other US Sail­ing de­part­ments sup­port sail­boat rac­ing up to the Olympic level, pro­vid­ing rules, coach­ing, mea­sure­ments and other tools to cre­ate a level com­pet­i­tive play­ing field.

The cour­ses Shawn and Hank are tak­ing fall un­der US Sail­ing’s Adult depart­ment. Since Jan­uary 2017, that di­vi­sion has been led by Betsy Ali­son, a cham­pion in sev­eral senses of the word. Five-time win­ner of the Women’s Keel­boat Cham­pi­onships, five-time Rolex Yachtswoman of the Year and 2011 Na­tional Sail­ing Hall of Fame in­ductee, her com­pet­i­tive record speaks for it­self. But in a broader sense, Betsy has long

been a cham­pion of pro­vid­ing peo­ple ac­cess to the wa­ter, espe­cially folks with clear bar­ri­ers. In 2015, she won the ISAF World Sail­ing Pres­i­dent’s De­vel­op­ment Award for her work as head coach of the US Par­a­lympic Sail­ing Pro­gram.

In her new role, Betsy’s mis­sion has broad­ened. “We just want to get butts in boats,” she told me last win­ter. “We want peo­ple to try sail­ing and have a hands-on ex­pe­ri­en­tial learn­ing op­por­tu­nity that hope­fully sparks their in­ter­est and makes them want to con­tinue.”

For Betsy and her depart­ment, that mis­sion starts with a pro­gram called First Sail (us­sail­ing.org/ed­u­ca­tion/adult/first­sail). First Sail ses­sions typ­i­cally run two hours and cost be­tween $35 and $100 per per­son; af­ter that, many clubs or schools of­fer dis­counts on fu­ture lessons. “We have First Sail lo­ca­tions that are not US Sail­ing keel­boat schools or yacht clubs,” Betsy said. “And we don’t mind whether some­one is us­ing ASA in­struc­tors or vol­un­teer in­struc­tors or what­not. It’s the first en­try point in my depart­ment, and it’s for peo­ple who have never tried sail­ing be­fore.”

The next step for folks who want to learn more is US Sail­ing’s Adult Keel­boat pro­gram — and this is the track Shawn and Hank are fol­low­ing. The US Sail­ing web­site in­cludes a list of ac­cred­ited schools that of­fer cer­ti­fi­ca­tion (us­sail­ing .org/ed­u­ca­tion/adult/cer­ti­fi­ca­tion-cours­esendorse­ments/find-a-school). With about 75 schools on the list, that net­work is smaller than what you’ll find with US Sail­ing’s Youth pro­gram (1,500 in­struc­tors) or the Amer­i­can Sail­ing As­so­ci­a­tion (roughly 300 schools and clubs).

The Adult Cruis­ing Track lays out a pro­gres­sive set of stan­dard­ized step­ping stones to lead novices to­ward sail­ing ex­per­tise: Ba­sic Keel­boat Ba­sic Cruis­ing Bare­boat Cruis­ing Cruis­ing Cata­ma­ran En­dorse­ment Coastal Nav­i­ga­tion Coastal Pas­sage Mak­ing Ce­les­tial Nav­i­ga­tion Off­shore Pas­sage Mak­ing In ad­di­tion to these, US Sail­ing of­fers other tar­geted pro­grams, in­clud­ing Safety at Sea cour­ses and a host of on­line in­struc­tion. “If you look at the mil­len­nial gen­er­a­tion,” Betsy said, “they don’t want to own things. They want to go to a com­mu­nity sail­ing pro­gram or to a shared­boat club and lease or charter a boat and en­joy it with­out hav­ing to make the big fi­nan­cial in­vest­ment in it. So this year we’ve started ex­pand­ing our small keel­boat pro­gram.” For such peo­ple, cer­ti­fi­ca­tions are their ticket to rent­ing boats. So, US Sail­ing ex­panded its pro­gram last year to in­clude Per­for­mance Keel­boat. “It’s an op­por­tu­nity to teach peo­ple to sail their boats bet­ter and faster with­out be­ing re­lated to rac­ing.” It’s also un­re­lated to the more sys­tems-heavy cruis­ing track.

An­other new course comes un­der the head­ing of US Power­boat­ing. “What sets us apart from some of the other power­boat-in­struc­tion providers is that our pro­grams are all fo­cused around hands-on, ex­pe­ri­en­tial learn­ing,” Betsy said. “So you learn how to pivot-turn; you learn how to dock and un­dock, and all the lit­tle nu­ances that you don’t get if you sit on­line for your boater’s ed­u­ca­tion card.”


The full re­al­ity of that hands-on, ex­pe­ri­en­tial in­struc­tion hits us at 0130, when wakeup alarms start ring­ing through Matilda’s cabin. Af­ter that ini­tial jolt, only the clat­ter of the an­chor chain breaks the mid­night si­lence as we hoist the main and sail off our an­chor en­gine­less. A gen­tle southerly and the ebbing cur­rent take us qui­etly out past the Dutch Har­bor moor­ing field and back to­ward West Pas­sage.

“See that red light that’s flash­ing twice then once ev­ery six sec­onds?” I say to Shawn. “Keep that just off our star­board bow.” This is the pre­ferred-chan­nel buoy “DI” at the south end of Dutch Is­land — red on top, green on the bot­tom, with a com­pos­ite group-flash light pat­tern at night. We talk about how boats trav­el­ing north up the West Pas­sage treat this nav­i­ga­tion aid as a red mark if they in­tend to con­tinue up the main chan­nel but as a green mark if they’re go­ing up the sec­ondary chan­nel into Dutch Har­bor. When Shawn and Hank take their exam at the end of the week, they’ll re­mem­ber this mo­ment; at least five ques­tions deal with aids to nav­i­ga­tion, and more than one of those asks about pre­ferred-chan­nel buoys.

With sun­rise off Point Ju­dith comes the New Eng­land fog — the “smoky sou’wester,” as ad­vec­tion fog is known in these parts, rec­og­niz­ing the strange pair­ing of zero vis­i­bil­ity with a rip­ping breeze. What should we do?

Shawn combs through the Nav­i­ga­tion Rules to find out. Sub­part D cov­ers “Sound and Light Sig­nals.” Rule 35 treats “Sound Sig­nals in Re­stricted Vis­i­bil­ity.” That’s us. “In or near an area of re­stricted vis­i­bil­ity, whether by day or night,” he reads, “a power-driven ves­sel mak­ing way through the wa­ter shall sound at in­ter­vals of not more than two min­utes, one pro­longed blast.” Else­where we read that a pro­longed

blast sounds for four to six sec­onds. Sure enough, we can hear one of those off our port beam — and it’s get­ting louder. But that sig­nal is for power-driven ves­sels, and we’re sail­ing with our en­gine off. What about us? “A ves­sel not un­der com­mand; a ves­sel re­stricted in her abil­ity to ma­neu­ver, whether un­der­way or at an­chor; a sail­ing ves­sel; a ves­sel en­gaged in fish­ing, whether un­der­way or at an­chor; and a ves­sel en­gaged in tow­ing or push­ing an­other ves­sel shall … sound at in­ter­vals of not more than two min­utes, three blasts in suc­ces­sion, namely, one pro­longed fol­lowed by two short blasts.” And so for the next three-quar­ters of an hour till the fog clears, we take turns blow­ing the air horn — one pro­longed, two short blasts, ev­ery two min­utes. The sound of the other boat moves aft, but we never catch sight of it.

Through the morn­ing and the early af­ter­noon, we de­vise a watch sched­ule to make up for last night’s short nap, and we set up a de­tailed log of our progress. All day we mo­tor sail a lit­tle south of west to­ward Gar­diners Point, keep­ing a close eye on the weather. The NOAA fore­cast calls for a pow­er­ful front ar­riv­ing later and bring­ing gale-force winds through the night. We call up Na­tional Oceanic and At­mo­spheric Ad­min­is­tra­tion’s graphic marine weather charts (nws.noaa.gov/om/marine/home .htm) and com­pare the sur­face anal­y­sis with the 12-, 24- and 48-hour fore­casts. We talk about the iso­bars, those lines of equal baro­met­ric pres­sure on the map, and how tighter iso­bars in­di­cate greater wind ve­loc­i­ties. We talk about the chang­ing sky, and what the progress from cir­rus to stra­tus to cu­mu­lus fore­tells. Later that night, safely an­chored in Shel­ter Is­land’s Coe­cles Har­bor, the shrieks through the rig­ging and the boat’s snappy pitch send home the mes­sage that what we’re learn­ing here isn’t just the­o­ret­i­cal.

The gale doesn’t quite blow it­self out till early af­ter­noon, so we use the next day for course­work at an­chor: tide prob­lems us­ing the rule of twelfths, set-and-drift plots, safety pro­ce­dures in cases of fire or crew over­board. We use the time to plot a cur­rent-cor­rected course back across Block Is­land Sound to Martha’s Vine­yard. Af­ter a swim and a late lunch, we up an­chor and set off in time to round Gar­diners Point by sun­set and be­gin our sec­ond overnight pas­sage.

By the time we re­turn to New­port af­ter five days out, the exam ques­tions for the Coastal Pas­sage Mak­ing cer­ti­fi­ca­tion seem a lit­tle less daunt­ing — and a lit­tle more real.

The greater the pres­sure dif­fer­ence be­tween a high- and low-pres­sure cen­ter, the: a. cooler the tem­per­a­ture will be b. drier the air mass will be c. warmer the tem­per­a­ture will be d. greater the force of the wind will be Fog formed by mois­ture-laden air mov­ing across a cold por­tion of Earth’s sur­face and con­dens­ing is called: a. sea fog b. ra­di­a­tion fog c. ad­vec­tion fog d. frontal fog A lighted pre­ferred-chan­nel buoy will show a: a. Morse (A) white light b. com­pos­ite group flash­ing light c. yel­low light d. fixed red light To pass the course and gain their


In ad­di­tion to the ex­cel­lent sail­ing schools you can find through the ASA or US Sail­ing net­works, you might also want to ex­plore some of the one-off cour­ses that of­fer guided sail­ing ex­pe­ri­ence but with­out stan­dard­ized cer­ti­fi­ca­tion.

Two oc­ca­sional CW au­thors, Teresa Carey and John Kretschmer, each run in­di­vid­u­al­ized off­shore sail-train­ing pro­grams, and there are plenty of oth­ers.

Carey and Ben Erik­sen lead Morse Al­pha Sail Train­ing (morseal­pha.com) aboard their Robert Perry-de­signed Norse­man 447. To­gether, they have 25 years of ex­pe­ri­ence in sail train­ing, wilder­ness medicine and Out­ward Bound ed­u­ca­tion. Both are U.S. Coast Guard-li­censed masters.

“The great thing about or­ga­ni­za­tions like ASA and US Sail­ing is that there are stan­dards of qual­ity and cur­ricu­lum on which stu­dents can rely,” Carey writes on her blog. “If you choose to go with an in­de­pen­dent or­ga­ni­za­tion like ours, you draw more of a wild card. You have to do your own re­search to know if you will be re­ceiv­ing qual­ity in­struc­tion from an ex­pe­ri­enced sailor.” What’s the case against cer­ti­fi­ca­tion? Ac­cord­ing to Carey, it’s the cost, the lim­it­ing cur­ricu­lum and the lack of ob­vi­ous ben­e­fits. “Each stu­dent makes progress at dif­fer­ent lev­els,” Carey says. “And not ev­ery­one fits well into a pre­de­ter­mined pro­gram. Ad­di­tion­ally, if a stu­dent’s abil­ity sur­passes the pre­scribed cur­ricu­lum, we are pre­pared to of­fer them a more chal­leng­ing ex­pe­di­tion.” Charter com­pa­nies and in­sur­ance providers, she ar­gues, care more about ex­pe­ri­ence than cer­ti­fi­ca­tion.

At press time, Kretschmer (yayablues.com) was lead­ing a group of stu­dents across the North At­lantic to the Azores. “When my sail­ing odome­ter ticked over 300,000 miles, I stopped count­ing,” Kretschmer wrote. His per­son­al­ized sail-train­ing pro­grams of­fer stu­dents a chance to glean some of that ex­pe­ri­ence.

“Our Off­shore Train­ing pas­sages are unique,” Kretschmer says. “And so are the peo­ple who find their way aboard. I am not a sail­ing school; there are plenty of those around, and many do a fine job of teach­ing off­shore sail­ing skills. What we do is dif­fer­ent. We make pas­sages; we make voy­ages. They’re real, some­times all too real. Each pas­sage is com­posed of crewmem­bers with vary­ing lev­els of ex­pe­ri­ence, and we learn from each other.”

A quick on­line search will turn up other in­di­vid­u­al­ized pro­grams — or “wild cards,” as Carey says. cer­ti­fi­ca­tion, Shawn and Hank need to an­swer at least 80 per­cent of these ques­tions cor­rectly (the an­swers to the ques­tions above are D, C and B, re­spec­tively). That’s 64 out of 80. But af­ter this week, all that the­ory from the text­book has been fleshed out with a boat­load of in­deli­ble mem­o­ries. All that said, this story has a happy end­ing: They passed.

CW ed­i­tor at large Tim Mur­phy holds a 100ton Mas­ter’s li­cense and has taught sail­ing for many years. He’s pre­par­ing a 1988 Pass­port 40, Billy Pil­grim, for long-dis­tance voy­ag­ing.

The San Juan Sail­ing fleet rafted up at the Oc­to­pus Is­lands marine park dur­ing a guided flotilla cruise of the San Juan and Gulf is­lands.

Maine Cat Char­ters (top) of­fers a great op­por­tu­nity not just for a va­ca­tion, but also for prospec­tive own­ers to try the boat out be­fore buy­ing. Brian Gandey and Cindy Ch­est­nut started Conch Char­ters in 1987.

West Coast Mul­ti­hulls hosts an an­nual fun rally to Catalina Is­land (above). Mark Gon­salves, owner of Cruise Abaco, smiles with cus­tomers (right). A Jean­neau from Des­o­la­tion Sound Yacht Char­ters rests in a pic­turesque an­chor­age.

Matilda’s crew (from top): air­line pi­lot Shawn Brown, in­struc­tor Tim Mur­phy and physi­cian Hank Sch­midt.

Af­ter our first good day of sail­ing, the hook was down in Dutch Har­bor off Co­nan­i­cut Is­land just in time for a mem­o­rable sun­set.

An­chored off Shel­ter Is­land, we waited for the gale (top). The fol­low­ing day was ideal for cock­pit course­work.

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