Mates of the Mac

Two complete strangers set off doublehanded in the Chicago YC’s Race to Mackinac seeking adventure and enlightenment.

Ahead, through bleary eyes, the lights of the Mackinac Bridge float on the horizon like a mirage. The twinkling blob is a distant target in the pitch-black night, the next waypoint on our 280-mile race from boisterous Chicago to sleepy Mackinac Island. All around us are blinking lights: reds, greens and whites of channel markers and the slower boats we’re creaming past at what sure feels like 15 knots. My co-skipper and I are sleep-deprived, hungry and thirsty for beer, and while we can’t yet smell the horse piss, we’re closing in on the finish at a wicked pace.

My concentration flicks between the bow, its angle to the waves, and the tightly curled luff of our bone-white masthead spinnaker. Standing so I can see better, my left foot is braced against the foot chock, tingling and numb. My right knee is bent, pressed against the side deck and the coaming, and my waist is wedged against the lifeline padding. When the load on the rudder lightens, I allow the tiller to glide away. The boat turns toward the wind, the luff flicks as the boat accelerates, and water jets across the foredeck.

The boat begins to surf, and the ­rudders howl like a banshee and then go quiet as froth tumbles out from the transom. A stronger gust tickles the hair on the back of my neck. I exhale deeply to calm my nerves and say to myself, Don’t wipe out…don’t wipe out…


My mate for this blitz through the Straits of Mackinac is Andraž Mihelin. He’s behind me, sitting wedged into the pushpit while navigating through a maze of markers using only his iPhone. He knows we’re pushing the boat and its runnerless carbon rig to a redline. This boat is his baby, and he knows better than anyone what will trigger a tantrum.

“Careful,” I hear him say to me. “You’re on the edge.”

Huh? On the edge?


I ponder that for a split second, afraid to ask what he means. Does my steering suck?

We’ve turned off the cockpit displays to save power, so I have no idea how fast we’re going or what direction the apparent wind is coming from, but it doesn’t matter. I’m sailing the 27-footer by feel, and I’m chuffed that I actually feel fully in control. The leeward rudder has a firm grip, and the boat, as the saying goes, feels as if it’s on rails. Tugging on the tiller keeps everything in balance.

With Chicago in the ­rearview mirror, the author and Andraž Mihelin tackle the Race to Mackinac, doublehanded and in the smallest boat of the fleet. Andraž Mihelin

“What do you mean by on the edge?” I ask him, without breaking my concentration on the bow.


“When there’s that much water coming across the deck, you’re on the edge,” he responds calmly. I hear what he’s saying, but I sure don’t feel as if I’m on the edge of anything, which is crazy because I’ve never driven a sportboat at such speed into the night—never mind with only two people and no one with a hand on the spinnaker sheet. If being on the edge means driving drunk on adrenaline and reckless confidence, well, bartender, give me another.

The finish line ahead of us is that of the 112th edition of Chicago Yacht Club’s Race to Mackinac, which is a big deal to the sailors of this giant freshwater playground. It’s the annual gem of the Great Lakes yachting calendar, a race that any Windy City sailor worth their weight in rum commits to every year—birth of a child or family ­wedding be damned.

The storied northbound race is not an easy test of skill and seamanship by any stretch, and that’s its appeal. There’s no one winning strategy (do you favor Wisconsin or Michigan this year?) and big weather comes fast and hard. Sometimes boats break or capsize, and the race is not without its fatalities. Its two- to three-day duration is just long enough to get knackered and feel as though you’ve accomplished something cool and a little bit dangerous, but it’s not too long as to leave you bored, sitting on the rail for days on end wishing you had a platter of piping hot chicken wings. There are quick ones and slow ones, and when it does come to a crawl, out come veracious lake flies, those nibbling nuances for which there is no known defense. They are the scourge of the race.


The fleet of this 2021 edition is smaller than some years past, but there are thousands of sailors itching to earn a new brag flag. This year’s scratch sheet runs the gamut, from an 86-footer to the grand-prix Great Lakes 52s, the ubiquitous Tartan 10s, and the two smallest boats of all: the Beneteau First 27SEs (Seascape Edition). I’m on one of them, racing in the doublehanded division against two 29-foot J/88s.

When I accepted an out-of-the-blue ­invitation to do the race with Mihelin, I did so without actually contemplating how small a 27-feet boat is relative to Lake Michigan. I also did not contemplate one important aspect of racing with only one other soul: Should one of us go overboard while the other is down below having a nap, the chance of survival is greatly reduced, especially when the water is cold. And this, I now understand, is why race organizers enforce the most comprehensive safety requirements of any race I’ve ever sailed. The must-have equipment for every boat is pages long, and every crewmember on every boat must be schooled in safety at sea.

Before the race, I had no safety qualifications, and I also neglected to disclose to Mihelin that I’d never once sailed a double­handed offshore distance race, nor doublehanded at night. I owned no safety equipment, except my PFD, and had not a single minute of safety training—online or in-person. Only after I complete my online classes do I realize how much I didn’t know, and while I should’ve been more at ease with my safety book smarts, the opposite happened: I got spooked with the thought of racing such a small and unknown craft on such a notorious stretch of water. With zero experience. With an unknown mate.

The mandatory equipment does get expensive, but I now own a top-shelf Mustang inflatable PFD and tether, an Ocean Signal AIS/DSC man-overboard ­beacon, an ACR personal EPIRB, a high-­quality headlamp, and a one-handed blunt-tip safety knife. Plus, I have a sample set of North Sails’ new top-shelf Gore-Tex foul-weather gear to keep me warm and dry. Having all the right gear, as the ­seminars preach, is half the battle.

Properly kitted, I feel more at ease when I arrive at the boat and assess its sea­worthiness for the first time. It could fit on the foredeck of Natalie J, the 52-footer next door. It’s definitely a sportboat built for two.

There are two other First 27SEs at the dock at Chicago’s Columbia YC. There’s a new one straight off a ship from the Seascape factory in Slovenia (which was supposed to be ours), one belonging to an owner from Texas who is relocating to the Great Lakes (we’re borrowing his), and the third is owned by local Mike Tuman, who prefers to solo his boat but is doing the race with Tit Plevnik from the Seascape team.

Mihelin is standing astride our little white boat, holding court. He’s only just arrived in Chicago, having conquered the US COVID‑19 foreign-entry maze. This is not Mihelin’s first Mac Race, though. In 2016, he won the doublehanded division with British solo sailor Phil Sharp and then raced with a crew of four in 2018. Both races were on the Seascape 27, as the First 27SE was called back in the days, an award-winning design from the boatbuilding company Mihelin founded in Slovenia with fellow sailor Kristian Hajnšek. Both gentlemen are disciples of Mini-class racing, having completed two Mini-Transat campaigns (from France to Brazil in crazy-fast 21-footers).

I will soon come to understand that Mihelin’s experiences from those ­intoxicating days of Mini racing define his character as well as his company. He preaches the tightknit community of Mini, the performance of Mini, and how Mini takes you light-years outside your comfort zone and then brings you back to a better place.

Such is the ethos of Seascape, which started in 2008 with a Mini-styled 18-footer and has grown to include a 24-, a 27- and a 14-footer. Along the way, and now several hundred boats later, Mihelin and his young and industrious employees have nurtured a devout clan of sailors in Europe, especially around the Adriatic and Baltic, where coastal racing in Seascapes is what the cool kids do. They’re also now kings of the Silver Rudder, which Mihelin explains to be the largest singlehanded distance race in the world, where as many as 450 sailors race 140 miles around the second-largest Danish island.

The Beneteau Group, I’m told, was impressed with the quality and ingenuity of Seascape’s Sam Manuard-designed boats and the whole Seascape schtick. The company came knocking a few years ago, keen to buy the brand, integrate it, and get back into the rank-and-file ­performance-sailing game with a new spin on its “First” lineage. Having finally figured out how to integrate the two companies, there is a long-term joint venture with Seascape overseeing Beneteau’s First and First Seascape Edition, including a weapon of a 36-footer that will debut by end of the year. Developing the new boat and the company behind it has all but consumed Mihelin, and when we finally meet in person, he confesses he hasn’t raced much lately—at least not at the level he used to. He admits to feeling unprepared, and he acknowledges we might not be competitive.

“I’m here for the adventure,” he says with a smile as we board the boat in unison. “I’m here to get outside my comfort zone, again. I need to do it. I miss it.”

Two days before our doublehanded ­division start, we dive right into our worklist, stripping the boat of clutter and sorting our safety gear before the inspector comes knocking. We pass, except for one thing: our safety-gear location map. The inspector asks where it is, and Mihelin points to a single hanging bag to starboard where all the gear is stowed. “It’s a small boat,” he says. “It’s all in here. Do we really need a map?”

Starting upwind in strong winds from Chicago, the race quickly transitioned to sea breezes and calms that required every sail in the ­inventory. Andraž Mihelin

Once cleared and done with the day’s boatwork, we cast lines and head out past the breakwater for our first sail together, hoisting the entire upwind inventory of new North Sails 3Di Raw to make sure it all fits. We have a full-battened main, an all-­purpose jib, a Code Zero and a bright-orange storm sail, which will double as a genoa staysail. We toss up the masthead spinnaker for good measure and leave the fractional below—that one will never see the light of day.

The exercise feels a bit rushed and ­chaotic, but it’s our only chance to feel each other out. My main concern is deciphering which ropes do what, but I discover the boat is nothing but simple and logical. Our only headsail is on a furler, so there will be no middle-of-the-night changes. The jib leads go up and down and in and out, and the asymmetric connects at the usual three places. Halyards and sail controls are all led to clutches on the coach roof—nothing fancy.

On the morning of the start, we meet early in a hotel room, connected on a laptop with a professional weather router in Europe who’s been crunching the models. For days, we have been glued to the Windy app on our phones, trying to predict the behavior of a high-pressure bubble that will be wobbling over the lake for the entire race. There will be a gradient. There will be sea breezes filling and land breezes draining. There will be upwind work to start, drifting in the middle, and a fresh VMG spinnaker run to the finish. There will be a little bit of everything our forecaster assures us as he shows limited routing options concentrated on the rhumbline. He warns us several times to be careful about getting too close to the shore at the wrong time of day. If we get stuck, we’ll be there for a while.

And with that advice in hand, we schlep our gear and a single food bag to the boat and take one last sweep through to ensure all is ready. We call our families and say our goodbyes before slipping lines and heading out for our 11 a.m. check-in. Without much time to waste, we loiter near the race-­committee boat and devise our strategy. The line is absurdly long for only four boats, so we agree to keep clear of the committee-boat magnets. The plan is to go east early, so we port-tack the start, harden up, and settle into a breezy and lumpy upwind groove.

Mihelin’s plan is to tack sometime after sunset, once we get our nose into the anticipated overnight shift. Everyone’s going the same way, and eventually we’re in among the Tartan 10s, lined with crews on the rail twiddling thumbs.

We skip dinner, but the family-size bag of GORP trail mix between my legs is all the gourmet I need. We trade places on the helm for pee breaks and backstretches, talking nonstop about family and work and our next challenge in life—deep stuff, right off the bat. We barely know each other, but we’re gabbing like a couple of frat brothers reunited after 20 years.

Once darkness comes, Mihelin insists we go straight into a two-hour watch system. He takes the first, and I settle in, my hand reaching into the feed bag and me choking down lukewarm sweetened Starbucks Via. I enjoy the silence, alone with my own thoughts of the days ahead and simply concentrating on keeping the boat tracking fast on course as the wind slowly veers and dies.

I wake Mihelin on schedule, and he steps on deck and jumps right into steering as if he’s been awake for an hour.

“I’ll leave you to it,” I say as I step below, strip out of my foul-weather gear, and collapse into the beanbag to leeward. With water sluicing past the hull inches from my ear, I plummet into the deepest sleep until I feel a tap on my leg, burst open my eyes, and only see a dark shadow through the companionway.

Who is this? Where the hell am I?

I quickly realize it’s my watch. I slip my bibs back on and step into the cockpit, where Mihelin shows me our position on the small chart plotter on a swivel arm from inside the boat. We’re just off Little Sable Point, a few miles east of rhumbline and still following the master plan—all is right.

He disappears below, leaving me to stare in wonder at the stillness of the night, a low moon veiled by smoke from faraway fires in Canada. There is barely 5 knots of wind, and with the boat sitting upright on its lines, it’s impossible to get any feel from the rudders. I sense my driving is erratic, so I try to find a place to sit comfortably and not oversteer. Finally, I slide down to the cockpit floor and rest my hand on the tip of the tiller. From here, I can see the dimly lit displays and ­listen to the gurgle of the transom.

A few hours later, as we swap watches again, the breeze continues to drop. As I wrestle my jacket into a makeshift pillow, all I can hear is a faint trickle of water passing by, lulling me into a deep sleep again until I’m awoken by stomping on the foredeck. I hear a sail bag drag across the deck, and I wonder whether I should get up and help. But he already has autopilot assist. It’s his watch; he knows what he’s doing. If needs me, he’ll wake me, I think to myself before nodding off again.

Soon after, I get a tap on my leg again, and then rise through the companionway to admire the golden and placid morning light. We’re barely moving. The foredeck action, I now see, was Mihelin hoisting every upwind sail we have. A triple-headed setup fills the foretriangle, but the genoa staysail is gently flapping in the slot, so that ­eventually comes down. The Code Zero is not doing much, except adding a bunch of drag, so that is scuttled too. We’re back to jib only.

As the day drags on, we crawl along under beautiful blue skies. The flies appear at lunchtime with an appetite of their own. Nemo—our friends on the other Seascape—is west of rhumbline and behind by a good 6 miles or so according to the tracker. Exile, the lead J/88, is sneaking away, and the other is somewhere directly behind us.

While we scarf down prosciutto and warm cheese on torpedo buns, the wind frees enough for us to hedge toward the coastline for what we hope will be a few hours of sea-breeze boost, so we hoist and unfurl the Zero again, crack sheets, and enjoy our quickened pace. It’s a glory day of sailing, and for our first and only sunset dinner on board, Mihelin lights the new Jetboil we’re required to have. Within minutes, we’re slurping warm and salty soup while the autopilot steers us true.

After dinner, Mihelin excuses himself for a quick nap as we creep ever closer to the coast. At dusk, I have my eyes on a large expanse of slick water ahead near the shore. My gut tells me we better tack sooner than later, but it’s not a decision for me to make, so I wake Mihelin, who joins me on deck to witness boats ahead drifting listlessly back toward the middle of the lake into nothingness.

Soon, we’re drifting ourselves. A single knot of boatspeed is all we can muster. I see a sliver of a wind line ahead, and suggest we chase it and hope for the best. “Wouldn’t it be amazing if we got one little zephyr to get out of here,” I say.

As if on command, a ribbon of breeze appears a few hundred yards ahead, so we carry on for another 20 minutes or so, enjoying our new speed and the heading breeze. Once we feel we’ve gotten the most out of it, we tack, running away from the shoreline at 4 knots. Behind us, the wind disappears. We laugh at our luck with the zephyr.

Once clear of Big Point Sable, Mihelin is confident in our course and returns below to finish his off watch, leaving me to the darkness again, in a surreal world of oily smooth water, abundant stars, and the hiss of water streaming from the transom. I feel as though I’m sailing across black ice, a magical experience that has me awestruck. I imagine myself a soloist in a Mini, letting the autopilot drive and soaking in every ­element of this unique moment.

Energized by my new surroundings, I’m tempted to carry on through the watch rotation, but I follow the code and eventually wake Mihelin, tapping his leg and delivering bad news: We’ve had a good pace over the past few hours, but we’re back to drifting.

The sun is soon up, hot and heavy, and the lake is a millpond again. Spinnakers hang limp on boats nearby. No one is moving, and ahead are Point Betsie and the Manitou Islands. As advised, we’ve kept our distance from Betsie, but not enough. To our west, Nemo is cruising past us at 5 knots to our 1, and over the next few hours, the tracker updates are depressing.

Our only hope is to chase what we think is a wind line to the northwest, so we abandon the rhumbline and crawl toward a faraway dark patch. Ripples finally appear in the late afternoon, and we set the masthead spinnaker for the first time. This is our moonshot. We know others are stuck near the coast, and out here in the middle there is no one with us. It’s possible we have sailed ourselves into oblivion. On the tracker, we’re last in our division by a good 6 miles.

We accept that there is no way in hell we’re going to win this race, but with the fresh new wind, a lazy following sea, and the finish line around the corner, the vibe subconsciously shifts. While we sail downwind, Mihelin tutors me on Slovenian culture, the young country’s history, and its competitive, adventurous and outdoorsy people. We share TED Talks nuggets and memorable sailing moments, and without even realizing it, we’re working the boat a lot harder, like two young sailors gleefully playing in the waves.

At one point, I enjoy a 9-knot surf and explode with delirious excitement.

“Beat that!” I challenge Mihelin, handing him the tiller extension.

He does, with a 10.2, and like a couple of dorks, we slap a high-five.

After a few more miles of this, we glide past Beaver Island as the sun sets and the southerly stirs tumbling whitecaps. Our sails are now fully loaded, and the boat gallops along at pace toward Grays Reef Lighthouse. Mihelin checks the tracker and reports we’ve actually closed on Nemo, shaving off a few miles. Maybe we have a shot at not being last.

Andraz Mihelin
Mihelin, now in charge of Beneteau’s First racing line, draws his memories and experiences from the solo Mini class, which is evident in his ­Seascape line of boats, designed for adventure racing. Dave Reed

So, we work the boat and sails a little harder, nail our first jibe of the entire race, and then start our exhilarating navigational slalom through the darkness, soaring out of my comfort zone and blissfully planing toward the lights of the Mackinac Bridge.

When we do finally pass under the metal-grated roadbed above, Mihelin rushes to snap a few blurry photos like a tourist refusing to pull over at the vista, and then two more smooth jibes later, we cross the finish line with a spotlight beam illuminating our port side. We’ve cut a 6-mile deficit to a mile or so, and hours down to merely 25 minutes to Nemo.

Mihelin reaches out to shake hands, but I’m too stunned to react. I’m not ready to stop. I can hear the raucous celebrations of cockpit rum squalls and the afterhours of the Pink Pony’s last call, but I’m feeling my inner Bernard Moitessier. It could be the adrenaline still coursing but, honestly, I just want Mihelin to put the spinnaker back up so we can keep on ripping into the ebony.