The Race to Mackinac has been run since 1898, when five boats set out from Chicago. Today it covers 333 statute miles up Lake Michigan, crosses into Lake Huron at the Straits of Mackinac, and finishes off Mackinac Island — and it is not an easy voyage. It is also not a gentle one. Sustained gales flattened big chunks of the fleet in 1911, 1937, and 1970, and after a deadly storm in 2011, the Mac’s reputation for danger stopped being theoretical. The fastest boats finish absurdly quickly now, with an all-time record of 18 hours and 50 minutes set back in 1998, but most crews are out there for two or three nights. The sailors alternate, sleeping in shifts of four hours each, until they (hopefully) make land.
It might seem tough to imagine doing that once — now, try doing it two dozen more. For those who make the journey at least 25 times, the prize is entry into the Island Goats Sailing Society, founded in 1959 and now several hundred strong. Rack up 25 Chicago Macs and 25 from Port Huron, and you become a Double Goat. The nickname, as the story goes, comes from the aroma a crew carries after days at sea with no shower. All things considered, this is a tough, electric, occasionally dangerous race. The Chicago Yacht Club hosts the race annually in mid-July, and that’s exactly where I went to look at watches.
The marketing around sailing wants you in a five-figure regatta chronograph, but with 2026 attendance at roughly 250 boats, I found what these sailors actually strap on is more interesting, from a cheap beater Timex to a shiny Rolex, and a lot else in between.
Citizen Eco-Drive chronograph
A busy, handsome black-dial chronograph, solar-powered so it never needs a battery, and worn by a man on his 20th Mac. Bob Kirkman’s was a gift from his wife years ago, and the case shows it — scuffed crystal, worn bezel, the honest patina of a watch that’s actually been somewhere.
It’s the kind of watch that isn’t necessarily flashy, but keeps showing up, race after race. Twenty Macs is five short of Old Goat status, which means Bob has a few more arrivals on Mackinac ahead of him. Odds are good the Citizen is going with him.
TAG Heuer 2000 Series Professional
Here’s the twist: Kevin Foote, who chairs the Race to Mackinac committee, doesn’t actually sail in this watch. Before a race, he hands the TAG — a handsome Swiss diver, the entry point to the brand for a generation — to his son to hold onto, and races in a more tech-forward watch instead, most likely a Garmin.
The TAG waiting at home is like a ritual that pulls him back safe. It’s a small superstition, and a telling one: even the guy who runs the race treats his good watch as something to come home to, not something to get soaked.
Victorinox Swiss Army field watch
From the maker of the Swiss Army Knife, and about as no-nonsense as its name suggests: a legible black field dial, a nylon strap, and zero pretension. Randy Weidenbusch has worn his for a decade.
He’s also sailing the Mac from both the Chicago side and the Huron side — it’s the kind of two-directional ambition that sailors love. The watch has already made the trip with him, which is pretty cool for a timepiece that costs a fraction of some other Swiss-luxury brands. Plus, with the slim design and low-case height, it’s not getting snagged on any rigging any time soon.
Rolex Yacht-Master II
Speaking of Swiss luxury — the fanciest wrist on the dock, and, fittingly, a pro’s. Chad Hough sails for Quantum Sails, and years ago someone bought him this Yacht-Master II (the big one, with the programmable regatta countdown and the deep-blue bezel) after a regatta win.
But look closer: he’s swapped the factory bracelet for a rubber strap, because rubber is simply better on a boat. That’s the whole story of watches and sailing in one wrist. A watch built to signify the sport, eventually modified by someone who actually does the sport, turned into something more than either. It looks damn good either way.
Marathon TSAR
Now we’re in pure tool territory. If you don’t know Marathon, that’s kind of the point — they’re a Canadian, family-run outfit that’s been supplying watches to Allied and NATO militaries since World War II, with the government contract numbers stamped on the casebacks to prove it. This is a defense supplier that happens to sell to civilians, not a fashion label doing a military look.
The “SAR” in their dive watches stands for Search And Rescue, the line’s actual issued heritage, and the tritium tubes on the dial glow on their own for years — no charging, no light source, just a faint permanent glow for reading the time at 3 a.m. mid-lake. If you look closely, you can even see the radioactivity symbol near 3 o’clock.
The owner, a guy who called himself RC, bought his a couple of years ago, and describes it with zero romance: a “standard 900-foot dive watch” that gets the job done. That is exactly the point. Nobody’s being precious over this watch on the water; it’s an instrument, and it’s built like one.
Timex Ironman Triathlon
From Japanese to Swiss to Canadian — finally, the great American watch brand. Timex traces back to the Waterbury Clock Company in the 1850s Connecticut, and by the 20th century, it had become the watch of the everyman: cheap, tough, and everywhere, built on the promise that it “takes a licking and keeps on ticking.”
The Ironman landed in 1986, named for the triathlon, and became the best-selling sport watch in America — a drugstore digital with a chronograph, lap memory, an Indiglo backlight, and 100 meters of water resistance, all for around $40.
Chuck Bayer has worn one on the boat for thirty years. Not the same one — he replaces them when they die — but that’s exactly the point. Chuck doesn’t baby it, doesn’t insure it, doesn’t think about it. He just swaps in a new one and keeps sailing. For a race this long and this rough, there’s something to be said for a watch you’d never cry over losing overboard.
Garmin quatix
Here’s the thing the luxury pieces won’t tell you: the most common watch on the dock wasn’t Swiss at all. It was the Garmin quatix, the marine version of Garmin’s outdoor GPS line, with a regatta timer that syncs to the real race clock, tack assist, and live boat data on your wrist. They were everywhere — if there’s a gold standard for actually racing the Mac, this is it.
Spencer Chanell summed up the appeal and the catch in one breath: it hooks into all the boat’s tech, but the interface is a little cluttered, because it’s trying to be a full smartwatch and a racing instrument at once.
Garmin quatix (2013)
Spencer’s friend Peter Malendowski offered the counterpoint from more than a decade earlier. He still races with the original 2013 quatix — black case, monochrome screen, none of the modern bells. “Not as advanced,” he told me, “but a good place to start.”
He’s not wrong. That watch was among the first wrist-wearables built for sailors, and every feature Spencer likes about his newer one started here. Two friends, two eras of the same watch: the modern tool that does everything, and the simple ancestor that did the four things that mattered.
The end of the race
There’s your spectrum: from a $40 Timex to a satellite-linked wrist computer, a Rolex that got moved to a rubber strap, and a lot else. The finish line for all of it is a place that hasn’t allowed a car since July 6, 1898.
Mackinac Island runs on horses (some 500 of them in summer), bicycles, and roughly 10,000 pounds of fudge a day. It’s the only state highway in America where motor vehicles are banned. Watches, though, are 100% welcome.
