Chicago to Mackinac: Big Gains, Bigger Reminders
JULY 2025 • CHICAGO YACHT CLUB RACE TO MACKINAC • SYDNEY 41 ‘UNKNOWN LADY’
The Chicago Mac started on July 19th in a light southwesterly breeze. For the first time, the race committee set a turning mark close to shore, giving spectators a better view of the fleet at the start.
We didn’t sail particularly well to that first mark and exited the harbor mid-pack. As the fleet stretched out across the lake, we found ourselves south of Point Betsie, not precisely where we wanted to be early on.
Looking ahead through binoculars, it was clear that the boats closer to shore were struggling in lighter air. We made a tactical decision to tack to starboard and stay farther out in the lake, betting on stronger gradient wind.
It was the right call.
We held that offshore arc for about six hours, then tacked back toward Point Betsie around 3:30 am. The payoff was immediate. Boat after boat slid backward relative to us, and we went from tenth in class to first, passing the entire group that had hugged the shore.
The crew felt good—and they should have. It was smart sailing.
Then reality stepped back in.
As we approached the Manitou Passage, the breeze picked up, so we needed to change the headsail. That’s when we discovered that the prep work on the furling system hadn’t been done properly. What should have been a controlled sail change turned into 40 minutes of sailing bareheaded, trying to sort out gear that should have been ready before the race ever started.
At that point, we were probably still leading on corrected time—but our comfortable margin evaporated. By the time we were moving again, the lead was razor-thin.
Near Gray’s Reef, sailing close-hauled, we never found a clean lane through the passage. Current, wind shifts, and traffic all worked against us, and boats from behind began to roll past. Once again, we gave back hard-earned gains.
We finished fifth in class.
Why This Matters for the Golden Globe:
The lesson from Lake Michigan was simple—and it applies everywhere, from buoy racing to the Southern Ocean.
Preparation matters more than potential.
Tactics matter more than talent.
And boats don’t fail races—unprepared crews do.
The Sydney 41 Unknown Lady was a capable boat. The crew was good. The sailing decisions were often right. But minor lapses in preparation—halyards, furlers, systems that hadn’t been fully vetted—cost us real positions in both races.
For the Golden Globe Race, there is no room for that.
When I look back on that summer, I see value, not disappointment. Sailing the Queen’s Cup, the Port Huron–Mackinac, the Chicago–Mackinac, and the Verve Cup gave me three major races and multiple crews, boats, and systems to evaluate. It reinforced habits that matter offshore: preparation, redundancy, and absolute familiarity with your gear.
It was a good summer. A busy one. And an important one.
With the Golden Globe just over a year away, I left Lake Michigan feeling sharper, more focused, and reminded—once again—that success at sea is earned long before the start gun ever fires.
