Good times never seemed so good on the island ⛵️🐴🍦 #cycrtm ...

That’s a wrap. Great race, Hollywood sailing Sunday afternoon then a blast reach down the straits at 14 knots and hitting 20 under a reefed main and No. 3. Quick one at 34 hours. Third in class! Most excellent crew, so proud of Will and Jack. #mainstreetsailing #cycrtm #lovemymainstreetcrew #ChicagoMacRace2022 ...

Had a blast in the race to Mackinac this year. Our team got line honours in our fleet (a big win for us!) with an elapsed time of 2 days, 8 hrs but unfortunately got corrected over and ended up in 5th place. Would have loved podium but happy with our performance all things considered. We had wonderful weather despite the bit of rain on Saturday and no flies this year! Still on a high... 😃⛵ #cycracetomackinac #cycrtm #sailing #sydney41 #lakemichigan #chicago #mackinacisland First photo credit to photographers of the #racetomackinac ...

🚨 Exciting Mac Race News! 🚨 To celebrate the Chicago Yacht Club’s 150th Anniversary, the Race to Mackinac is introducing a brand new course for 2025! For the first time, the new Skyline Sprint will have the fleet racing 5 miles along Chicago’s north lakefront offering stunning views for spectators along the way. With boats racing close to shore this is set to be one of the most thrilling races yet! 🌊🏁 “We’re thrilled to introduce the Skyline Sprint to both our competitors and fans, as well as to the public,” said Race Chairman Winn Soldani. “With over 300 boats racing close to shore in front of tens of thousands of Chicagoans, this will offer some of the most exciting and accessible viewing in the history of the Chicago Yacht Club.” Learn More 👉 link in bio #cycrtm ...

So far so good. Great first day of the Race to Mackinac for my 33rd race up Lake Michigan. Wetter and windier than advertised. But as we head into the Manitous danger lurks ahead. #mainstreetsailing #hopingthewindholds #lovesailingwithmypeople #cycrtm #pandorussphinxmoth racetomackinac ...

Post-race partying after six days of race committee duty for racetomackinac, and a tiny view of the minor chaos of docking 100+ boats at the island. Parties included a newly created brunch for first timers - both crew of new boat/skipper combos doing their inaugural race, and individual crew members doing their first Mac. Love the positive reinforcement for newbies. #cycrtm ...

And another Mac in the books. The good ship Main Street got us to the island in good form. And fast. Finished at 5 this morning before the wind went very light. Fun downwind race with a fabulous crew. #mainstreetsailing #cycrtm #sailingwithfamily #pinkpony #timetocelebrate ...