Windy City sailor
I finally got around to upgrading (i.e. convinced my wife) from a vintage 1972 Irwin 23' to a beautiful, recently re-fitted 1972 C&C 35' Mk I. I sail on Lake Michigan out of Belmont Harbor in downtown Chicago, enjoying beautiful skyline views, especially for sunset cruises.
The downside of upgrading is that I can no longer say, "I have the cheapest sailboat in Belmont Harbor." The upside is that people no longer look at me as if they're eying a man on the verge of his demise every time I go out.
I mostly day-sail, single-handing about 50% of the time and bringing anyone from my family or another couple to a full load of beer buddies the rest of the time. We also do some weekend cruising, though, to the tourist/holiday towns scattered along the Lake Michigan shore.
Lucky for me, my daughter also has the sailing bug so she's always willing to turn on the charm to convince my wife that it's a great day to be on the water. The fact that we live five minutes from the harbor means also that going sailing doesn't have to be an all-weekend or even all-day affair, so I probably get on the water more days in my limited season that many people who live in more tropical climes.
It's bittersweet that the Chicago summer is so short, but as the joke goes, If it wasn't for the winters, everyone would want to live here.
1972 C&C 35'
1972 C&C 35' Mk I
Belmont Harbor, Chicago, IL