In Chicago, I sailed on Wings, a C&C 35-3 yacht, as well as other boats from 420s to wooden schooners (plus a tall ship, of which the story is here). 

But the first ever time I sailed in my whole life was when I joined the University of Chicago sailing club. In the club, we sailed on 420s, as is illustrated in the first two pictures, taken during a college regatta in which I participated. The remaining photos are from my occasional sails on various boats owned by my Chicago sailing friends. 

When I was asked about my motivation for joining the University of Chicago sailing club, I said I wanted to begin learning how to sail in order to be able to one day sail on a historical tall ship. They looked at me like: "Yeah, dream on!" Well, some 8 months later, I joined one of the finest racing yachts in Chicago. This was Wings, which is featured below. And some 15 months after my joining of the UOfC club, I started with my first tall ship, the Bounty (see here). While I was a regular crewmember on Wings (mostly working the mast, but also trying out the bow, as illustrated below), we celebrated many impressive victories and placements (Wings also because "Boat of the Year" during that era). Her " Chicago era" is unfortunately over now, however. She returned to her birthplace by Toronto, now sailing on Lake Ontario. 

Only a memory is now also my participation in the Mackinac Island Race. See the first picture for a rhumb-line of the course, which would be 333 miles long if it were possible to sail the shortest possible route. Even then, this would constitute the longest existing freshwater sail race (for more details, see here.) Starting from Chicago in the afternoon, and sailing days and nights, under the burning sun as well as through gales, the fastest boats arrive at the Mackinac Island finish line (marked by the red lighthouse) in the morning of the third day. 

Then some take a vacation to sail their boats back to Chicago, while others hire people to deliver their boats. Either way, that just meant more fun for me :-). The first picture in the row below, which I took on the way back, was the winning entry in a photo contest, which took place in conjunction with the 2006 Mackinac Island Race.