This time around, the winds were strong and a storm was moving in. We ended up flipping the boat twice, tearing the sail and being towed in by a very helpful guy who happened to see us.
Actually three people made there way over to us and asked us if we needed help, including the owner of the rental company we got the boat from. We felt very safe, and well taken care of.
Here's a photo before the sail tore. It's much harder to get photos on a small sailboat when you don't have anyone in a kayak nearby :)
I'm not sure if I'd go sailing again, but I would definitely rent a canoe or kayak at Nicolet Beach in Peninsula State Park. We have camped at the park twice before and loved it. There are great biking trails, beautiful places to watch the sunset and it's in Fish Creek with lots of great dining options.