Our first bareboat charter (where we rent a boat and I’m captain) was in the Apostle Islands in Lake Superior in June 2020. We got the early season discount and we found out why when we had some chilly days. We didn’t have proper foul weather gear so at one point we were wearing all the layers we had, all at once. Our friend Teresa, a more experienced sailor, came with us and that was really helpful. We chartered a Jeanneau 33 which seemed huge to us at the time. The boat didn’t have a windlass or autopilot, and the reefing system we found to be cumbersome. This trip, like all our future trips, provided some context about what we wanted to look for in a boat.
I also went up to Lake Superior with my friend Jed for a class and we were on a Hunter 34 for that trip. Jed now has an Island Packet 27 that he and his family sail around Apostle Islands. It’s beautiful area to sail, and the islands are mostly wilderness. The downside is that it’s a shorter sailing season since it is north.
Here are some photos. There’s also a more detailed writeup in the PDF at the bottom of the page.
Also, here are some highlight photos:
SAILING ISLAND ZEPHYR 
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