You'll love the Apostle Islands!
I agree with Capn Bruce. Get the Bonnie Dahl cruising guide, it is an excellent resource. We have been sailing in the Apostle's the last two years now and we love it. If you would like to see some pictures, check out my webshot albums. There are three different albums with pictures of the islands and anchorages we have visited. It is truly one of the most beautiful places I have ever seen. You mention you are coming from Kentucky. If you are looking to provision in town, it is no problem. Bayfield has a small grocey store and a liquor store. There is a much larger grocery store in Washburn, a small town about 11 miles south of Bayfield. If you looking to launch and don't need crane service, you might consider launching from Washburn rather than Bayfield although there is a launch ramp in Bayfield but I think Washburn is slightly better. If you are looking for transient dockage while in the area, please consider Pike's Bay Marina. It is the marina my husband and I keep our Hunter 34, the Jolly Swagman. PBM is the nicest marina in the area with the best clubhouse and bathrooms. Gordon Ringberg is the marina manager and PBM always stands by on vhf16. I'll give you my email address and if you come up next summer, please let me know. My husband and I would love to meet you.Sandra.huonder@unisys.com