Great Lakes Charters
We have chartered with these operations and recommend them:
Superior Charters south of Bayfield, WI for the Apostles. Great anchoring on pink sand beaches in the mostly natural and beautiful islands of the Apostles National Shoreline. And the swimming was warm and pleasant in the shallow beaches.
Canadian Yacht Charters in Gore Bay on Manitoulin Island is a first class operation in the North Channel, one of the most beautiful, and natural cruising grounds in the world with hundreds of anchorages, and stunning pink granite. Oh, yeah, and great blue berries!
Anacortes Yacht Charters, a Moorings affiliate for the San Juans. Great, well managed anchorages or moorings, some fun quaint towns, and orca, seals, bald eagles, otters, crabs, sea birds, dolphins...
Kingston, Ontario is a sailing center with a fun downtown. I forget the name of the company we chartered with (the C&C 30 was just OK) but this is a gateway to the Thousand Islands, another large and interesting cruising ground that is much more developed, but still offers peaceful anchorages, along with Theater, and other attractions in the many towns ashore.
Our Lake Erie Islands stretch north from Sandusky to Leamington in Canada. Good marinas on mostly touristic Islands, with some fine anchorages off sandy beaches. A little crowded on the week-ends, but great during the week. (And we still enjoy quiet anchorages after the power boaters head home on week-end afternoons.) I don't know of a charter operator I can recommend, though. And Cedar Point on Sandusky Bay is a first rank amusement park if you have older kids. I just Googled these folks:
http://www.fairwindsailing.com/sailing_charters_lake_erie.html
I have no other knowledge of them, but they are in the right place!
Here is our blog of our cruise around Lake Erie, and in the Thousand Islands a couple of years ago:
http://jojofoster.livejournal.com/?skip=20