I've circled Lakes Erie, Huron and Michigan by bicycle. I am really looking forward to my future tours around Lakes Ontario and Superior.
If I was starting out with a plan to circle all five lakes I would probably plan to circle the lakes in this order.
Lake Ontario ==> Lake Erie ==> Lake Michigan ==> Lake Huron ==> Lake Superior
There are numerous reasons for this order but one of them is that I've developed an appreciation for moderately remote areas with fewer of the trappings of modern civilization. With Lake Erie I was always within range of a major city during any point in the tour. Lake Michigan had a couple of remote areas especially when cruising through the hillier inland areas of Michigan and Wisconsin. Lake Huron had more areas where you could go for a long way away from large cities or even small towns.
You will have wildlife opportunities around any of the lakes. I saw lots of baby deer near Lake Erie, a black bear while going around Lake Huron and my stealth camp site was enlivened when a red fox passed through momentarily as the day's last light appeared.
All three of the lakes so far have been very scenic and I've had the opportunity to meet numerous nice people.
Manitoulin Island is moderately hilly. It is possible to obtain a detailed island map at local variety stores once you are on the actual island. The ferry ride to the island from Tobermory is very beautiful and should be experienced during the daylight if possible. Highway 6 or 8 heading south from Tobermory is busy, shoulderless and should be ridden with care. Island roads are relatively low traffic. If you continue north off the island then you will visit the Le Cloud mountains before you reach the TransCanada highways. Highway 17 should also be handled with care if you decide to continue around Lake Huron. A helmet mirror makes a real difference in my experience!
I dream of my future tour around Lake Superior. 1300+ miles of road to tour, lots of hills and mini mountains. Numerous remote areas and I am very likely to see wildlife along the way. To top it all off it's on the Cross Canada route so I might just find that most elusive of creatures, the cross canada cyclist!
Any questions, please ask!
~Jamie N