Took a non-planned trip from Yarmouth to Lunenberg to Halifax to PEI to New Brunswick & then back thru Maine in 2003, early August.
In every reasonably sized town in NS and PEI (I forget about NB) , the Canadians are nice enough to run Hotel/B&B finders services. I forget what their name for them is called... Usually college kids or old geezers, but these folks are just there to help you find a hotel room that you like. Free service, also good to get the local rap on things to do, places to go, good restaurants, etc. They are there just to help you find a place to stay. The one in Lunenberg directed us to a B&B run by some pretty wild (for Canadians) ex hippie ex corporate types. We got along great, shot the breeze for hours & hours, and got told some great stories we wouldn't have heard any other way. The one in Halifax got a room in a great hotel at a discounted price in just the right part of town.
The way we travel when touring is: ride till you don't feel like it anymore, look for a place to stay, find the best restaurant, then crash & do it all over again. The only thing we plan in advance is the major stops & even then they are pretty flexible.
When in PEI, we just found the PEI 'Potato Museum' by dumb luck. While a bit cheesy, that sort of stop is, for us, one of the things that make MC touring all the more memorable. I now know more than most folks about the history of the potato & it's travels around the world.
Oh, and if you hit PEI just right, you'll be treated to miles & miles & miles of light perfume from the flowering potato plants...