Not sure what you mean by wanting to "take a break" during July/August, but those are the months you need to be making hay if you're gonna cruise that region...

Are you absolutely committed to storing the boat in Maine? Perhaps laying up in NS, or even NFLD itself, might be an option? Would eliminate the necessity to backtrack the following summer, if you wanted to do more of NS... I suppose it might help to know what your thinking is for the following summer - do you plan to stay in New England, or head south, or whatever?

A number of cruisers winter their boats in Baddeck, the yards there are highly regarded - I believe Tim Allen has some experience with one of them... Also, NFLD has a number of Marine Centers - primarily for the commercial fleet there - that I've heard very good things about... But Baddeck would be marginally more convenient to travel to and from, and more experienced with yachts...