Re: best time for cruising the 1000 islands?
I would lean toward early September since the crowds are gone, better winds, and generally decent weather. If going earlier check the date of the 1812 Overture by the Kingston Symphony. Great fun with real cannons and perfect setting.
Finished the circumnavigation in early February in Grenada. Have to work on a book project for the next several months so the boat will be waiting for next year.