The Chesapeake is always pretty special. Lots of places to go/see, lots of things to do. If you like anchoring, you might have a glance at Bill Shellenberger's "Cruising the Chseapeake: A Gunkholer's Guide." And of course there are the various cruising guides.
OTOH, it's usually pretty HOT and MUGGY around here in July and August (although not at all unbearable), so the best months are maybe April, then May, June, Sept, Oct, and Nov. Which in turn suggests further north in July and August could be pretty nifty. We haven't done that yet, but might aim for it next year.
We really liked living in Florida year round when we were working in Miami and living nearer to Ft. Lauderdale, but when boating from up here... it makes more sense for us to aim for warmer weather down there when cold weather is up here. No matter higher rates due to "the season" or not. (Within reason.)
-Chris
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Chesapeake Bay, USA
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