Arrival in Nfld before July first is going to be a bit chilly, and foggy. But June is a good time to see icebergs.
Nova Scotia is nice in June, but I generally keep the espar working, at night, until July first. But a sleeping bag and a sweater will do too.
If you're going to Nfld, a stop in the Bras D'or, Cape Breton, is usually in order; and
Sydney is the usual place to wait for a window to cross anyway. The Bras D'or Lakes is wonderful, and worth a month by themselves. But if you want to see much of Nfld, get there soonest, because summer is relatively short.
Have a great trip. Newfoundland is beautiful in summer.
There are several members of CF who live and
cruise in Newfoundland, with luck, they'll chime in.
Cheers.
Paul.
PS, to answer your question, leave the chesapeake the first of May, assuming you have lots of time. Leave from Newfoundland Mid August to Sept first for an Oct arrival back in
Baltimore. The trip south is usually best using frontal systems to get favourable winds for a speedy trip. Going south in the fall is quite nice, when you have 20 knots on the quarter, you can make good time with little fuss.
I've made the Cape Breton to
Bahamas trip 7 times, and always leaving
Halifax between Sept 15 and October 31. It's always been a great trip.
(5 trips
single handed, on my
Hughes 35, 2 trips with my wife, on my Corbin 39)