Hey Tom,
You're welcome to steal from the wife's journals - 1999 and 2001 crossings from the CCC to Maine. They're at www.marenal.net
With the prevailing SW winds, I personally recommend the direct crossing from CCC to Tenants. Much easier if one or more have night sailing experience to get over some of the initial shocks - "What's that big red light to the East???" answer "It's the moon coming up."
Going back SW, it's a long (loooooong) slog to weather. Better to break it up into day long pieces, getting to harbor before dark. Of course, you may get a mini-NEaster & go direct. Did one return trip on a friend's boat (that I helped build) - made it from the harbor in Sandwich, MA to New London, CT in 11 1/2 hours, hitting 12+ knots steady during part of the trip!