But I wouldn't plan for it.
You're right, it just might need more time. Or maybe I could enlist my sons or friends as crew prior to the vacation to "deliver" the boat to MDI and leave it a week, then return back east in a one-way rental car with the wife and dog.
Then cap off the vacation with a cold front bringing 3 days of WNW winds in the 20's to sail back down though Buzzards Bay to Rhode Island at 10+ knots and then have it shift to the S so we could make Stratford CT (or west) in one tack.
Unfortunately life is rarely THAT good... but one can always be optimistic.