What kind of boat are you delivering and what is its cruising speed?
Do you have crew to do it in a straight shot, or are you planning on stopping for the night in anchorages
along the way?
If you'll be stopping (and even if you're not), you'll probably be transiting the cape cod
canal. Be sure to check the canal tide tables and plan your trip through it to go with the current
If it were me and I wanted to move quickly, but stop at night, I would do a long day (120miles) to P-town, the next day through the canal and a little under a hundred miles to Block Island, and the third day around a hundred to City Island. If you want a shorter first day, stop at Cape Ann (Sandy Bay, Anisquam, or Gloucester), then Cutty Hunk. If you wanted to go non-stop you're looking at about 300nm -- depending on the boat that is probably 1.5-2 days. If going non-stop I'd be inclined to go outside Cape Cod
Also, watch the weather
. The winds can come from any point on the compass
, but generally from the southwest that time of year. It'd be less fun motoring into the wind
the whole way, and if facing days of that I'd be inclined to either delay or do shorter days.