I find the run from from Cape Cod canal to Gloucester to be a decent day's sail. I usually drop the hook in Onset for the night since there really isn't a good place near the northeastern end of the CCC. Depending on the current you either have to leave near dawn or can laze about for part of the morning before getting underwayMake sure you have Eldriges or some other reliable current table. As long as you miss the middle four hours of the foul current you should be OK if you have a reliable engine (you can't sail through the CCC, you have to go through under power). From the CCC it is an easy day's run to Gloucester or if you get underway real early you can make Isles of Shoals before nightfall.