Re: Cape Cod Canal vs sailing around
We've gone both ways. If your plan is to hop along the coast, or even just do an overnight deadhead to anyplace in Maine, definitely go through the canal. If your plan is for an initial landfall in Nova Scotia, then going "around" the outside is an option, but you need to plan on 2 (unless you are wicked fast!) or more nights offshore before initial landfall if you are headed towards Yarmouth, Lunenburg, Shelborn, etc. Draw a rum line from NS to the canal entrance...NS is a lot of East, not so much North. If you decide on the outside trip, check the weather, there's no place to hide on the back cape, and you'll be a bit offshore for the rest.
Either way, check currents for the canal and/or Vineyard/Nantucket sound.
Best of luck with your trip.