XJ....Still pretty early in the year for that trip. Dress warm.
Suggest you get a copy of the Waterway Guide Northern edition as it will give you good advice and the numbers of marinas and moorings you can use along the way. Are you gonna have crew or do the trip singlehanded?
Assuming you are gonna keep the traveling in daylight...there are plenty of places to pull in along the way. Some favorites include Newport RI, Cuttyhunk Moorings, Scituate Harbor Moorings. Salem Moorings. Portmouth NH is kind of a must stop on the way though expensive, and finally Portland is a nice town but I assume you know your way from there.
The only tough spot you need to plan for is the Cape Cod canal...with a brisk wind and tide against each other and all the traffic, it get get pretty damn uncomfortable. Be sure to plan your arrival there for slack tide and use the northward ebb to carry you along as it is a struggle otherwise.
Good luck with the trip and the boat. She should look real pretty on a mooring in Maine! As you do your planning check out www.marinas.com
for a closer look at the marinas along the way.