You might want to consider getting a seasonal mooring/slip somewhere and using that as your base. Marina space for your boat would be about $3,500-$4,500 for the season. A seasonal mooring would run $1,000-$1,500. As I am sure you recall, the farther east you go the fewer marinas and other amenities you will find (basically none east of MDI in Maine).

There are marinas in southern Maine and the mid-coast, but once you get past Boothbay the pickings for dockage get slim. Marina space on a nightly basis will likely run $100 to $150 including power. Moorings will run $25 to $45 per night depending on location and services available. Weekly mooring rates will run $150+ and will not be available everywhere. So if you plan on being at a dock 7 of each 14 days you can expect to spend $400 to $650 per week for mooring/dockage or about $6,000 to $9,000 for your 100 days. Anchoring out will drop those cost