Fuel polishing would be recommended, especially if it's been sitting a couple years.
Winds that time of year can be too much or not at all between Maine
Transported my new/old boat from Maine
to Narragansett Bay last year and did a lot of motoring.
There are enough ports
along the way if you have to run from a tropical depression but not all are good hurricane
holes, most of the major ports
have options but the smaller ones can be a bit tight in a bigger boat.
Bring good charts
, there's some tricky navigation
on this route
depending on which way you decide to go as well as plenty of commercial
Traveling at night or anchoring
Just holed up in Block Island recently during the first named tropical storm of the season, no problems for me but for some with less than optimal ground tackle it was exciting, several boats broke free and flew across the anchorage, the local Safe Sea operator had a profitable day. If you do decide to set off in dodgy weather
just make sure you already have good, protected anchorages
Get a good cruising guide, just in case you need support services.
The trip your looking to do is a pretty nice sight seeing trip if the weather
cooperates, if not it'll be a long bash to windward.