Ill pass a few things I've learned about the northeast area, girectky dnd indirectly (others accounts)

Martha's Vineyard and the Elizabethan Islands can produce some serious current/chop and swell and it could prove quite the hazard in these conditions. I'd heed a pilots cautions in these areas. 

Camp cruising is funny. Funny in that for the most part your left alone and as you know, pack out what u bring and be gone by sunrise. The islanders (not long islanders) can sometimes even guard their property jealously. Private  islands I don't bother with even to stretch  and stand up - even with the department of environmental protection encouraging the islands shoreline fishing use. I just don't need the bad vibes when its my special  time.

Other than that you should be ok. Keep in touch dnd post your experiences here !

Pete

Buzzards Bay can get extremely choppy even on a sunny summer afternoon, and don't try a run through Woods Hole without a big motor. I once got stuck in current off West Chop for six hours in a 42-foot ketch with a broken transmission. -Wes

My wife and I did a nine day MITA trip last august in our NE dory and had an absolute blast.  We cannot wait to get out there and do it again.  Our trip wasn't very ambitious--we mostly sailed/rowed for half the day and then explored an island/relaxed.  We were lucky in that we had perfect weather.  One could get fogged in for days on the Maine cost in the summer.  

We posted a video to this list a few months ago of our trip which has more details of our route.  You can find it by searching for "boatymoon" on youtube.  The video below was also an inspiration.  

Good luck!

https://tinef.wordpress.com/2011/09/06/vinalhaven-circuit-the-movie/

Anyone considering a clc sailboat should check out the "Boatymoon" video on youtube.  It really gives a good idea of what you can do in the dory.

Looks like a lot of fun!

Since you mentioned a cruising Skerry I think you might be interested in a version that will hold plenty of gear and two people. It was the original Adventure I used by John Guider on his circumnavation of the US on the Great Loop. I'm ordering one exactly as this one for a bit under $1400 -all CNC cut panels only and with no epoxy-fiberglass or any other kit parts. It has more beam than the regular Skerry and covered decks. Needless to say the sail will be extra also. Contact Joey at CLC for more information. Also the panels will be one off so probably not any hand holding - but the hull itself will probably follow the regular Skerry assembly steps. I hope to start the build in January and will post my progress regularly.