home port in northeast

[Mike western MA]

Hello,
I am in the process of purchasing a wooden H28 which is currently berthed in Southport, CT. I live in western, MA - just under 2 hours to bridgeport, 2:40 to Stonington, 2:40 to many spots on narragansett bay, 3 hours to new bedford, etc. I hope to ultimately end up in eastern maine as my wife and I get closer to retired, but need an easier port to sail out of for the next few years. I'm wondering what people think of various harbors, marinas, etc. and what the availiblity of space is there. Most of our sailing will be weekend in spring/fall and a few days at a time in summer. My concerns are: 1- easiest possible drive, 2- security for boat, 3- most interesting sailing, 4- cost as modest as possible. I'll probably have it hauled to my home/shop for the winter, so storage isn't as important.

thanks, Mike