Gloucester is a good call for a fisherman- you can walk around down there and check out the commercial fleet, go into the Crow's Nest and have a drink in the bar from "The Perfect Storm". Right outside of town is the famous statue with the names of those who have died at sea- that's pretty cool to see.
Salem is an interesting place- it's pretty much halloween year round there. If you're there around sunset, head to Pickering Wharf and pick up the boat shuttle to the Rockmore floating restaurant- decent food and drinks (though expensive), but right in the middle of Salem Harbor with scenery that can't be beat. There are usually big stripers that hang around the dock too...

If you get a bit north of there, go to Woodman's in Essex- the best New England fried clams you can get.
If you get north of there, Newburyport MA is a cool little town to walk around in.
And if you get north of there, shoot me a PM and it'd be my pleasure to buy you a beer in my town of Portsmouth NH.
Shoe