Split from http://chowhound.chow.com/topics/683364 to fit in Southern New England, original is in Northern New England - The Chowhound Team
Portland's definitely pushing the "no more than four hours away" limit. I'd go to Providence, RI. It's in the Ocean State, so beaches abound, there are amazing restaurants of all ethnicities and pricepoints and some really nice hotels. The city itself is broken into many different eating sections: Federal Hill for Italian, East Side for just about anything you're looking for, West Side for funkier bistro-ish joints, Downcity for the steak houses and a couple higher end places, as well as lots of bars and cocktail spots. Don't quote me, but I bet there are around 150 restaurants/bars/takeaways in PVD.