I LOVE Portland, Maine. I’ve been there twice now (once in 2007 and again in 2011). It’s one of many beautiful small cities to which my wife has introduced me. It’s not very far from our house near Worcester. Maybe two hours by car, plus we get to drive through New Hampshire on the highway and you know what that means: ridiculously cheap liquor and wine. We usually pick up a bottle of Cupcake Sauvignon Blanc for $9.99 and make that the pickup for the trip. Then, we’ll get some bottles for the house on the way back.
Portland itself is all New England. Right on the water with plenty of clam shacks. But, also a bit urban with limited parking and plenty of tourist trap shops. In that way, it’s a slightly more urban version of Mystic, Connecticut (hometown). Maybe that’s why I like it so: it’s familiar and comfortable.