Portland: 106 miles N of Boston
Maine's largest city, Portland sits on a hammerhead-shaped peninsula extending into scenic Casco Bay. It's easy to drive right past on I-295, admiring the skyline at 60 miles an hour, and be on your way to the villages and headlands farther up the coast. After all, one doesn't usually think of urban life when envisioning a vacation in Maine.
But Portland is well worth an afternoon's detour or even a weekend stay. This historic city has plenty of charm -- especially the renovated (and touristed) Old Port, with its brick sidewalks and cobblestone streets, but not only there. Travelers who stop in Portland are also rewarded with ferries to offshore islands, boutique shops, historic homes, architectural treasures, graceful neighborhoods -- and top-shelf dining. Portland is the culinary mecca of northern New England, blessed with an uncommonly high number of excellent restaurants for a city its size.