It’s the largest city in the state and as metropolitan as it gets, yet Portland is still a great place to begin a laid-back cruise Down East. Located on Casco Bay, where the sand beaches to the south give way to the rocky promontories of the mid-coast, it has a bit of an urban edge, yet Portland can still impart the feel of a smallish town, which is why it’s done a clever job of luring skippers away from the summer noise and crowds in places like Newport. And because there are so many moorings and marinas here, it’s a good location for boats of all sizes. DeMillo’s, for instance, is a full-service facility with about 125 slips and room for yachts up to 250 feet. It’s one of several first-rate marinas for boaters in a city that in recent years has transformed itself from an industrial town with a commercial waterfront to an active port with a walkable downtown and a thriving restaurant scene. There’s no doubt that Portland is for foodies, as it’s now home to well over 200 restaurants, as well as young chefs recruited from cities like Boston and New York. These pros are cooking up a variety of cuisines in addition to local seafood staples. But even so, in Portland you’ll learn that when cruising Maine, a lobster bib can be as indispensable as radar. At the Portland Lobster Company on Commercial Street, the chef still turns out about 500 lobster rolls a day.