Cape Ann, half an hour up the coast from Boston, is the setting for Beauport Hotel Gloucester, a substantial seaside that presides over America’s oldest port town. The style is classic New England maritime, and the rooms and suites are as comfortable as they are handsome; the best suites come with fireplaces and direct ocean views. 1606 Restaurant & Oyster Bar is named for the year the settlers first mapped the port, and it specializes in fresh Atlantic seafood, served with an impressive ocean view. There’s also a rooftop bar, along with a swimming pool, an ideal venue for a summertime sunset.