Most of the region’s attractions can be seen in clusters, with each group taking about a day to see. Spend the first day driving scenic Route 1, meandering past the antiques shops and other sights of York —including the impressive historic homes run by the Old York Historical Society —before visiting the Cape Neddick Light  in late afternoon, when the light is most dramatic. Ogunquit’s  crowded streets are best seen via its trolley system, so take one to Perkins Cove  and spend the morning shopping and snacking there, then walk back to the town center along Marginal Way . (Note that a handful of restaurants in town shut down in the winter off-season.)
In Portland , park your car and tour the Portland Museum of Art  in morning, follow it with lunch and shopping in the city, and then a drive to the Cape Elizabeth Lighthouse by sunset. Freeport’s L. L. Bean Factory Store  could easily demand the better part of a serious shopper’s day, but knock off by lunchtime, pick up some sandwiches, and put your newly bought hiking gear to the test on the trails of the Heath of Saco.