From Freeport, get on US 1 toward Wiscasset, voted the prettiest town in Maine, with high-end antique shops. Just before Bath is Popham Beach, one of the few sand beaches in the state. There’s also a Civil War fort and the offshore Goat Rock, accessible at low tide. The next peninsula east offers Georgetown, Five Islands, and Reid State Park–another fine sand beach. Georgetown boasts the Grey Havens Inn–old fashioned, romantic, and highly recommended for a true "Old Maine" experience. The unbelievably scenic Five Islands is home to the state’s most famous lobster pound.  

East down the next peninsula is Boothbay Harbor–a lovely town with a charming harbor, sailing, great shops, and B&Bs. DO NOT MISS the Cabbage Island Clambake Cruise.  Maine’s most famous island is the wild and remote Monhegan Island, reached via boat from Boothbay. Monhegan offers stunning views over the open Atlantic from towering rock cliffs. 

Admire the art of Andrew Wyeth at the Olsen House in Cushing, where Wyeth painted “Christina’s World” and other famous paintings  These take the sugar coat off Maine and give a strong feel of the “other” Maine life rarely seen by visitors: hard work, poverty, isolation, and fierce independence. For more Wyeth art, stop at Rockland's Farnsworth Museum. Then take US 1 east to Camden—the Carmel of the Maine coast, with upscale shops, sailing trips into Penobscot Bay, a dozen picturesque B&Bs, and the climb up Mount Battie–inspiration for the famed Edna St. Vincent Millay poem, Renascence, which begins: “All I could see from where I stood was three long mountains and a wood; I turned and looked the other way, and saw three islands in a bay.”