Route: Boston to Bar Harbor
Distance: 276 miles
Drive U.S. 1 from historic Boston Common to Salem (18 miles), where seagoing privateers easily outnumbered witches in the days gone by. Continue to Portsmouth, New Hampshire (shown here, 45 miles) and walk the Harbour Trail between North Church and the U.S.S. Albacore submarine.
Pit stop in the town of Kennebunkport (29 miles) from a rum-suffused "boat drink" at Heckman's Pub before a good night's sleep at the family-owned Nonantum Resort (rates start at $199).
Finish by heading through downtown Portland for some morning shopping (30 miles) before continuing up the Maine coast to Belfast (103 miles). There, Young's Lobster Pound is a great place to catch lunch before cruising into Bar Harbor (51 miles).