Day Trips from Boston to Kennebunkport

Escape Boston for a full day along the southern Maine coast, blending scenic seaside walks, historic harbor towns, and iconic lighthouse views. Begin at Marginal Way in Ogunquit, a cliffside coastal path that winds along the Atlantic with uninterrupted ocean views and classic New England scenery. Continue to Kennebunkport, a postcard-perfect harbor town known for its historic homes, local boutiques, and working waterfront. Arrive in Portland in time for lunch in the Old Port district, where cobblestone streets, 19th-century brick buildings, and fishing piers set the scene for some of Maine's best seafood — this is the spot to try fresh, locally caught lobster on your own. Finish at Portland Head Light, Maine's oldest and most iconic lighthouse, perched dramatically above the rocky shoreline within Fort Williams Park, with sweeping Atlantic views to close out the day.