This itinerary covers all of the state’s coastal regions in 14 days. Be forewarned: You’ll be doing a fair bit of driving on Route 1, the major thoroughfare that strings these sights together. It’s primarily a two-lane road, where speeds through towns are often 25 mph or below—not ideal for a speed trip along the coast. Although this itinerary is planned as 14 days, you’ll be rewarded if you spend longer in any of the locations, but especially on Mount Desert Island.
If you’re arriving by airplane, your best bet is to arrive at Portland International Jetport and depart from Bangor International. If you can’t swing that, use Portland only (which may require a 15th night in Portland). Book your first 2 nights’ lodging in Greater Portland, nights 3 and 4 on the Pemaquid Peninsula, nights 5 and 6 in Rockland or vicinity, nights 7 and 8 on the Blue Hill Peninsula or Deer Isle, nights nine, 10, and 11 on Mount Desert Island, night 12 in Lubec, and night 13 in either Lubec or Eastport.
Ease into your Maine immersion in Ogunquit with a refreshing walk along the Marginal Way or sunbathing on Ogunquit Beach, one of Maine’s prettiest, and proof that there’s plenty of sand along Maine’s fabled rockbound coast. Spend the afternoon in Kennebunkport, shopping in the boutiques and galleries that crowd Dock Square, enjoying a leisurely drive along the waterfront, or seeing the Southern Coast by boat.
Rise early and greet the day at Portland Head Light, a Cape Elizabeth landmark and Maine’s oldest lighthouse (1791). Wander through three centuries of art and architecture at the Portland Museum of Art. If you want to tour Winslow Homer’s studio, reserve through the museum well in advance. End the day with a sunset cruise on Casco Bay.
Make an early-morning pilgrimage to always-open gigantic sports retailer and outfitter L.L.Bean, hub of the hubbub in Freeport. You might linger and spend a few hours shopping at outlets or taking a Walk-on Adventure class before continuing to the Maine Maritime Museum, 10 acres of indoor and outdoor exhibits celebrating the state’s nautical heritage, in Bath. Be sure to make advance reservations for the museum’s B.I.W. trolley tour. Consider a stop in Wiscasset before ending the day on the Pemaquid Peninsula.
Take a day trip to Monhegan Island from New Harbor. This car-free, carefree gem, about a dozen miles off the coast, is laced with hiking trails and has earned a place in art history books as the Artists’ Island. Before or afterward, mosey down to Pemaquid Point Lighthouse. Alternatively, poke around the peninsula, visiting Fort William Henry, rolling up your sleeves at an authentic lobster shack in Round Pond, and browsing Damariscotta’s Main Street shops.
Days 5 and 6
Soak up the best of Penobscot Bay. Tour The Farnsworth Art Museum and Maine Lighthouse Museum. Perhaps walk out the nearly mile-long breakwater to Rockland Breakwater Light. You might nose over to Owls Head to view the lighthouse and see the Owls Head Transportation Museum, browse galleries in Rockland and Port Clyde, hop a ferry to Vinalhaven Island, sail aboard a windjammer, or tour Camden’s harbor on a sea kayak.
Days 7 and 8
Drive or hike to the top of Mount Battie, in Camden Hills State Park, for panoramic vistas over Penobscot Bay, and then head to the Blue Hill Peninsula. If you’re a history buff, head for Castine; if you’re an arts fan, explore the dozens of studios and galleries peppering the peninsula and adjoining Deer Isle; if you’re a hiker, plentiful preserves salt the region. You can even take a day boat to a remote section of Acadia National Park on Isle au Haut.
Few places in Maine rival Mount Desert Island and Acadia National Park for scenery and outdoor activities. After stopping at the park’s visitor center, drive the Park Loop, a perfect introduction to Acadia that covers many of the highlights. Be sure to welcome at least one day by watching the sunrise from the summit of Cadillac Mountain. After that, follow your passions: Go hiking, bicycling, or sea kayaking; take a carriage ride; attend a ranger session; board an excursion boat or a whale-watching expedition; visit Asticou Azalea and Thuya Gardens. Consider packing a picnic, hopping the passenger ferry to Winter Harbor, and spending the better part of one day in the Schoodic section of Acadia National Park.
Down East Maine beckons. En route to Lubec, loop through Cherryfield to ogle the architecture and browse the general store or down to Cutler to hike the spectacular trails of the Cutler Coast Public Preserve. Be sure to visit Maine’s candy-striped lighthouse at West Quoddy Head State Park, where you can tour the museum and walk the trail edging the seaside cliffs.
If you’ve brought your passport or passport card, spend the morning at Roosevelt Campobello International Park. Otherwise poke around Lubec before edging around Cobscook Bay to Eastport, home to some of the highest tides on the East Coast. (Note: If you prefer, you can spend a second night in Lubec and day-trip to Eastport via a passenger ferry.) Browse downtown shops and soak up small-town Down East life.
After catching the sunrise, drive to Bangor (allow at least three hours) for your flight home. If you have a late flight out of Portland, connect to I-95 in Bangor (allow an additional 2.5 hours). If you’ve added a final night in Portland, return via Route 1 and break in Belfast for lunch before continuing on to Portland.