One Week in Maine: Lighthouses, Lobster, and L.L. Bean

By Hilary Nangle, author of Moon Maine

Maine’s biggest draws are the three L’s: lighthouses, lobster, and L.L. Bean. Maine’s 64 lighthouses stretch from York’s Nubble to candy-striped West Quoddy Head in Lubec. Lobster, of course, can be found practically everywhere along the coast, but the best way to enjoy it is at a no-fuss lobster shack. L.L. Bean’s ever-expanding campus in Freeport is the massive outdoor retailer’s mother ship, but it also has an outlet in Ellsworth.

This six-day tour concentrates on the Greater Portland, Mid-Coast, and Penobscot Bay regions. Book your first night’s lodging in Portland, the second two in Damariscotta or Newcastle, and the next two in the Thomaston-Rockland area. For a real lighthouse immersion, consider splurging on an extra two nights on Isle au Haut. If you’re arriving by air, use Portland International Jetport.

sunset on the rocky coast with a lighthouse — Portland Head Lighthouse. Photo © Sara Winter/123rf.

Day 1

Map of Downtown Portland — Downtown Portland

Try to arrive in Portland in time to enjoy an afternoon cruise with Lucky Catch Lobster Tours; perhaps you’ll catch your dinner. If not, you can still enjoy a lobster on the waterfront.

Day 2

Loop out to South Portland and Cape Elizabeth to visit Spring Point Ledge Light and Portland Head Light, a Maine icon. You won’t find a better setting for lunch than The Lobster Shack, with views of crashing surf and Cape Elizabeth Light. In the afternoon, consider visiting the Portland Museum of Art to view masterworks by Maine-related artists or book a sail amid the islands of Casco Bay. Still craving lobster? Try an inspired version by one of Maine’s nationally recognized chefs (reservations required).

Day 3

Get an early start and begin at famed outlet store L.L. Bean in Freeport. You might even take a Walk-on Adventure with Bean’s Outdoor Discovery School. In the afternoon, visit the Maine Maritime Museum in Bath, and if time permits, take a lighthouse cruise on the Kennebec River. Perhaps mosey down to Georgetown for dinner at Five Islands or stop in Wiscasset for a lobster roll.

Day 4

Boothbay PeninsulaSpend the morning in Boothbay Harbor, stepping back in time for a visit with light keeper Joseph Muise and his family on a Burnt Island Tour. In the late afternoon, drive down to Pemaquid Point to view Pemaquid Point Lighthouse, perhaps climbing to the top. Be sure to visit the Fisherman’s Museum in the keeper’s house. End the day with lobster in the rough in Round Pond.

aerial view of trees and houses on the harbor in maine — Boothbay Harbor, Maine. Photo © Visions of America LLC/123rf.

Day 5

Begin the day with a visit to Marshall Point Lighthouse Museum in Port Clyde, and then board the mail boat to Monhegan Island. Be sure to visit the museum in the lighthouse keeper’s house. Lunch? Lobster at Fish House Fish, of course.

Day 6

Greet the day with a sunrise walk out on the breakwater to Rockland Breakwater Lighthouse. Afterward, tour the Maine Lighthouse Museum and Farnsworth Art Museum. In the afternoon, take a lighthouse-themed cruise or sea kayak tour out of Rockport or Rockland. End the day and your lobster-infused vacation at the James Beard Award-winning lobster shack Waterman’s Beach Lobster in South Thomaston. En route, take the short side jaunt out to Owls Head Light in Owls Head.

Days 7-8

Splurge with a two-night stay at The Keeper’s House on Isle au Haut. The rustic accommodations are in the keeper’s house, oil house, and woodshed at Robinson Point Light, and access is via a passenger ferry.