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

Maine’s biggest draws are the three Ls: lighthouses, lobster, and L.L. Bean. This six-day tour concentrates on the Greater Portland, Mid-Coast, and Penobscot Bay regions. Book your first two nights in Portland, the second two in the Damariscotta area, and the final two in Rockland. 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

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, book a sail or cruise to view the lighthouses salting Casco Bay.

Day 3

50 miles/80 km; 1 hour

Visit the Maine Maritime Museum in Bath, and take a lighthouse cruise on the Kennebec River followed by a mosey down to Georgetown for lobster on the wharf at Five Islands Lobster Company.

Day 4

35 miles/56 km; 50 minutes

View lighthouses on a cruise with Cap’n Fish’s departing from Boothbay Harbor. Or loop down to Pemaquid Point to view Pemaquid Point Lighthouse, before enjoying 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

40 miles/64 km; 1.25 hours

Book a daylong excursion to Monhegan Island aboard the Hardy Boat out of New Harbor. Be sure to visit the museum in the lighthouse keeper’s house. Lunch? Lobster at The Fish House, of course.

Day 6

50 miles/80 km; 1.5 hours

Greet the day with a walk out on the breakwater to Rockland Breakwater Light. Afterward, tour the Maine Lighthouse Museum. In the afternoon, take a lighthouse-themed cruise or sea kayak tour out of Rockport or Rockland. En route to yet another lobster dining experience at McLoon’s Lobster Shack in Spruce Head, take the short side jaunt out to Owls Head Light in Owls Head.

Hilary Nangle

About the Author

Despite brief out-of-state interludes for college and grad school (and a stint as a ski bum), Hilary Nangle has never been able to resist the lure of her home state. She grew up on Maine’s coast, spending much of each winter skiing in the western mountains. Her sense of wanderlust was ignited when she became a Registered Maine Whitewater Guide on the Kennebec River, which gave her a chance to explore the central and northern regions of the state.

When she tired of her parents asking when she was going to get a “real job,” Hilary drew on her writing skills and began seeking out editorial work. She started out editing pro ski tour publications, then became a managing editor for a food trade publication and a features editor for a daily newspaper. Now, she freelances professionally for national magazines, newspapers, and websites.

Hilary never tires of exploring Maine, always seeking out the offbeat and quirky, and rarely resisting the invitation of a back road. To her husband’s dismay, she inherited her grandmother’s shopping gene and can’t pass a used bookstore, artisans gallery, or antiques shop without browsing. She’s equally curious about food and has never met a lobster she didn’t like. Hilary still divides her year between the coast and the mountains, residing with her husband, Tom Nangle, and an oversized dog, both of whom share her passions for long walks and Maine-made ice cream.

For updates between editions and to follow Hilary’s travels, visit mainetravelmaven.com.

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Image of lighthouse at sunset with text One-Week Maine Itinerary