Start the day with breakfast at Becky’s Diner, a waterfront institution. Aim for an outdoor table with a harbor view. Keep with the theme by ordering a lobster and Swiss omelet or indulge in another Maine favorite, blueberry pancakes—do splurge on the real maple syrup.
After breakfast, walk along Portland’s working waterfront taking in the action before joining the 10:30 am Portland Headlight Lobstering cruise with Lucky Catch; do make advance reservations. Not only will the captain explain everything lobster, he’ll also invite you to don oilskins and help haul, empty, and bait traps. The 80- to 90-minute cruise passes six lighthouses as well as coastal and island forts. Upon docking, mosey the short distance to Portland Lobster Company for lunch.
Loop through South Portland and Cape Elizabeth to visit some of the lighthouses viewed from sea by car or bicycle. If you lack wheels, join Portland Discovery Land and Sea Tours on its Portland City and Lighthouse trolley tour. It doesn’t take in all the lights mentioned below, but the guide will share info about Portland’s history and point out many of its sights, including the opulent Victoria Mansion and the boyhood home of poet Henry Wadsworth Longfellow, before heading to Cape Elizabeth for a 30-minute visit at Portland Head Light.
South Portland harbors two lighthouses. First stop, Bug Light Park, home to Portland Breakwater Light, nicknamed Bug Light due to its size. Modeled on an ancient Greek monument and built in 1875, the cast iron lighthouse offers smashing views of Portland’s skyline. While here, visit the small, South Portland Historical Society Museum. During World War II, New England Shipbuilding Corp. built 236 Liberty Ships on these grounds. A 35-foot-high by 65-foot-log Liberty Ship memorial honors that history.
Find the caisson-style Spring Point Ledge Light on the nearby campus of Southern Maine Community College. Admire it from the shore or hoof along the 900-foot granite breakwater for a closer look as well as panoramic views of Casco Bay. Volunteers usually man it on weekends and Tuesdays. Poke around the ruins of Fort Preble or stretch your legs on the 3-mile Spring Point Shoreline Walkway, which ends at Willard Beach.
Next, head to neighboring Cape Elizabeth. Portland Head Light, commissioned by President George Washington and first lit in 1791, is on the grounds of Fort Williams, a former military base turned town-owned, 90-acre oceanfront park with walking trails, tennis courts, playing fields, and ruins to explore. Walk around the lighthouse tower, admire the views to distant Ram Island Ledge Lighthouse, check out the memorial for the Annie C. Maguire, shipwrecked on the ledges below the light on Christmas Eve, 1886, and tour the museum in the restored keeper’s house. If you’re hungry, the Bite Into Maine food truck earns fame for its varieties of lobster rolls.
For more delicious views ocean views, visit 41-acre Two Lights State Park, named for Maine’s first twin lights, one 17 miles out to sea, the other nearby. Clamber around the battery ruins and rocky headlands to work up an appetite, then continue down the road to The Lobster Shack at Two Lights, sited on a rugged and rocky point about 15 minutes from downtown Portland, for a double header dinner. This classic Maine lobster shack has been serving lobsters, chowders, stews, and fried seafood, along with rave-worthy desserts, since the 1920s. Dine inside or outside, enjoying views of Cape Elizabeth Light and pounding surf and squawking gulls as background music.
If you want to see a moose, detour over to Len Libby, home to the world’s only life-sized chocolate moose. No, it’s not alive, but it’s is a moose, and while here, you can sweeten your life with house-made ice cream and chocolates.
Cap the day in Freeport, home to the L. L. Bean campus, along with dozens of factory stores and outlets. The flagship store never closes, and rock stars or other celebs visiting Portland usually shop in the wee hours of the morning. The downside of moonlight shopping is that none of the other Bean stores, including the outlet, or any of the other shops are open.
If by some strange chance you haven’t head your fill of lobster yet, you have two more options: Harraseeket Lunch & Lobster on the harbor in South Freeport, or Day’s Crabmeat & Lobster on a tidal estuary in Yarmouth.
Where to Stay in Portland Maine if you only have one day
The upscale, full-service, boutique-style Portland Harbor Hotel, offers a great Old Port location just one block from the waterfront.
The Chadwick, a four-room bed-and-breakfast in a quiet West End area, charms guests with personal service, great breakfasts, and stylish rooms.
Watch lobster boats bobbing in Kettle Cove from the especially eco-conscious, full-service, beach-front Inn by the Sea in Cape Elizabeth.