Begin your day at $3 Dewey’s, a beloved Portland institution known for its casual atmosphere and hearty fare. Enjoy a classic breakfast or brunch and perhaps a mimosa to fuel up for the day ahead.

People are dining and socializing at outdoor tables in a narrow alleyway beside brick buildings under colorful shade sails at 3 Deweys, Portland, Maine’s original ale house. There are plants and a Shipyard sign in the foreground.

🦞 Midday Munch: Portland Lobster Company

A short walk from Dewey’s, the Portland Lobster Company offers a quintessential Maine experience. Situated on the waterfront, this spot serves up fresh lobster rolls, steamers, and chowder, all with a view of the harbor. It’s the perfect place to savor local seafood while soaking in the maritime ambiance.

A tray with a lobster roll, French fries, a pickle spear, and a lemon wedge—classic Maine flavors. The Portland Lobster Co. logo is visible on the bottom right, perfect to pair with a cold Shipyard beer.

🍺 Afternoon Sip: The Porthole

Continue your crawl to The Porthole, located on Custom House Wharf. This waterfront bar and restaurant is known for its lively atmosphere, live music, and extensive seafood menu. Enjoy a cold pint and perhaps a lobster roll while watching the boats go by. The Porthole embodies the essence of Portland’s working waterfront and is a favorite among locals and visitors alike.

A large crowd gathers outside The Porthole restaurant on a sunny day in Portland, Maine, with a red and blue sign reading "The Porthole, Portland Maine, Since 1929" and shipyard buildings and boats along the waterfront in the background.

🍺 Evening Brew: Shipyard Brewing Company

Next, head to Shipyard Brewing Company, located at 27 Hancock Street. As one of Maine’s most renowned breweries, Shipyard offers a rotating selection of 20 beers on tap, including seasonal and pilot brews. Their tasting room provides a cozy atmosphere to sample flagship favorites like Export Ale and the popular Pumpkinhead. Pair your pint with a slice from their delicious food menu, featuring pizzas and snacks.

A server brings a pizza to four people sitting at a wooden table, enjoying beer and food beneath a neon “Portland Shipyard Maine” sign in a cozy restaurant.

🚤 Sunset Escape: Ferry to Peaks Island

After enjoying Shipyard Brewing Company, take a leisurely ferry ride to Peaks Island. The ferry ride offers scenic views of Casco Bay and is a relaxing way to transition from the city’s hustle to island tranquility. The Inn on Peaks Island is a short walk from the ferry terminal and offers a charming setting for dinner

🍽️ Dinner Finale: The Inn on Peaks Island

Conclude your day with a delightful dinner at The Inn on Peaks Island. This island retreat offers a menu featuring fresh Maine seafood, crisp salads, and creative pub fare with a flair. Enjoy your meal while taking in views of Casco Bay. The Inn also serves Shipyard Brewing Company’s Capt’n Eli’s Soda and seasonal cask-conditioned ale brewed on-site.

Outdoor patio with metal tables and chairs under large blue "SHIPYARD" umbrellas. Two people enjoy a beer at a table, with views of the street, parked cars, trees, and water in Maine in the background.