5 Days Exploring Portland Maine Itinerary

Kick off your morning with breakfast at The Holy Donut, famous for its potato donuts. Then embark on the Portland Best of Maine Lighthouse Scenic Cruise, where you'll visit some of Maine's most iconic lighthouses.

Have lunch at Duckfat, known for its Belgian fries and sandwiches. In the afternoon, visit the popular Rising Tide Brewing Company to sample some local craft beers.

For dinner, make reservations at Central Provisions, offering small plates with big flavors. End your day with a fun and informative experience on the Portland Old Port Brewery & Pub Walking Tour.

Begin your day with breakfast at Becky's Diner, a local favorite for hearty meals. Then enjoy an active morning on the water with the Portland Private Charter on a Vintage Lobster Boat. This unique experience offers stunning views and an authentic taste of local culture.

After your boat tour, have lunch at J's Oyster for some classic New England fare. Spend your afternoon exploring the beautiful trails and vistas along the Eastern Promenade.

Dine at Street & Co. in Portland’s Old Port district for fresh seafood dishes. Conclude your evening by participating in the intriguing and educational Portland Crime & Injustice Guided Walking Tour.

Start your morning with coffee and pastries from Tandem Coffee + Bakery. Then take part in an insightful cultural experience by joining the guided tour at 10 AM:  Portland Black History Guided Walking Tour. This tour sheds light on important aspects of Portland's African American heritage.

Enjoy lunch at Flatbread Company which offers delicious wood-fired pizzas made from organic ingredients. Afterward, delve into more history by visiting Fort Gorges: Fort Gorges. The fort is accessible only by boat or kayak which adds an adventurous twist to this historical site.

Dinner awaits you at The Honey Paw, known for its inventive Asian fusion dishes. Cap off your night by enjoying a relaxing drink while watching sunset views during Portland Casco Bay Sunset and Lighthouse Cruise [595136].

Fuel up with breakfast from Arabica Coffee House before embarking on an exciting biking adventure around Portland’s peninsula: Portland Guided Bike Tour Around The Peninsula [388782]. It’s perfect way to see city while staying active.

For lunch stop by Gilbert’s Chowder House where you can savor hearty bowls clam chowder among other delights . Post-lunch visit New England Distilling:{ A-New England Distilling[21491]} learn about distillation process sample their spirits.

End trip memorable note having dinner renowned restaurant: { R-Scales } offering wide range seafood options . Finish last evening enjoying live music vibrant atmosphere one many bars found throughout city.