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4-Day Portland, Maine Adventure Itinerary

Last updated: 2024 Jun 14

Exploring Portland's History and Cuisine

Morning

Start your day with a hearty breakfast at Becky's Diner, a local favorite known for its classic American breakfast dishes. Afterward, head to Portland, Maine 2-Hour Guided History Tour to get an insightful overview of the city's rich history and landmarks.

Afternoon

For lunch, enjoy fresh seafood at J's Oyster, renowned for its oysters and waterfront views. Post-lunch, take a leisurely stroll along the Eastern Promenade, offering stunning views of Casco Bay and plenty of photo opportunities.

Evening

Dine at Fore Street, one of Portland's most acclaimed restaurants known for its farm-to-table cuisine. End your evening with a visit to Rising Tide Brewing Company to sample some local craft beers.

Bedtime

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Lighthouses and Local Flavors

Morning

Begin your day with breakfast at Hot Suppa, famous for its Southern-inspired dishes. Then embark on the Portland Best of Maine Lighthouse Scenic Cruise, where you'll explore some of Maine's iconic lighthouses from the water.

Afternoon

Have lunch at The Honey Paw, known for its creative Asian fusion cuisine. Afterward, join the Portland Old Port Culinary Walking Tour to taste various local delicacies while learning about the area's culinary history.

Evening

Enjoy dinner at Eventide Oyster Co., celebrated for its innovative seafood dishes. Conclude your day with a relaxing sunset cruise on Casco Bay by joining the Portland Sunset Lighthouse Cruise in Casco Bay with Drinks.

Bedtime

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Artisanal Adventures and Scenic Views

Morning

Kick off your morning with breakfast at The Green Elephant, offering delicious vegetarian options. Next, visit the historic Tate House Museum to delve into colonial-era architecture and history.

Afternoon

For lunch, head to Duckfat where you can savor their famous fries cooked in duck fat. In the afternoon, take part in the unique experience of visiting New England Distilling, where you can learn about traditional distilling methods and sample spirits.

Evening

Dine at Street & Co., known for its Mediterranean-inspired seafood dishes. Wrap up your evening by exploring Portland's vibrant arts scene or enjoying live music at one of the local venues.

Bedtime

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Outdoor Fun and Farewell Feast

Morning

Start your final day with breakfast at Petite Jacqueline, a charming French bistro offering delightful morning fare. Then embark on an adventurous tour with the Portland Trolley City Tour with Portland Head Light Stop, which includes a stop at one of Maine's most photographed lighthouses.

Afternoon

Lunch will be at Central Provisions, known for its small plates perfect for sharing. Spend your afternoon exploring more of Portland’s scenic beauty by taking part in the fun-filled activity of a self-guided scavenger hunt around town: Portland Scavenger Hunt.

Evening

Conclude your trip with dinner at DiMillo's On the Water Restaurant for an unforgettable dining experience on a converted ferry boat overlooking Casco Bay.

Bedtime

Find amazing hotels in Portland, Maine, USA.