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5 Days in Portland Maine

5 Days in Portland Maine Itinerary

Last updated: 2024 Jun 14

Exploring Portland's History

Morning
Start your day with a hearty breakfast at Hot Suppa, known for its Southern-inspired dishes. After breakfast, dive into the rich history of Portland with the Portland, Maine 2-Hour Guided History Tour. This tour will give you a comprehensive overview of the city's past.
Afternoon
For lunch, head to Eventide Oyster Co. to enjoy some fresh seafood. Afterward, visit the Tate House Museum, an 18th-century home that offers a glimpse into colonial life in Maine.
Evening
Dine at Fore Street, a farm-to-table restaurant offering delicious local cuisine. End your day with a relaxing evening on the water with the Portland Sunset Lighthouse Cruise in Casco Bay with Drinks. The cruise offers stunning views of the coastline and lighthouses.
Bedtime
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Outdoor Adventures and Local Brews

Morning
Begin your day with breakfast at The Holy Donut, famous for its potato donuts. Then embark on an exciting adventure with the Portland, Maine Coastal Lighthouses Guided Bicycle Tour. This tour will take you to some of the most iconic lighthouses along the coast.
Afternoon
For lunch, visit Duckfat, known for its Belgian fries and paninis. Afterward, explore local spirits at New England Distilling, where you can learn about and taste their handcrafted spirits.
Evening
Enjoy dinner at Central Provisions, offering small plates inspired by global flavors. Conclude your evening with a visit to Rising Tide Brewing Company for some locally brewed craft beer.
Bedtime
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Cultural Insights and Scenic Views

Morning
Have breakfast at Becky's Diner, a local favorite for classic American breakfasts. Then take part in the fascinating 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 J's Oyster, known for its fresh seafood dishes. Post-lunch, enjoy a leisurely walk along the scenic Eastern Promenade, offering beautiful views of Casco Bay.
Evening
Dine at Street & Co., renowned for its seafood pasta dishes. End your night by exploring Portland's darker side with the intriguing Portland, Maine Crime & Injustice Guided Walking Tour.
Bedtime
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Unique Tours and Local Flavors

Morning
Start your morning with breakfast at Arabica Coffee House before embarking on an insightful journey through African American history on the Portland, Maine Black History Guided Walking Tour. This tour provides valuable context about Portland's diverse heritage.
Afternoon
Have lunch at The Honey Paw, known for its Asian-inspired dishes. Afterward, experience Portland's vibrant food scene firsthand on the delightful Portland Food Walking Tour with Tastings. You'll get to sample various local delicacies while learning about their origins.
Evening
Dinner awaits you at Scales Restaurant, which specializes in fresh seafood dishes. Cap off your evening by enjoying some live music and drinks at one of Portland’s popular bars like The Thirsty Pig.
Bedtime
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Final Day Highlights

Morning
Begin your last day in Portland with breakfast from Tandem Coffee Roasters before setting out on an adventurous note by taking part in the unique experience offered by the  Portland Private Charter on a Vintage Lobster Boat. Enjoy breathtaking views while learning about lobster fishing traditions.
Afternoon
For lunch head over to Gilbert’s Chowder House to savor their famous chowders followed by exploring more historical insights via Downtown Portland In-App Audio Tour (ENG) at your own pace through this self-guided audio tour providing flexibility as well as detailed information about key landmarks around downtown area .
Evening
Conclude this memorable trip dining out elegantly within warm ambiance provided exclusively through { R-Five Fifty-Five } famous not only due impeccable service but also mouth-watering culinary delights making sure it leaves lasting impression forever cherished long after departure from beautiful city called simply 'PORTLAND'
Bedtime
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