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5-day trip to Portland, Maine Itinerary

Last updated: 2024 Jun 14

Exploring Portland's Landmarks

Morning

Start your day by visiting the iconic Portland Head Light, one of the most photographed lighthouses in the United States. Afterward, grab a delicious breakfast at Duckfat and indulge in their famous Belgian-style fries.

Afternoon

Take a scenic cruise on Portland Schooner Tall Ship Cruise on Casco Bay and enjoy breathtaking views of Casco Bay. For lunch, head to Eventide Oyster Co. and savor their fresh seafood dishes.

Evening

Immerse yourself in Portland's history with the Portland, Maine Hidden Histories Guided Walking Tour. Afterward, treat yourself to a delightful dinner at Fore Street, known for its farm-to-table cuisine.

Bedtime

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4.79
Portland Head Light
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4.54
Portland Schooner Tall Ship Cruise on Casco Bay
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Culinary Delights in Portland

Morning

Start your day with a visit to Eastern Promenade, a beautiful waterfront park. Grab a coffee and pastry at The Honey Paw before exploring the park's trails.

Afternoon

Embark on the Portland Old Port Culinary Walking Tour and sample a variety of local delicacies. For lunch, enjoy the vibrant atmosphere and delicious food at Central Provisions.

Evening

Experience Portland's thriving craft beer scene with the Portland, Maine Local Brewery & Spirits Bus Tour. Indulge in dinner at Street & Co., known for its seafood dishes.

Bedtime

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4.53
Eastern Promenade
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4.81
Portland Old Port Culinary Walking Tour
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Historical and Cultural Exploration

Morning

Explore the fascinating history of Portland with the Portland, Maine 2-Hour Guided History Tour. Grab a quick breakfast at Little Giant before the tour.

Afternoon

Visit the Tate House Museum, a historic colonial home, and learn about Portland's past. For lunch, head to The Front Room Restaurant & Bar and enjoy their delicious American cuisine.

Evening

Immerse yourself in the local art scene with a visit to the Portland Museum of Art. Afterward, have dinner at Boda, a popular Thai restaurant in the city.

Bedtime

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4.86
Portland, Maine 2-Hour Guided History Tour
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Tate House Museum
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Outdoor Adventures and Shopping

Morning

Start your day with a hike at Fort Gorges, a historic fort located on an island in Casco Bay. Grab a quick breakfast at Nosh Kitchen Bar before heading out.

Afternoon

Explore the charming coastal town of Cape Elizabeth and visit Kittery Premium Outlets for some shopping. For lunch, enjoy a delicious meal at The Highroller Lobster Co..

Evening

Take a relaxing sunset cruise on Portland Sunset Lighthouse Cruise in Casco Bay with Drinks and enjoy the scenic beauty of the coastline. End the day with dinner at Scales Restaurant, known for its seafood specialties.

Bedtime

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4.73
Fort Gorges
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4.29
Kittery Premium Outlets
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Local Experiences and Distillery Tour

Morning

Start your day with a self-guided tour of Portland's vibrant downtown using the Portland Exploration Self-Guided Driving & Walking Tour. Grab a coffee at Tandem Coffee + Bakery to fuel your exploration.

Afternoon

Discover the art of distilling at New England Distilling with a guided tour and tasting. For lunch, head to Bruno's and enjoy their delicious Italian cuisine.

Evening

End your trip with a visit to Rising Tide Brewing Company and savor their craft beers. For dinner, indulge in a delightful meal at Hugo's, known for its innovative and creative dishes.

Bedtime

Find amazing hotels in Portland, Maine.