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10 Days in Portland, Maine: Food, Nature, History Itinerary
Last updated: 2024 Jun 14Welcome to Portland!
Morning
Start your day with a hearty breakfast at Becky's Diner, a local favorite known for its classic American breakfast and friendly atmosphere. Afterward, head to Portland Trolley City Tour with Portland Head Light Stop to get an overview of the city and its history. This tour will take you around the key sights of Portland including the iconic Portland Head Light.
Afternoon
For lunch, visit Eventide Oyster Co. for some of the best oysters in town. Post-lunch, enjoy a leisurely stroll along the Eastern Promenade, a scenic park offering stunning views of Casco Bay and plenty of spots to relax.
Evening
End your day with dinner at Fore Street, one of Portland's most celebrated restaurants known for its farm-to-table cuisine and rustic ambiance.
Bedtime
Find amazing hotels in Portland, Maine.
4.82Portland Trolley City Tour with Portland Head Light Stop
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4.82Portland Trolley City Tour with Portland Head Light Stop
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4.53Eastern Promenade
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4.53Eastern Promenade
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Exploring History and Breweries
Morning
Begin your day with breakfast at Hot Suppa, famous for its Southern-inspired dishes. Then head over to the Tate House Museum to delve into Portland's colonial history.
Afternoon
For lunch, try Duckfat, renowned for its delicious fries and sandwiches. In the afternoon, visit Rising Tide Brewing Company to sample some local craft beers and learn about the brewing process.
Evening
Have dinner at Street & Co., a seafood restaurant known for its fresh catches and cozy atmosphere.
Bedtime
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Tate House Museum
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Tate House Museum
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Rising Tide Brewing Company
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Rising Tide Brewing Company
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Lighthouses and Culinary Delights
Morning
Start your morning with breakfast at The Green Elephant, offering delightful vegetarian options. Then embark on the Portland Best of Maine Lighthouse Scenic Cruise, which will take you around several picturesque lighthouses along the coast.
Afternoon
Enjoy lunch at The Honey Paw, known for its creative Asian fusion dishes. Afterward, join the Portland Old Port Culinary Walking Tour to explore some of Portland's best food spots while learning about its culinary history.
Evening
Dine at Scales, an upscale seafood restaurant located on the waterfront.
Bedtime
Find amazing hotels in Portland, Maine.
4.86Portland Best of Maine Lighthouse Scenic Cruise
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4.86Portland Best of Maine Lighthouse Scenic Cruise
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4.81Portland Old Port Culinary Walking Tour
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4.81Portland Old Port Culinary Walking Tour
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Nature and Relaxation Day
Morning
Kick off your day with breakfast at Becky's Diner again for another round of their delicious offerings. Then go on a relaxing adventure with the Portland Private Charter on a Vintage Lobster Boat, where you can enjoy beautiful views of Casco Bay while learning about lobster fishing.
Afternoon
For lunch, head over to Central Provisions for an eclectic menu that changes seasonally. Spend your afternoon exploring nature by renting bikes from Maine Coast Bicycle Rentals and riding along scenic coastal paths.
Evening
Finish your day with dinner at DiMillo's On the Water, a unique dining experience aboard a converted ferry boat offering stunning harbor views.
Bedtime
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5.00Portland Private Charter on a Vintage Lobster Boat
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5.00Portland Private Charter on a Vintage Lobster Boat
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Maine Coast Bicycle Rentals
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Maine Coast Bicycle Rentals
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Historical Tours and Sunset Cruises
Morning
Start your day with breakfast at Becky's Diner, known for its hearty meals and local charm. Afterward, dive into Portland's rich history with the Portland, Maine 2-Hour Guided History Tour, which will give you an in-depth look at the city's past.
Afternoon
For lunch, visit J's Oyster to enjoy some fresh seafood. Post-lunch, take a leisurely walk around the Old Port area and then join the Portland Old Port Seafood Lovers Tour to sample some of the best seafood dishes in town.
Evening
End your day with a serene experience on the Portland Sunset Lighthouse Cruise in Casco Bay with Drinks, where you can enjoy stunning views of the sunset over Casco Bay while sipping on a drink.
Bedtime
Find amazing hotels in Portland, Maine.
4.86Portland, Maine 2-Hour Guided History Tour
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4.86Portland, Maine 2-Hour Guided History Tour
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4.71Portland Old Port Seafood Lovers Tour
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4.71Portland Old Port Seafood Lovers Tour
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Art and Culture Day
Morning
Begin your day with breakfast at Hot Suppa, known for its Southern-inspired breakfast dishes. Then head to the Portland Museum of Art to explore its impressive collection of American and European art.
Afternoon
For lunch, try The Honey Paw for their creative Asian fusion dishes. In the afternoon, take part in the Portland Maine Lighthouses Sightseeing Cruise with Drinks to see some of Maine's most iconic lighthouses from a unique perspective.
Evening
Have dinner at Flatbread Company, famous for its wood-fired pizzas made with organic ingredients.
Bedtime
Find amazing hotels in Portland, Maine.
4.30Portland Maine Lighthouses Sightseeing Cruise with Drinks
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4.30Portland Maine Lighthouses Sightseeing Cruise with Drinks
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Outdoor Adventures and Brewery Tours
Morning
Start your morning with breakfast at The Green Elephant, offering delightful vegetarian options. Then embark on an outdoor adventure with the Portland, Maine Coastal Lighthouses Guided Bicycle Tour, which will take you along scenic coastal paths and past several beautiful lighthouses.
Afternoon
Enjoy lunch at Duckfat, renowned for its delicious fries and sandwiches. Afterward, join the Portland Old Port Brewery & Pub Walking Tour to sample some local brews while learning about Portland's brewing history.
Evening
Dine at Boda, a Thai restaurant known for its innovative dishes and cozy atmosphere.
Bedtime
Find amazing hotels in Portland, Maine.
5.00Portland, Maine Coastal Lighthouses Guided Bicycle Tour
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5.00Portland, Maine Coastal Lighthouses Guided Bicycle Tour
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4.78Portland Old Port Brewery & Pub Walking Tour
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4.78Portland Old Port Brewery & Pub Walking Tour
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Scenic Drives and Local Flavors
Morning
Kick off your day with breakfast at Becky's Diner once more for another round of their delicious offerings. Then go on a scenic drive with the Portland Self-Guided Sightseeing Driving Audio Tour, which will take you through some of Portland's most picturesque areas.
Afternoon
For lunch, head over to Central Provisions for an eclectic menu that changes seasonally. Spend your afternoon exploring more local flavors by joining the Portland Food Walking Tour with Tastings.
Evening
Finish your day with dinner at DiMillo's On the Water, offering stunning harbor views aboard a converted ferry boat.
Bedtime
Find amazing hotels in Portland, Maine.
4.13Portland Self-Guided Sightseeing Driving Audio Tour
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4.13Portland Self-Guided Sightseeing Driving Audio Tour
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Portland Food Walking Tour with Tastings
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Portland Food Walking Tour with Tastings
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Adventure and Relaxation
Morning
Start your day with breakfast at Hot Suppa, known for its Southern-inspired breakfast dishes. Then head out for an adventurous morning with the Portland, Maine City and Lighthouse E Bike Tour, which will take you through some of Portland's most scenic areas and iconic lighthouses.
Afternoon
For lunch, visit The Honey Paw to enjoy their creative Asian fusion dishes. Afterward, spend a relaxing afternoon at the New England Distilling, where you can learn about the distillation process and sample some locally crafted spirits.
Evening
End your day with dinner at Scales, an upscale seafood restaurant located on the waterfront.
Bedtime
Find amazing hotels in Portland, Maine.
Portland, Maine City and Lighthouse E Bike Tour
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Portland, Maine City and Lighthouse E Bike Tour
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New England Distilling
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New England Distilling
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Farewell Portland
Morning
Begin your final day with breakfast at Becky's Diner to enjoy one last hearty meal. Then take a peaceful walk along the Eastern Promenade to soak in the beautiful views of Casco Bay.
Afternoon
Portland Schooner Tall Ship Cruise on Casco Bay is a perfect way to spend your afternoon, sailing on a historic schooner while enjoying the scenic beauty of Casco Bay. For lunch, try Duckfat for their renowned fries and sandwiches.
Evening
Portland Sunset Lighthouse Cruise in Casco Bay with Drinks offers a serene end to your trip as you watch the sunset over Casco Bay while sipping on a drink. For dinner, visit DiMillo's On the Water for one last meal aboard this unique floating restaurant.
Bedtime
Find amazing hotels in Portland, Maine.
4.53Eastern Promenade
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4.53Eastern Promenade
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4.54Portland Schooner Tall Ship Cruise on Casco Bay
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4.54Portland Schooner Tall Ship Cruise on Casco Bay
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