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Travel AI

Portland Maine Adventure 7 Days Itinerary

Last updated: 2024 Jun 14

Exploring the Old Port

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, embark on the Portland, Maine 2-Hour Guided History Tour to get an in-depth understanding of Portland's rich history and vibrant culture.

Afternoon

Head to Eventide Oyster Co. for lunch, where you can enjoy fresh oysters and other seafood delicacies. Post-lunch, take a leisurely stroll along the Eastern Promenade, offering stunning views of Casco Bay and plenty of photo opportunities.

Evening

For dinner, visit Fore Street, renowned for its farm-to-table cuisine and rustic ambiance. End your evening with a relaxing walk around the Old Port district, soaking in the lively atmosphere.

Bedtime

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4.86
Portland, Maine 2-Hour Guided History Tour
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4.53
Eastern Promenade
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Lighthouses and Lobster Boats

Morning

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

Afternoon

Enjoy lunch at The Honey Paw, known for its creative Asian fusion dishes. In the afternoon, explore Fort Gorges by taking the Fort Gorges tour; this historic fort offers a unique glimpse into Portland's military past.

Evening

Dine at DiMillo's On the Water, a floating restaurant offering delicious seafood with beautiful waterfront views. Cap off your night with drinks at one of Portland's many cozy bars or lounges.

Bedtime

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4.86
Portland Best of Maine Lighthouse Scenic Cruise
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4.73
Fort Gorges
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Brews and Views

Morning

Kick off your morning with breakfast at The Green Elephant, which offers delightful vegetarian options. Afterward, join the Portland Trolley City Tour with Portland Head Light Stop to see more of Portland's landmarks including the famous Portland Head Light.

Afternoon

Have lunch at Duckfat, where you can indulge in their famous fries cooked in duck fat. Spend your afternoon visiting local breweries on the Portland Old Port Brewery & Pub Walking Tour, sampling some of Portland’s best craft beers.

Evening

For dinner, make reservations at Street & Co., known for its exceptional seafood dishes. End your evening by exploring more of Old Port’s nightlife or taking a peaceful evening walk along Commercial Street.

Bedtime

Find amazing hotels in Portland, Maine.

4.82
Portland Trolley City Tour with Portland Head Light Stop
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4.78
Portland Old Port Brewery & Pub Walking Tour
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Culinary Delights and Coastal Sights

Morning

Start your day with breakfast at Central Provisions, offering an array of small plates perfect for sharing. Then embark on the fascinating Portland Food Walking Tour with Tastings, where you'll sample some of Portland’s best culinary offerings while learning about its food history.

Afternoon

For lunch, visit Boda to enjoy Thai street food-inspired dishes in a chic setting. In the afternoon, take part in the scenic Portland Schooner Tall Ship Cruise on Casco Bay, which provides breathtaking views of Casco Bay from an authentic schooner.

Evening

Dine at Scales for an upscale seafood experience right on the waterfront. Conclude your day by enjoying some live music or theater performances in downtown Portland.

Bedtime

Find amazing hotels in Portland, Maine.

Portland Food Walking Tour with Tastings
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4.54
Portland Schooner Tall Ship Cruise on Casco Bay
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Historic Homes and Scenic Cruises

Morning

Begin your day with breakfast at Becky's Diner, a beloved local spot known for its hearty meals and friendly service. Afterward, visit the Tate House Museum, an 18th-century home that offers a fascinating glimpse into Portland's colonial past.

Afternoon

For lunch, head to Portland Lobster Company to enjoy fresh lobster rolls and other seafood delights right by the water. In the afternoon, embark on the Portland Best of Maine Lighthouse Scenic Cruise, which provides stunning views of Maine's iconic lighthouses from the sea.

Evening

Dine at Street & Co., renowned for its exceptional seafood dishes in a cozy setting. End your evening with a leisurely stroll through the Old Port district, soaking in the vibrant nightlife.

Bedtime

Find amazing hotels in Portland, Maine.

Tate House Museum
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4.86
Portland Best of Maine Lighthouse Scenic Cruise
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Art and Culture Extravaganza

Morning

The Green Elephant is perfect for a vegetarian breakfast to start your day on a healthy note. Then head to the Portland Museum of Art to explore its impressive collection of American and European art.

Afternoon

Empire Chinese Kitchen is an excellent choice for lunch with its delicious dim sum offerings. Spend your afternoon on the Portland Old Port Culinary Walking Tour, where you'll sample some of Portland’s best culinary offerings while learning about its food history.

Evening

Scales offers an upscale dining experience with fresh seafood right on the waterfront. Conclude your day by enjoying some live music or theater performances in downtown Portland.

Bedtime

Find amazing hotels in Portland, Maine.

4.81
Portland Old Port Culinary Walking Tour
Book Now

Nature and Farewell Feasts

Morning

Hot Suppa is ideal for a Southern-inspired breakfast to kickstart your final day. Then take part in the Portland Coastal Lighthouses Guided Bicycle Tour for an active morning exploring some of Maine's most picturesque lighthouses.

Afternoon

Duckfat is perfect for lunch with their famous fries cooked in duck fat. Spend your afternoon visiting local breweries on the Portland Old Port Brewery & Pub Walking Tour, sampling some of Portland’s best craft beers.

Evening

Bedtime

Find amazing hotels in Portland, Maine.