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3 Days of Adventure in Portland, Maine Itinerary

Last updated: 2024 Jun 14

Exploring Portland's Historic Charm

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's rich history and iconic landmarks. This guided tour is perfect for first-time visitors as it covers all the must-see spots.

Afternoon

For lunch, visit Eventide Oyster Co. and indulge in their famous brown butter lobster roll. Post-lunch, take a leisurely stroll along the Eastern Promenade, a scenic park offering stunning views of Casco Bay and plenty of photo opportunities.

Evening

In the evening, enjoy dinner at Fore Street, renowned for its farm-to-table cuisine and rustic ambiance. End your day with a relaxing walk through the Old Port district, exploring its charming cobblestone streets and boutique shops.

Bedtime

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4.82
Portland Trolley City Tour with Portland Head Light Stop
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4.53
Eastern Promenade
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Cultural Immersion and Culinary Delights

Morning

Begin your morning with a visit to Tate House Museum, where you can explore one of the oldest surviving buildings in Portland and learn about colonial life in New England. For breakfast or brunch, head to Hot Suppa, known for its Southern-inspired dishes and cozy atmosphere.

Afternoon

After brunch, embark on the Portland Food Walking Tour with Tastings. This tour will take you through some of Portland's best eateries while providing insights into the city's culinary scene. It's an excellent way to sample local flavors.

Evening

For dinner, make your way to Duckfat, famous for its Belgian fries and poutine. If you're up for some nightlife afterward, visit Rising Tide Brewing Company to enjoy some locally brewed craft beers in a lively setting.

Bedtime

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Tate House Museum
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Portland Food Walking Tour with Tastings
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Outdoor Adventures and Scenic Views

Morning

Kick off your day with breakfast at The Honey Paw, offering unique Asian-inspired dishes that are sure to delight your taste buds. Then head out on the Portland Best of Maine Lighthouse Scenic Cruise, which offers breathtaking views of Maine's iconic lighthouses from the water.

Afternoon

For lunch, stop by Central Provisions for their innovative small plates that are perfect for sharing. In the afternoon, rent bikes from Maine Coast Bicycle Rentals and explore more of Portland's scenic coastline at your own pace.

Evening

Conclude your trip with dinner at DiMillo's On the Water, where you can enjoy fresh seafood while taking in beautiful waterfront views. If time permits after dinner, consider taking part in the relaxing Portland Sunset Lighthouse Cruise in Casco Bay with Drinks.

Bedtime

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