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4-Day Adventure in Portland, Maine Itinerary

Last updated: 2024 Jun 14

Exploring Portland's Waterfront and History

Morning

Start your day with a hearty breakfast at Becky's Diner, a local favorite known for its classic American breakfast and friendly atmosphere. Then head to Portland, Maine 2-Hour Guided History Tour to dive into the rich history of Portland. This tour will give you an excellent overview of the city's past and significant landmarks.

Afternoon

For lunch, visit Eventide Oyster Co. to enjoy some of the best oysters in town. Afterward, take a stroll along the Eastern Promenade, a beautiful park offering stunning views of Casco Bay and plenty of walking trails.

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 along the waterfront or explore some local shops in Old Port.

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 Culinary Delights

Morning

Begin your morning with coffee and pastries at Tandem Coffee and Bakery. Then embark on the Portland Best of Maine Lighthouse Scenic Cruise, where you'll see some of Maine's most iconic lighthouses from the water.

Afternoon

Have lunch at The Highroller Lobster Co., famous for its creative lobster rolls. Afterward, join the Portland Old Port Culinary Walking Tour to sample various local delicacies while learning about Portland's culinary scene.

Evening

Dine at Street & Co., known for its seafood dishes and cozy atmosphere. If you're up for it, enjoy a nightcap at one of Old Port's many bars or lounges.

Bedtime

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4.86
Portland Best of Maine Lighthouse Scenic Cruise
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4.81
Portland Old Port Culinary Walking Tour
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Artisanal Brews and Scenic Views

Morning

Kick off your day with breakfast at Hot Suppa!, offering Southern-inspired dishes made from locally sourced ingredients. Then take part in the Portland Trolley City Tour with Portland Head Light Stop to explore more of Portland's landmarks including a stop at the famous lighthouse.

Afternoon

Lunch will be at Duckfat, where you can indulge in their famous fries cooked in duck fat. Post-lunch, visit Rising Tide Brewing Company for a brewery tour and tasting session.

Evening

For dinner, head to The Honey Paw which offers unique Asian-inspired dishes. Finish your evening with a leisurely walk around downtown or perhaps catch some live music.

Bedtime

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4.82
Portland Trolley City Tour with Portland Head Light Stop
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Rising Tide Brewing Company
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Outdoor Adventures and Local Flavors

Morning

Start your morning with breakfast from The Green Elephant, known for its vegetarian cuisine that even meat-eaters love. Then go on an adventure with the Portland Private Charter on a Vintage Lobster Boat, offering an intimate experience on Casco Bay.

Afternoon

Enjoy lunch at Central Provisions, which serves small plates perfect for sharing. Afterward, take part in the unique experience offered by the New England Distilling, where you can learn about distillation processes and sample some spirits.

Evening

Conclude your day with dinner at Scales, featuring fresh seafood right on the waterfront. End your night by exploring more of Old Port or simply relaxing by Casco Bay.

Bedtime

Find amazing hotels in Portland, Maine.