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Portland Maine

4 day itinerary for Portland Maine

Personalized with:

Older teenagers

Lobster

Coast

Have rental car

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Itinerary

Here's a suggested itinerary for 4 days in Portland, Maine:

Day 1:

  • Start your day with a visit to the Portland Head Light, one of the most photographed lighthouses in the country. It's located in Cape Elizabeth, just a short drive from Portland.
  • After taking in the views, head back to Portland and grab lunch at Eventide Oyster Co. This restaurant is known for its amazing lobster rolls and fresh oysters.
  • Spend the afternoon exploring the Old Port, a historic district filled with shops, galleries, and restaurants. You can also take a walk along the waterfront and enjoy the views of Casco Bay.
  • For dinner, head to Street & Co., a cozy seafood restaurant that serves up delicious lobster dishes.

Day 2:

  • Start your day with a scenic drive up the coast to Acadia National Park. It's about a 3-hour drive from Portland, but the views along the way are worth it.
  • Spend the day hiking, biking, or kayaking in the park. There are plenty of trails and activities to choose from, so you can tailor your day to your interests.
  • For dinner, head back to Portland and try out The Highroller Lobster Co. This food truck turned restaurant serves up some of the best lobster rolls in town.

Day 3:

  • Start your day with a visit to the Portland Museum of Art. This museum has a great collection of American and European art, as well as contemporary works by Maine artists.
  • After the museum, head to the Eastern Promenade, a park that offers stunning views of Casco Bay. You can take a walk along the waterfront or have a picnic in the park.
  • For lunch, head to J's Oyster, a local institution that's been serving up fresh seafood since 1979.
  • In the afternoon, take a drive out to the Portland Head Light again and explore the nearby Fort Williams Park. This park has walking trails, picnic areas, and historic military buildings.
  • For dinner, head to Scales, a seafood restaurant that's known for its lobster dishes and waterfront views.

Day 4:

  • Start your day with a visit to the Maine Maritime Museum in Bath. It's about an hour's drive from Portland, but it's worth it to learn about Maine's maritime history.
  • After the museum, head to Reid State Park, a beautiful beach that's perfect for swimming, sunbathing, and exploring the rocky coastline.
  • For lunch, head to The Lobster Shack at Two Lights, a casual seafood restaurant that's located right on the water.
  • In the afternoon, take a drive along the scenic Route 1 and explore some of the small coastal towns along the way. You can stop for ice cream, visit local shops, or just enjoy the views.
  • For dinner, head back to Portland and try out Fore Street, a farm-to-table restaurant that's known for its wood-fired cooking and fresh seafood.

Places of interest

Portland Head Light Portland Maine

Portland Head Light

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Eventide Oyster Co. Portland Maine

Eventide Oyster Co.

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Old Port Portland Maine

Old Port

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Street & Co. Portland Maine

Street & Co.

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Acadia National Park Portland Maine

Acadia National Park

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The Highroller Lobster Co. Portland Maine

The Highroller Lobster Co.

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Portland Museum of Art Portland Maine

Portland Museum of Art

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Eastern Promenade Portland Maine

Eastern Promenade

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J's Oyster Portland Maine

J's Oyster

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Fort Williams Park Portland Maine

Fort Williams Park

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Scales Portland Maine

Scales

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Maine Maritime Museum Portland Maine

Maine Maritime Museum

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Reid State Park Portland Maine

Reid State Park

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The Lobster Shack at Two Lights Portland Maine

The Lobster Shack at Two Lights

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Route 1 (scenic drive) Portland Maine

Route 1 (scenic drive)

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Fore Street Portland Maine

Fore Street

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