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Portland, Maine

5 day itinerary for Portland, Maine

Personalized with:

Make it family friendly

Make it pet friendly

Include gluten free food options

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Itinerary

Here's a 5-day itinerary for Portland, Maine that is family-friendly, pet-friendly, and includes gluten-free food options:

Day 1:

  • Start your day with breakfast at The Holy Donut, which offers gluten-free donuts made with potato flour.
  • Take a walk around the Eastern Promenade, a beautiful park overlooking Casco Bay. It's a great place to let your furry friend stretch their legs.
  • For lunch, head to Silly's Restaurant, which has a wide variety of gluten-free options on their menu.
  • Spend the afternoon exploring the Portland Museum of Art, which has a collection of over 18,000 works of art.
  • End your day with dinner at Flatbread Company, which offers gluten-free pizza options.

Day 2:

  • Start your day with breakfast at Becky's Diner, a classic diner that offers gluten-free pancakes and toast.
  • Take a scenic drive out to Cape Elizabeth and visit the Portland Head Light, one of the most photographed lighthouses in the country.
  • For lunch, stop by Bite Into Maine, a food truck that serves gluten-free lobster rolls.
  • Spend the afternoon at Willard Beach, a dog-friendly beach where your furry friend can play in the sand and water.
  • End your day with dinner at Street & Co., which offers gluten-free seafood options.

Day 3:

Day 4:

  • Start your day with breakfast at Tandem Coffee + Bakery, which has gluten-free pastries and bread.
  • Take a ferry to Peaks Island, where you can explore the island on foot or by bike. Dogs are allowed on the ferry and on the island.
  • For lunch, stop by The Cockeyed Gull, which has gluten-free options on their menu.
  • Spend the afternoon at Back Cove Trail, a scenic walking trail that offers views of the Portland skyline.
  • End your day with dinner at Local 188, which has gluten-free options on their menu.

Day 5:

  • Start your day with breakfast at Hot Suppa, which has gluten-free pancakes and toast.
  • Visit the Portland Observatory, a historic tower that offers panoramic views of the city.
  • For lunch, head to Otto Pizza, which offers gluten-free pizza options.
  • Spend the afternoon at Fort Williams Park, a large park with walking trails and a beach.
  • End your day with dinner at Duckfat, which has gluten-free options on their menu.

I hope this itinerary helps you plan your trip to Portland, Maine!

Places of interest

The Holy Donut Portland, Maine

The Holy Donut

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Eastern Promenade Portland, Maine

Eastern Promenade

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Silly's Restaurant Portland, Maine

Silly's Restaurant

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Portland Museum of Art Portland, Maine

Portland Museum of Art

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Flatbread Company Portland, Maine

Flatbread Company

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Becky's Diner Portland, Maine

Becky's Diner

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Portland Head Light Portland, Maine

Portland Head Light

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Bite Into Maine Portland, Maine

Bite Into Maine

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Willard Beach Portland, Maine

Willard Beach

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Street & Co. Portland, Maine

Street & Co.

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Local Sprouts Cooperative Portland, Maine

Local Sprouts Cooperative

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Children's Museum & Theatre of Maine Portland, Maine

Children's Museum & Theatre of Maine

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Green Elephant Vegetarian Bistro Portland, Maine

Green Elephant Vegetarian Bistro

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Deering Oaks Park Portland, Maine

Deering Oaks Park

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The Greenery Cafe Portland, Maine

The Greenery Cafe

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Tandem Coffee + Bakery Portland, Maine

Tandem Coffee + Bakery

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Peaks Island Portland, Maine

Peaks Island

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The Cockeyed Gull Portland, Maine

The Cockeyed Gull

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Back Cove Trail Portland, Maine

Back Cove Trail

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Local 188 Portland, Maine

Local 188

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Hot Suppa Portland, Maine

Hot Suppa

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Portland Observatory Portland, Maine

Portland Observatory

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Otto Pizza Portland, Maine

Otto Pizza

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Fort Williams Park Portland, Maine

Fort Williams Park

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Duckfat Portland, Maine

Duckfat

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