Portland, Maine

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:

• Start your day with breakfast at Local Sprouts Cooperative, which has a variety of gluten-free options on their menu.
• Visit the Children's Museum & Theatre of Maine, which has interactive exhibits and activities for kids.
• For lunch, head to Green Elephant Vegetarian Bistro, which has a separate gluten-free menu.
• Spend the afternoon at Deering Oaks Park, a large park with walking trails and a playground for kids.
• End your day with dinner at The Greenery Cafe, which offers gluten-free and vegan options.

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!