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Ultimate 13-Day Portland, Maine and Windham Adventure Itinerary

Last updated: 2024 Jun 14

Coastal Charm and Culinary Delights

Morning

Start your day with a delightful breakfast at Black Mountain Burger Co., known for its local ingredients and cozy atmosphere. Afterward, embark on the Portland, Maine Local Brewery & Spirits Bus Tour to sample the best craft beverages in the area.

Afternoon

For lunch, savor the flavors of Maine at Sebago Brewing Company, a popular spot for both locals and visitors. Afterward, take a leisurely stroll through the historic Old Port district.

Evening

Conclude your day with a dinner at Faro Italian Grille, offering a fine dining experience with a modern twist on Italian cuisine.

Bedtime

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Lighthouses and Seafood

Morning

Enjoy a classic Maine breakfast at Pleasant Street Restaurant, a favorite among the locals. Then, set off on the Portland, Maine Coastal Lighthouses Guided Bicycle Tour to explore the iconic lighthouses of the region.

Afternoon

For lunch, indulge in a seafood feast on the Portland Old Port Seafood Lovers Tour, where you'll sample the best catches of the day. Afterward, take a relaxing Portland Schooner Tall Ship Cruise on Casco Bay.

Evening

In the evening, opt for a casual dinner at Black Mountain Burger Co., known for its creative burger combinations and laid-back vibe.

Bedtime

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Historic Treasures and Local Flavors

Morning

Start your day with a hearty breakfast at 92 Bank Cafe, a charming spot with a menu featuring local ingredients. Then, immerse yourself in the history of the city on the Portland, Maine 2-Hour Guided History Tour.

Afternoon

For lunch, try the authentic Italian cuisine at Faro Italian Grille, known for its handmade pasta and warm ambiance. Afterward, continue your exploration with the Portland, Maine City and Lighthouse E Bike Tour.

Evening

Enjoy a sophisticated dinner at Pleasant Street Restaurant, a fine dining establishment offering a seasonal menu inspired by the flavors of Maine.

Bedtime

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Culinary Adventure and Sunset Kayaking

Morning

Start your day with a leisurely breakfast at 92 Bank Cafe, known for its delicious pastries and artisanal coffee. Then, embark on the Portland Old Port Culinary Walking Tour to taste a variety of local specialties.

Afternoon

For a unique experience, enjoy a late lunch at Windham Junction Country Kitchen, a hidden gem known for its comfort food and welcoming atmosphere. Afterward, prepare for a magical evening on the Portland, Maine Sunset Kayak Tour with a Guide.

Evening

Conclude your day with a relaxed dinner at D's Pizza Pasta & Subs, a family-friendly pizzeria with a menu that caters to all tastes.

Bedtime

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