5-Day Ultimate Portland, Maine Adventure Itinerary

Day 1: Exploring Portland

Portland, Maine

8:00AM

Breakfast at Becky's Diner

Kickstart your Portland adventure with a hearty breakfast at Becky's Diner, a local favorite known for its fresh seafood omelets and homemade pancakes.
Located near the waterfront for easy access to other attractions after breakfast.
USD15, 1 hour

9:30AM

Visit the Portland Head Light

Drive to Cape Elizabeth to see Maine's most iconic lighthouse, Portland Head Light, set against stunning coastal views.
It's about a 15-minute drive from the diner.
Free, 1 hour

11:00AM

Explore Fort Williams Park

Stroll around the beautiful Fort Williams Park next to the lighthouse for breathtaking seaside views and interesting historical sites.
Walk to nearby paths in the park.
Free, 2 hours

1:00PM

Lunch at Eventide Oyster Co.

Enjoy fresh oysters and unique lobster rolls at this trendy seafood spot that showcases the flavors of the sea.
Head back to downtown Portland, a 15-minute drive away.
USD30, 1.5 hours

3:00PM

Explore the Old Port District

Wander through the charming cobblestone streets of the Old Port, filled with boutique shops, galleries, and waterfront views.
Walking distance from Eventide Oyster Co.
Free, 3 hours

6:00PM

Dinner at Fore Street

Experience exquisite farm-to-table dining at this renowned restaurant known for its local ingredients and wood-fired dishes.
A short walk from the Old Port area.
USD50, 2 hours

8:30PM

Evening at the Portland Museum of Art

End your day with a visit to the Portland Museum of Art, showcasing impressive collections of American and European art.
Just a 5-minute drive or 15-minute walk from Fore Street.
USD15, 1.5 hours
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Day 2: Day Trip to Freeport

Freeport, Maine

8:00AM

Breakfast at the Standard Baking Co.

Start your day with fresh pastries and artisan coffee at this cozy bakery known for its locally-sourced ingredients.
Head back towards Old Port to reach the bakery, about a 10-minute drive.
USD10, 1 hour

9:30AM

Drive to Freeport

Embark on a scenic 20-minute drive to Freeport, the famous home of L.L. Bean and various outlet stores.
Follow I-295 N towards Freeport.
Free, 20 minutes

10:00AM

Shopping at L.L. Bean

Peruse the flagship L.L. Bean store and explore outdoor gear and apparel, perfect for adventures ahead.
Parking available at the L.L. Bean store.
Free, 1.5 hours

12:00PM

Lunch at Azure Café

Savor fresh salads and seafood dishes at this charming café with a welcoming atmosphere.
Located nearby within walking distance.
USD25, 1.5 hours

2:00PM

Visit the Freeport Historical Society

Learn about the history and culture of Freeport through intriguing exhibits and guided tours.
Just a 5-minute walk from Azure Café.
USD5, 1 hour

3:30PM

Explore Wolfe's Neck Woods State Park

Stroll through scenic trails at Wolfe's Neck Woods State Park while enjoying breathtaking views of Casco Bay.
10-minute drive from the Historical Society.
USD4, 2 hours

6:00PM

Dinner at The Lobster Cooker

Indulge in Maine’s famous lobster rolls and fresh seafood in a laid-back environment.
Return to Freeport town center, a short drive.
USD25, 1.5 hours

8:00PM

Drive Back to Portland

Wrap up your day with a relaxing drive back to Portland after a fun day in Freeport.
Follow the same route back to Portland.
Free, 20 minutes
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Day 3: Kennebunkport Excursion

Kennebunkport, Maine

8:00AM

Breakfast at The White Barn Inn

Begin your day with a luxurious breakfast at the beautifully appointed White Barn Inn, offering a delightful and elegant dining experience.
Travel approximately 30 minutes from Portland.
USD40, 1 hour

9:30AM

Walk the Kennebunk River Park

Explore the serene trails along the Kennebunk River and take in the natural beauty surrounding you.
This is a short walk from the inn.
Free, 1 hour

10:30AM

Visit the Seashore Trolley Museum

Take a trip to the Seashore Trolley Museum for a unique glimpse into the history of transportation along the coast.
A short 10-minute drive from the park.
USD12, 1.5 hours

12:00PM

Lunch at The Clam Shack

Savor delicious fried clams and lobster rolls at this renowned roadside seafood shack.
Just a 5-minute drive from the museum.
USD20, 1 hour

1:30PM

Explore Dock Square

Wander through Dock Square, lined with charming shops, art galleries, and local boutiques.
Easy walking distance from The Clam Shack.
Free, 1.5 hours

3:00PM

Go to Goose Rocks Beach

Relax on the tranquil sands of Goose Rocks Beach, perfect for lounging or taking a leisurely swim.
About a 10-minute drive from Dock Square.
Free, 2 hours

5:30PM

Dinner at Earth

Enjoy farm-to-table dining featuring seasonal ingredients and a cozy atmosphere at this Kennebunkport gem.
Returning to town center will take you about 15 minutes.
USD35, 1.5 hours

8:00PM

Drive Back to Portland

End your day with a pleasant drive back to Portland after experiencing the charm of Kennebunkport.
About a 30-minute drive back to Portland.
Free, 30 minutes
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Day 4: Adventures in Camden

Camden, Maine

8:00AM

Breakfast at Camden Diner

Enjoy a classic diner experience with hearty breakfast options at the beloved Camden Diner.
Drive approximately 1 hour from Portland to Camden.
USD15, 1 hour

9:30AM

Explore Camden Hills State Park

Hit the scenic trails at Camden Hills State Park with views that stretch over Penobscot Bay from the summit of Mount Battie.
Follow signs to the park entrance, about a 15-minute drive.
USD6, 3 hours

12:30PM

Lunch at The Waterfront Restaurant

Enjoy fresh seafood and stunning waterfront views at The Waterfront Restaurant in Camden.
A short drive from Camden Hills State Park.
USD30, 1.5 hours

2:00PM

Visit the Camden Public Library

Marvel at the architecture of the Camden Public Library and discover its enchanting gardens and reading nooks.
Approx 5-minute drive from the restaurant.
Free, 1 hour

3:00PM

Relax at Camden Harbor Park

Enjoy leisure time at Camden Harbor Park for a picturesque view of the harbor and local boats.
Right next to the library.
Free, 1 hour

4:30PM

Visit the Maine Lighthouse Museum

Learn about the history and evolution of Maine's lighthouses at this informative museum.
A 5-minute drive from the Harbor Park.
USD10, 1.5 hours

6:00PM

Dinner at the Natalie's Restaurant

Finish your day with a delightful dinner featuring New England cuisine at Natalie's, known for its warm ambiance.
Close to the Lighthouse Museum, about a 5-minute walk.
USD50, 2 hours

8:30PM

Drive Back to Portland

Conclude your Camden adventure with a scenic drive back to Portland.
Retrace your route for approximately 1 hour.
Free, 1 hour
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Day 5: Final Day in Portland

Portland, Maine

8:00AM

Breakfast at Bunker Brewing Co.

Enjoy a relaxed breakfast with local brewed coffee and light bites at this laid-back brewery setting.
Head back downtown for about a 10-minute drive.
USD15, 1 hour

9:30AM

Visit the Allagash Brewing Company

Take a guided tour of the famous Allagash Brewing Company to learn about crafting delicious Belgian-style beer.
Just a 10-minute drive from the restaurant.
USD0, 1.5 hours

11:00AM

Explore the Portland Farmers' Market

Wander through the vibrant Portland Farmers' Market to browse local produce, crafts, and bites from local vendors.
This is located a short drive from the brewery.
Free, 2 hours

1:00PM

Lunch at Salvage BBQ

Enjoy mouthwatering barbecue and craft drinks in a casual atmosphere, perfect for food lovers.
Around a 5-minute drive from the market.
USD20, 1.5 hours

3:00PM

Take a Ferry to Peaks Island

Experience a scenic ferry ride to Peaks Island, where you can explore the island’s beautiful landscapes and beaches.
The ferry terminal is near Old Port; allow 10 minutes to reach there.
USD20, 2 hours including ferry ride

5:00PM

Explore Peaks Island

Spend your afternoon wandering through Peaks Island, featuring charming streets and seaside views.
Walk around the island after disembarking the ferry.
Free, 2 hours

7:00PM

Dinner at DiMillo's on the Water

Conclude your Portland adventure with dinner at this restaurant shaped like a ship, boasting stunning views of the waterfront.
Ferry back to Portland, the restaurant is nearby in Waterfront Area.
USD40, 2 hours
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