Portland, Maine Exploration

Day 1: Historic Old Port

Portland, Maine

8:00AM

Breakfast at Becky's Diner

Start your day with a classic Maine breakfast at Becky's Diner, known for its delicious blueberry pancakes and seafood omelettes.
Walk or take a short ride to Becky's Diner located on Commercial Street.
$10-20, 1 hour

10:00AM

Explore Old Port District

Stroll through the cobblestone streets of Old Port, lined with boutique shops, art galleries, and seafood restaurants.
Walk around the area, check out shops like Sea Bags and Maine Craft Distilling.
Free, 3 hours

1:00PM

Lunch at Eventide Oyster Co.

Enjoy a fresh seafood lunch at Eventide Oyster Co., known for their lobster rolls and oyster selection.
Eventide Oyster Co. is a short walk from Old Port district.
$20-30, 1.5 hours

3:00PM

Visit Portland Museum of Art

Immerse yourself in art and culture at the Portland Museum of Art, showcasing contemporary and historic works.
Walk or take a short ride to the museum on Congress Street.
$10-15, 2 hours

6:00PM

Dinner at Street & Co.

Indulge in a fine dining experience at Street & Co., known for its fresh seafood dishes and rustic ambiance.
Street & Co. is located in Old Port District.
$30-50, 2 hours
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Day 2: Portland Head Light & Fort Williams Park

Portland, Maine

8:00AM

Breakfast at Standard Baking Co.

Start your day with artisanal pastries and coffee at Standard Baking Co. near the waterfront.
Walk or bike to Standard Baking Co. in the Old Port district.
$5-10, 1 hour

10:00AM

Visit Portland Head Light

Explore the iconic Portland Head Light, Maine's oldest lighthouse, and enjoy breathtaking views of the Atlantic Ocean.
Drive or take a short ride to Cape Elizabeth where the lighthouse is located.
$5-10 for parking, 2 hours

1:00PM

Picnic at Fort Williams Park

Have a picnic lunch at Fort Williams Park overlooking the ocean and explore the historic ruins and bunkers.
Walk around the park within walking distance from the lighthouse.
Free, 1.5 hours

3:00PM

Hike or Bike at Eastern Promenade Trail

Enjoy a scenic hike or bike ride along the Eastern Promenade Trail, offering stunning views of Casco Bay.
Drive or bike to the trail starting point.
Free, 2 hours

6:00PM

Dinner at The Honey Paw

Savor modern Asian-inspired dishes at The Honey Paw, a popular restaurant in the Arts District.
Head to The Honey Paw located on Middle Street.
$20-30, 2 hours
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Day 3: Arts District & Breweries

Portland, Maine

9:00AM

Breakfast at Tandem Coffee + Bakery

Start your day with a delicious breakfast and artisanal coffee at Tandem Coffee + Bakery in the Arts District.
Walk or take a short ride to Tandem Coffee + Bakery on Congress Street.
$10-15, 1 hour

10:00AM

Explore Arts District

Discover the vibrant Arts District, home to art galleries, theaters, and eclectic shops showcasing local artists.
Stroll along Congress Street and visit spaces like SPACE Gallery and Portland Stage.
Free, 2 hours

12:00PM

Lunch at Duckfat

Indulge in gourmet sandwiches and crispy fries cooked in duck fat at the renowned Duckfat restaurant.
Walk to Duckfat located on Middle Street.
$15-20, 1.5 hours

2:00PM

Brewery Tour at Allagash Brewing Company

Embark on a guided tour of Allagash Brewing Company and sample a variety of Belgian-inspired beers.
Drive or take a short ride to the brewery in Industrial Way.
$10-15, 2 hours

6:00PM

Dinner at Central Provisions

Enjoy a culinary journey through small plates at Central Provisions, a trendy spot for modern American cuisine.
Head to Central Provisions in the Arts District for a unique dining experience.
$30-40, 2 hours
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Day 4: Casco Bay Islands Adventure

Portland, Maine

8:00AM

Breakfast at The Porthole Restaurant

Start your day with a hearty breakfast at The Porthole Restaurant before heading out to the islands.
The Porthole Restaurant is located near the waterfront on Custom House Wharf.
$10-15, 1 hour

9:00AM

Ferry to Peaks Island

Take a ferry from Casco Bay Lines to Peaks Island for a day of exploration and outdoor activities.
Head to the Casco Bay Lines Terminal on Commercial Street to catch the ferry.
$7-15 for ferry ticket, 3 hours

1:00PM

Bike or Kayak Rental on Peaks Island

Rent a bike or kayak on Peaks Island and explore the scenic trails or paddle along the coast.
Rentals are available near the ferry terminal on the island.
$15-30, 2 hours

4:00PM

Relax on the Beach or Enjoy a Drink at Jones Landing

Unwind on the sandy beach or grab a refreshing drink at Jones Landing overlooking the harbor.
Walk to the beach or Jones Landing from the ferry terminal area.
Free, 1.5 hours

6:00PM

Dinner at The Cockeyed Gull

End your island adventure with a seafood dinner at The Cockeyed Gull, known for its lobster dishes and harbor views.
The Cockeyed Gull is located near the ferry terminal on Peaks Island.
$20-30, 2 hours
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