Exploring Portland, Maine in 4 Days

Day 1: Historic Old Port

Portland, Maine

8:00AM

Breakfast at Standard Baking Co.

Start your day with freshly baked pastries and artisanal bread at this local favorite bakery.
Walk from your accommodation in the Old Port area.
$10, 1 hour

10:00AM

Explore Old Port District

Wander through cobblestone streets lined with boutiques, galleries, and restaurants in this historic waterfront district.
Short walk from Standard Baking Co.
Free, 2 hours

12:00PM

Lunch at Eventide Oyster Co.

Indulge in a variety of fresh oysters and seafood dishes at this renowned oyster bar.
Walk to Eventide Oyster Co.
$30, 1.5 hours

2:00PM

Eastern Promenade

Enjoy a leisurely stroll along the waterfront trail at Eastern Promenade Park with panoramic views of Casco Bay.
Drive or take a short taxi ride from Old Port District.
Free, 2 hours

4:00PM

Shopping at Portland Flea-for-All

Browse unique vintage finds and local crafts at this eclectic indoor market.
Short drive or taxi ride from Eastern Promenade.
$20, 1.5 hours

6:00PM

Dinner at Fore Street

Savor farm-to-table cuisine in a rustic-chic setting at this popular restaurant known for its wood-fired dishes.
Walk or short drive from Portland Flea-for-All.
$50, 2 hours
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Day 2: Scenic Cape Elizabeth

Portland, Maine

8:00AM

Breakfast at Scratch Baking Co.

Start your day with delicious pastries and coffee at this cozy bakery in South Portland.
Drive or short taxi ride from your accommodation.
$15, 1 hour

10:00AM

Portland Head Light

Visit Maine's oldest lighthouse for breathtaking views of the Atlantic Ocean and rocky coastline.
Drive or take a scenic bike ride along the coast to Cape Elizabeth.
$5, 2 hours

12:00PM

Lunch at The Lobster Shack

Enjoy fresh seafood with a view at this iconic lobster shack overlooking the ocean.
Short drive or bike ride from Portland Head Light.
$25, 1.5 hours

2:00PM

Explore Two Lights State Park

Take a leisurely walk along the cliffs and enjoy panoramic views of the Atlantic Ocean at this picturesque state park.
Short drive from The Lobster Shack.
$10, 2 hours

4:00PM

Cape Elizabeth Beaches

Relax on the sandy shores of Crescent Beach or Higgins Beach, popular spots for swimming and sunbathing.
Short drive from Two Lights State Park.
Free, 2 hours

6:00PM

Dinner at The Well at Jordan's Farm

Enjoy a farm-to-table dining experience with seasonal dishes made from locally sourced ingredients.
Drive back to Portland for dinner.
$40, 2 hours
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Day 3: Arts & Culture

Portland, Maine

9:00AM

Breakfast at Tandem Coffee + Bakery

Start your day with artisanal coffee and delicious pastries at this hip coffee shop in the East Bayside neighborhood.
Drive or short taxi ride from your accommodation.
$10, 1 hour

10:00AM

Portland Museum of Art

Explore a diverse collection of artwork, including pieces by Winslow Homer and Andrew Wyeth, at this prominent art museum.
Short drive or walk from Tandem Coffee + Bakery.
$15, 2 hours

12:00PM

Lunch at Duckfat

Indulge in creative sandwiches and Belgian-style fries cooked in duck fat at this popular eatery in the Arts District.
Short walk from Portland Museum of Art.
$20, 1.5 hours

2:00PM

Explore the Arts District

Stroll through galleries, studios, and boutiques showcasing local art and craftsmanship in this vibrant neighborhood.
Walk around the Arts District.
Free, 2 hours

4:00PM

Visit Wadsworth-Longfellow House

Tour the childhood home of poet Henry Wadsworth Longfellow, a National Historic Landmark filled with period furnishings and artifacts.
Short walk from the Arts District.
$12, 1.5 hours

6:00PM

Dinner at Central Provisions

Experience shared plates of innovative New American cuisine in a cozy, brick-walled space with an open kitchen.
Walk or short drive from Wadsworth-Longfellow House.
$45, 2 hours
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Day 4: Island Exploration

Portland, Maine

9:00AM

Breakfast at Marcy's Diner

Enjoy a hearty breakfast at this iconic diner known for its delicious pancakes and friendly atmosphere.
Drive or take a short ferry ride to Peaks Island.
$15, 1 hour

10:30AM

Peaks Island

Explore the charming island on foot or rent a bike to visit attractions like Battery Steele and the Fifth Maine Museum.
Take a ferry from Portland to Peaks Island.
$10 (round trip ferry fare), 3 hours

1:30PM

Lunch at The Cockeyed Gull

Savor seafood dishes and pub fare with a waterfront view at this casual island restaurant.
Walk from your exploration on Peaks Island.
$20, 1.5 hours

3:00PM

Relax on the Beach

Spend some time relaxing on the sandy beach or swimming in the refreshing waters of Peaks Island.
Short walk from The Cockeyed Gull.
Free, 1.5 hours

5:00PM

Ferry Back to Portland

Catch the ferry back to Portland and enjoy the scenic views of Casco Bay during the return trip.
Take the ferry back to Portland.
$10, 1 hour

6:30PM

Dinner at Scales

End your trip with a seafood feast at this upscale waterfront restaurant offering fresh catches and harbor views.
Short walk from the ferry terminal.
$60, 2 hours
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