5-Day Nature Itinerary in Portland, Maine

Day 1: Exploring Portland

Portland, ME on October 18, 2024

8:00AM

Breakfast at The Holy Donut

Start your day with a unique treat at The Holy Donut, known for its delicious potato-based donuts that are a local favorite.
Head downtown Portland, easy walking distance from most hotels.
USD10, 1 hour

9:30AM

Visit Eastern Promenade

Stroll along the Eastern Promenade for stunning views of Casco Bay while enjoying the refreshing morning air and vibrant fall foliage.
Continue walking from The Holy Donut to the Eastern Promenade.
Free, 2 hours

12:00PM

Lunch at Eventide Oyster Co.

Savor some fresh, locally-sourced seafood at Eventide Oyster Co., known for their mouthwatering lobster rolls.
Drive or take a short taxi from Eastern Promenade to Eventide Oyster Co.
USD25, 1.5 hours

2:00PM

Visit Fort Williams Park

Explore Fort Williams Park, home to the iconic Portland Head Light, where you can take in the scenic views and photograph the historic lighthouse.
Drive 15 minutes from Eventide to Fort Williams Park.
Free, 2 hours

5:00PM

Dinner at The Lobster Shack

End your day with a casual dinner at The Lobster Shack, famous for its seafood dishes served right by the water.
Short walk from Fort Williams Park to The Lobster Shack.
USD30, 1.5 hours
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Day 2: Casco Bay Islands Adventure

Portland, ME on October 19, 2024

7:30AM

Breakfast at Scratch Baking Co.

Fuel up with freshly baked goods and coffee at Scratch Baking Co., a local bakery known for its pastries.
Drive 10 minutes to the bakery from your hotel.
USD15, 1 hour

9:00AM

Ferry to Peaks Island

Catch the ferry from Portland to Peaks Island, where you can enjoy a day of biking and exploring the scenic, coastal paths.
Walk to the ferry terminal (about 5 minutes).
USD12 round trip, 20 minutes each way

10:00AM

Bike Around Peaks Island

Rent a bike and ride around the island, soaking in views of the ocean and charming cottages.
Bike rental available near the ferry dock.
USD20, 3 hours

1:30PM

Lunch at The Island Market

Grab a casual lunch at The Island Market, offering fresh sandwiches and salads perfect for outdoor dining.
Bike to the Island Market located centrally on Peaks Island.
USD15, 1 hour

2:30PM

Explore Ocean and Cliff Paths

Continue your exploration by walking the scenic ocean and cliff paths, enjoying the beautiful coastal views.
Head out on foot from the Island Market.
Free, 2 hours

5:00PM

Return Ferry to Portland

Catch the ferry back to Portland as the sun sets, a perfect end to your day on the water.
Walk back to the ferry terminal.
Included in previous ferry cost, 20 minutes

6:00PM

Dinner at Duckfat

Indulge in delicious meals at Duckfat, famous for its fries and sandwiches, perfect for refueling after a fun day.
Drive from the ferry terminal to Duckfat, about 5 minutes.
USD30, 1.5 hours
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Day 3: Adventure in Acadia National Park

Acadia National Park, ME on October 20, 2024

6:30AM

Breakfast at Home Kitchen Cafe

Visit Home Kitchen Cafe for a wholesome breakfast featuring local ingredients to prepare you for a day in nature.
Drive from Portland to Bar Harbor, approximately 3 hours.
USD20, 1.5 hours

9:00AM

Hiking Cadillac Mountain

Begin your Acadia adventure by hiking Cadillac Mountain, which boasts stunning panoramic views of the park and coastline.
Follow signs to Cadillac Mountain, the most popular trailhead.
Free, 2.5 hours

12:00PM

Lunch at Jordan Pond House

Enjoy lunch overlooking Jordan Pond, famous for its popovers and view of the Bubbles.
Drive to Jordan Pond House, about 30 minutes from Cadillac Mountain.
USD25, 1.5 hours

2:00PM

Walk the Jordan Pond Loop

Stroll the picturesque Jordan Pond Loop, perfect for enjoying the fall foliage and tranquil waters.
Trailhead is located near Jordan Pond House.
Free, 2 hours

5:00PM

Dinner at The Side Street Cafe

Refuel at The Side Street Cafe, famous for their lobster rolls and friendly atmosphere.
Drive to Bar Harbor from Jordan Pond (about 30 minutes).
USD30, 1.5 hours
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Day 4: Coastal Relaxation

Cape Elizabeth, ME on October 21, 2024

8:00AM

Breakfast at the Beach Shack

Enjoy a delightful breakfast at the Beach Shack, featuring local eggs and breakfast sandwiches.
Drive back to Cape Elizabeth from Bar Harbor (approx. 3 hours).
USD15, 1 hour

9:30AM

Visit Cape Elizabeth Lighthouse

Visit the iconic Cape Elizabeth Lighthouse, perfect for picturesque photos against the rugged coastline.
Drive to the lighthouse (about 10 minutes from the Beach Shack).
Free, 1 hour

11:00AM

Explore Fort Williams Park

Wander through Fort Williams Park again, taking time to enjoy any spots you may have missed.
Short drive back to Fort Williams Park.
Free, 1.5 hours

12:30PM

Lunch at Sea Glass Restaurant

Dine at Sea Glass Restaurant with stunning ocean views and farm-to-table cuisine featuring local seafood.
Drive to Sea Glass, along Route 77, about 15 minutes.
USD35, 1.5 hours

2:00PM

Hiking at Cape Elizabeth Trails

Enjoy the afternoon hiking along the scenic trails of Cape Elizabeth, surrounded by stunning natural beauty and wildlife.
Trailheads are easily accessible by car from Sea Glass.
Free, 2 hours

5:00PM

Dinner at The Good Table

Enjoy a cozy dinner at The Good Table, serving a variety of local dishes sourced from Maine farms.
Drive to The Good Table from the trails (under 10 minutes).
USD30, 1.5 hours
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Day 5: Final Day in Portland

Portland, ME on October 22, 2024

8:00AM

Breakfast at Bayside Bowl Cafe

Relax and enjoy breakfast at Bayside Bowl Cafe, a vibrant spot known for its laid-back atmosphere and delicious dishes.
Drive back to Portland (approx. 20 minutes).
USD15, 1 hour

9:30AM

Visit Portland Museum of Art

Admire the collections at the Portland Museum of Art, which features a wide range of exhibits from classic to contemporary art.
Short drive or walk from the cafe to the museum.
USD15, 2 hours

12:00PM

Lunch at Fore Street Restaurant

Dine at Fore Street, where you'll experience modern American cuisine with an emphasis on local ingredients.
Short walk from the museum to Fore Street Restaurant.
USD40, 1.5 hours

2:00PM

Explore the Old Port District

Stroll through the scenic Old Port District, known for its brick streets and historic architecture, great for last-minute shopping and exploring.
Easy walk from Fore Street to the Old Port.
Free, 2 hours

5:00PM

Dinner at J’s Oyster

Finish your adventure with a memorable dinner at J's Oyster, where you can enjoy fresh seafood in a lively setting.
Drive to J's Oyster from Old Port (about 5 minutes).
USD30, 1.5 hours
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