Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

3-Day Relaxation, Nature, and Foodie Train Trip in Maine

Viewed by 103 travelers

Day 1: Arrival and Exploration

Portland, Maine on May 8, 2025

9:00AM

Arrival at Portland

Arrive in Portland via Amtrak Downeaster and prepare for a relaxing exploration of the city.
Take a taxi or ride share to your hotel.
USD0, 1 hour

10:30AM

Breakfast at The Green Elephant

Enjoy a delicious brunch at The Green Elephant, where you can find fantastic vegetarian plate options amidst Maine's freshest ingredients.
Walking distance from your hotel, located in the Old Port district.
USD25, 1 hour

12:00PM

Visit Portland Head Light

Wander over to the iconic Portland Head Light in Fort Williams Park for stunning coastal views and a peaceful environment.
Drive or arrange a local ride to Fort Williams Park.
USD0, 2 hours

2:00PM

Lunch at Eventide Oyster Co.

Savor Maine Lobster rolls at Eventide Oyster Co., a well-known spot for shellfish lovers.
Head back to downtown Portland.
USD30, 1 hour

3:30PM

Explore the Old Port District

Stroll through the cobbled streets of the Old Port district, full of boutique shops and local art galleries.
Walking distance in the Old Port area.
USD0, 2 hours

6:00PM

Dinner at DiMillo's On the Water

Enjoy fresh seafood and stunning waterfront views at DiMillo's, ending your day with a delightful lobster mac and cheese.
Walk from the Old Port area.
USD50, 2 hours
Find Hotels in Portland

Day 2: Nature and Shopping Fun

Freeport, Maine on May 9, 2025

8:00AM

Breakfast at your hotel

Start your day leisurely with breakfast in your hotel, fueling up for a day of exploration.
Enjoy more dining options near your hotel.
USD15, 1 hour

9:30AM

Travel to Freeport

Head to Freeport for a day of shopping and scenery in this charming town.
Drive or take a local bus to Freeport (approximately 30 minutes).
USD10, 1 hour

10:30AM

Explore L.L.Bean

Visit the flagship L.L.Bean store and enjoy the outdoor displays and petting corral.
Located centrally in Freeport.
USD0, 1 hour

12:00PM

Lunch at Linda Bean's Maine Lobster

Indulge in another lobster experience with a lobster roll at Linda Bean's Maine Lobster.
Walking distance from L.L.Bean.
USD25, 1 hour

1:30PM

Visit Wolfe's Neck Woods State Park

Enjoy the natural beauty through a scenic trail walk in Wolfe's Neck Woods State Park.
Short drive from Freeport town (around 10 minutes).
USD0, 2 hours

4:00PM

Return to Freeport for Shopping

Spend the afternoon shopping at local boutiques and art shops for unique finds.
Back to downtown Freeport.
USD0, 2 hours

6:30PM

Dinner at The Maine Grill

Delight in classic Maine dishes, featuring plenty of lobster options at The Maine Grill.
Located near your shopping area.
USD45, 2 hours
Find Hotels in Freeport

Day 3: Seaside Relaxation

Rockland, Maine on May 10, 2025

8:00AM

Breakfast at your hotel

Enjoy a relaxing breakfast before departing for Rockland.
Have breakfast prepared in your hotel room or at a local café.
USD15, 1 hour

9:30AM

Travel to Rockland

Head to Rockland for a beautiful seaside day filled with art and culture.
Drive or take a local bus to Rockland (approximately 30 minutes).
USD10, 1 hour

10:30AM

Visit Farnsworth Art Museum

Discover American art and Maine artists at the Farnsworth Art Museum.
Browse around the downtown Rockland area.
USD15, 1.5 hours

12:00PM

Lunch at The Pearl

Savor a fresh seafood platter featuring a lobster special at The Pearl, a local favorite.
Short walk starting from the museum.
USD40, 1 hour

1:30PM

Afternoon at Rockland Harbor

Relax and unwind with a scenic stroll along Rockland's harbor, a picturesque locale.
Take a short walk from The Pearl.
USD0, 1 hour

3:00PM

Explore the local artisan shops

Spend your final afternoon chatting with local artists and checking out unique souvenirs.
Just a couple of blocks from the harbor.
USD0, 2 hours

6:00PM

Departure Dinner at The Landings Restaurant

End your trip with a fine dining experience at The Landings, enjoying their exquisite lobster dinner before heading back.
A quick drive or walk from downtown.
USD60, 2 hours
Find Hotels in Rockland
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version

More About Maine

Trip Packing List: Maine — June 2026 (Girls' Weekend: visiting, dinner out, shopping)
Packing List
Trip Packing List: Maine & Eastern Canada — June 10th (Relaxing + Hiking)
Packing List
June Weather in Portland, ME: Early Summer on the Coast
Weather Guide
Itinerary created by AI-assisted, human-reviewed

Plan Your Maine Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go