5-Day Relaxation & Foodie Itinerary in Portland, Maine

Day 1: Explore Portland

Portland, Maine

8:00 AM

Breakfast at Becky's Diner

Start your day with a hearty breakfast at this local favorite known for its classic diner fare, including blueberry pancakes.
Short walk or drive from downtown hotels.
USD15, 1 hour

9:30 AM

Visit the Portland Head Light

Explore the iconic Portland Head Light lighthouse, where you can enjoy stunning coastal views and take photos.
Drive to Cape Elizabeth, approximately 15 minutes away.
Free, 1.5 hours

11:30 AM

Fresh Seafood Lunch at Eventide Oyster Co.

Indulge in a delicious seafood lunch, featuring their famous brown butter lobster roll and local oysters.
Return to Portland central, about 15 minutes drive.
USD30, 1.5 hours

1:00 PM

Explore the Old Port District

Stroll through the charming cobblestone streets and boutique shops filled with unique local art and handmade crafts.
Walk around the Old Port from the restaurant.
Free, 2 hours

3:00 PM

Relax at Eastern Promenade

Unwind at this beautiful park with sweeping views of Casco Bay, perfect for leisurely walks or napping on the grass.
Short drive or a nice walk from Old Port.
Free, 2 hours

5:00 PM

Dinner at Fore Street

Savor a farm-to-table dining experience with locally sourced ingredients, including wood-fired dishes inspired by New England cuisine.
Return to Fore Street, approximately 5 minutes drive.
USD50, 2 hours
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Day 2: Cultural Insights

Portland, Maine

8:00 AM

Breakfast at Tandem Coffee Roasters

Enjoy expertly brewed coffee and freshly baked pastries in a cozy, inviting atmosphere.
Located in the East End, about 10 minutes from hotel.
USD15, 1 hour

9:30 AM

Portland Museum of Art

Immerse yourself in Maine's artistic heritage and contemporary works in this beautifully curated museum.
Drive to the museum, approximately 5 minutes.
USD12, 2 hours

12:00 PM

Lunch at Duckfat

Treat yourself to duck fat fries and panini sandwiches in an eatery known for its unique flair and flavor.
Just a short drive from the museum, around 5 minutes.
USD25, 1.5 hours

1:30 PM

Wander the Portland Waterfront

Stroll along the picturesque waterfront, catching views of the marina and nearby islands.
Within walking distance from Duckfat.
Free, 2 hours

4:00 PM

Visit the Victoria Mansion

Explore this stunning 19th-century mansion known for its exquisite architecture and elegant furnishings.
Drive over within 10 minutes.
USD15, 1.5 hours

6:00 PM

Dinner at Nine Strawberrries

End your day with a farm-based meal paired with wine, featuring chef-driven dishes that highlight local flavors.
A 5-minute drive from the mansion.
USD45, 1.5 hours
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Day 3: Coastal Escapes

Cape Elizabeth, Maine

8:00 AM

Breakfast at The Good Table

Start your day with a delicious breakfast rooted in freshness at this local eatery known for its creative menu.
Drive to Cape Elizabeth, about 20 minutes.
USD20, 1 hour

9:30 AM

Explore Fort Williams Park

Visit the iconic lighthouse and stroll through the park, enjoying the beautiful ocean views and historical remains.
Located within the park, just a few minutes away.
Free, 2 hours

12:00 PM

Lunch at The Lobster Shack at Two Lights

Dig into a classic New England lobster roll while gazing at the stunning ocean scenery.
Short drive from Fort Williams Park, around 5 minutes.
USD30, 1.5 hours

1:30 PM

Explore Two Lights State Park

Spend the afternoon hiking or relaxing at this serene park that offers a perfect blend of natural beauty and coastal views.
Only a few minutes drive from The Lobster Shack.
USD5, 2 hours

4:00 PM

Relax at Crescent Beach State Park

Unwind on the soft sands of this beautiful beach, perfect for sunbathing or wandering along the coast.
Short drive from Two Lights State Park, about 10 minutes.
USD6, 2 hours

6:00 PM

Dinner at DiMillo's on the Water

Dine aboard a floating restaurant with fresh seafood offerings and stunning harbor views to finish off the day.
Head back into Portland, approximately 20 minutes drive.
USD50, 1.5 hours
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Day 4: Charming Towns

Freeport, Maine

8:00 AM

Breakfast at Wild Oats Bakery & Café

Enjoy fresh, homemade pastries and organic coffee at this local bakery known for its cozy ambiance.
Drive to Freeport, approximately 30 minutes.
USD15, 1 hour

9:30 AM

Shop at L.L. Bean Flagship Store

Visit the famed L.L. Bean store, where you can find an array of outdoor gear and apparel in a picturesque setting.
Located right in Freeport, easy to walk to.
Free, 1.5 hours

11:00 AM

Explore the Freeport Historical Society

Learn about Freeport's rich history and local cultures through engaging exhibits and events.
Walk to the location, just a few minutes away.
USD5, 1.5 hours

12:30 PM

Seafood Lunch at Harraseeket Lunch and Lobster Company

Delight in fresh, local seafood served casually, with scenic views of the harbor.
Just a short drive down the road, around 5-10 minutes.
USD30, 1.5 hours

2:00 PM

Visit Wolfe's Neck Woods State Park

Explore the scenic trails that meander through woods and along the coastline, perfect for nature lovers.
Drive to the park, approximately 15 minutes.
USD5, 2 hours

5:00 PM

Dinner at Azure Cafe

Savor a delightful dinner, featuring a menu of Maine-inspired dishes made from local ingredients.
Head back to Freeport, about 15 minutes drive.
USD40, 1.5 hours
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Day 5: Final Farewell

Portland, Maine

8:30 AM

Breakfast at The Brunch Box

Fuel your morning with unique breakfast sandwiches and fresh coffee at this quirky cafe.
Drive back to Portland, about 20 minutes.
USD15, 1 hour

10:00 AM

Visit the Maine Narrow Gauge Railroad Museum

Discover the fascinating history of railroads in Maine with engaging exhibits and a scenic train ride along the waterfront.
Short drive from breakfast, around 10 minutes.
USD10, 2 hours

12:30 PM

Lunch at the Chebeague Island Inn

Enjoy picturesque views while relishing a meal made from locally sourced ingredients in a charming coastal setting.
Drive or take a ferry to the inn, about 30 minutes.
USD40, 1.5 hours

2:00 PM

Relax at Spa at the Press Hotel

Treat yourself to a luxurious spa experience at this acclaimed hotel to end your trip feeling rejuvenated.
Return to Portland, 15 minutes drive.
USD100, 2 hours

4:30 PM

Farewell Stroll on the Promenade

Take a leisurely stroll along the Eastern Promenade to soak in the views and reflect on your journey.
A short drive over or 5-10 minute walk.
Free, 1.5 hours

6:00 PM

Dinner at Street & Co.

Finish off your foodie adventure with a Mediterranean-inspired seafood feast in an elegant setting.
Drive or walk from the promenade, about 10 minutes.
USD60, 2 hours
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