5 day itinerary for Portland Maine

Itinerary

Portland, Maine, is a delightful blend of culinary delights, rich history, charming shops, and beautiful coastal views. Here’s a fun and engaging 5-day itinerary that caters to your interests in food, consignment shopping, history, and beach time. Let’s dive in!

## Day 1: Arrival and Exploring the Old Port

Morning:

• Arrive in Portland and check into your hotel or cozy Airbnb. If you’re looking for a unique stay, consider a boutique hotel in the Old Port area.
• Start your day with breakfast at The Holy Donut. Their potato donuts are a must-try!

Afternoon:

• Stroll through the Old Port district. This area is filled with cobblestone streets, historic buildings, and charming shops. Pop into some consignment stores like Rerun and Maine Vintage for unique finds.
• For lunch, grab a bite at Eventide Oyster Co.. Their lobster roll is legendary!

Evening:

• Enjoy a leisurely dinner at Fore Street, known for its farm-to-table approach and wood-fired dishes. Make sure to reserve a table in advance!
• After dinner, take a walk along the waterfront and soak in the beautiful views of the harbor.

## Day 2: History and Culture

Morning:

• Start your day with breakfast at Becky’s Diner, a local favorite for hearty meals.
• Head to the Portland Museum of Art to explore its impressive collection, including works by Maine artists.

Afternoon:

• Visit the Victoria Mansion, a stunning example of Italianate architecture and a glimpse into 19th-century life.
• For lunch, try Duckfat, famous for its Belgian fries and panini sandwiches.

Evening:

• Take a historical walking tour of the city. There are several options available, including ghost tours or tours focusing on the city’s maritime history.
• Dinner at Central Provisions, where you can enjoy small plates and a great selection of local wines and craft beers.

## Day 3: Beach Day at Cape Elizabeth

Morning:

• After breakfast at Tandem Coffee Roasters, head out to Cape Elizabeth. It’s about a 15-minute drive from Portland.
• Spend the morning at Fort Williams Park, where you can explore the historic lighthouse and enjoy the stunning coastal views.

Afternoon:

• Pack a picnic lunch or grab a sandwich from The Lobster Shack at Two Lights. Enjoy your meal with a view of the ocean!
• Spend the afternoon at Crescent Beach State Park. Relax on the sandy beach, take a swim, or stroll along the shore.

Evening:

• Head back to Portland and freshen up.
• For dinner, indulge in a seafood feast at J’s Oyster, where you can enjoy fresh oysters and other local seafood dishes.

## Day 4: More Food and Shopping

Morning:

• Breakfast at The Front Room, known for its delicious brunch options.
• Afterward, visit the Maine Historical Society to learn more about the state’s rich history.

Afternoon:

• Explore the East End and check out some more consignment shops like The Green Hand Bookshop and Maine Craft Distilling for unique local products.
• For lunch, stop by Bite into Maine for some of the best lobster rolls in town.

Evening:

• Take a sunset cruise around Casco Bay. It’s a fantastic way to see the islands and enjoy the beautiful scenery.
• Dinner at Scales, where you can enjoy fresh seafood with a view of the harbor.

## Day 5: Relax and Reflect

Morning:

• Enjoy a leisurely breakfast at Flatbread Company, where you can savor wood-fired pizzas and local ingredients.
• Spend your morning at Portland Head Light in Cape Elizabeth. It’s one of the most photographed lighthouses in the U.S. and offers beautiful walking trails.

Afternoon:

• Head back to Portland and visit the Portland Farmers’ Market (if it’s a Wednesday or Saturday) for local produce and artisanal goods.
• For lunch, try The Thirsty Pig, known for its house-made sausages and craft beer.

Evening:

• Spend your last evening at The Press Hotel for a cocktail at their rooftop bar, enjoying the city skyline.
• For your farewell dinner, treat yourself to a meal at Street & Co., where you can indulge in Mediterranean-inspired seafood dishes.

Wrap-Up

And there you have it! A delightful 5-day itinerary in Portland, Maine, filled with food, history, shopping, and beach time. Each day is designed to give you a taste of what makes this city so special. Enjoy your trip, and don’t forget to take lots of pictures! 🌊🍽️🏖️