How to Spend a Few Days in Portland Maine: A Comprehensive Guide

Portland, Maine, is a charming coastal city known for its historic waterfront, vibrant arts scene, and exceptional food culture. Whether you’re a history buff, a foodie, or someone who simply loves stunning ocean views, this city has something for you. If you’re wondering how to spend a few days in Portland, Maine, this guide will help you craft the perfect itinerary filled with must-see attractions, delicious eats, and unforgettable experiences.

Day 1: Exploring the Historic Old Port and Waterfront

Morning: Arriving and Settling In

Start your adventure by checking into a cosy boutique hotel or a charming bed-and-breakfast. The Press Hotel, The Francis, and Blind Tiger are excellent options for a stylish and comfortable stay. Once you’re settled, head straight to the Old Port district.

Late Morning: Strolling Through the Old Port

The Old Port is one of the most iconic areas of Portland, featuring cobblestone streets, historic brick buildings, and a lively waterfront. Here’s what you shouldn’t miss:

• Local Shops & Boutiques – Browse unique shops selling Maine-made goods, jewellery, and souvenirs.
• Art Galleries – Stop by local galleries to admire works from talented Maine artists.
• Waterfront Walk – Enjoy picturesque harbour views along Commercial Street.

Lunch: Savoring Fresh Maine Seafood

A trip to Portland wouldn’t be complete without indulging in fresh seafood. Stop by Eventide Oyster Co. or J’s Oyster for a classic lobster roll or a hearty bowl of clam chowder.

Afternoon: Portland Museum of Art

After lunch, explore the Portland Museum of Art, home to works by Winslow Homer, Claude Monet, and many more. The museum’s blend of historic and contemporary art makes it a must-visit for culture enthusiasts.

Evening: Dinner and Nightlife in the Arts District

Wrap up your first day with dinner in the Arts District, known for its trendy restaurants and live entertainment. Some top dining spots include Central Provisions (small plates with a creative twist) and Fore Street (seasonal farm-to-table cuisine). If you’re up for a night out, check out a show at Portland Stage or State Theatre for live music.

Day 2: Nature, Lighthouses, and Coastal Adventures

Morning: Portland Head Light & Fort Williams Park

Begin your second day with a visit to Portland Head Light, Maine’s most famous lighthouse. Located in Fort Williams Park, this historic landmark offers:

• Breathtaking ocean views
• Scenic walking trails
• A small museum inside the lighthouse keeper’s quarters

Late Morning: Exploring Casco Bay by Boat

After soaking in the views at Portland Head Light, head back to the waterfront for a Casco Bay boat tour. You can choose from:

• Island ferries – Take a trip to Peaks Island for a laid-back island vibe.
• Wildlife cruises – Spot seals, seabirds, and maybe even a whale!
• Sunset sailing tours – Perfect for a romantic end to the day.

Lunch: Picnic on the Islands

If you choose to visit Peaks Island, grab some picnic essentials from Standard Baking Co. or Portland Farmers’ Market and enjoy lunch by the water.

Afternoon: Maine Maritime Museum

To learn more about Maine’s rich maritime history, visit the Maine Maritime Museum in nearby Bath. Explore shipbuilding artefacts, historic boats, and hands-on exhibits that dive into Maine’s seafaring past.

Evening: Sunset at Eastern Promenade

End your day at the Eastern Promenade, a scenic waterfront park with breathtaking sunset views over Casco Bay. Bring a blanket, relax on the grass, and soak in the beauty of Portland’s coastline.

Day 3: Food, Culture, and Shopping

Morning: Portland Farmers’ Market

Start your final day with a trip to the Portland Farmers’ Market, where you’ll find fresh produce, homemade baked goods, artisan cheeses, and handcrafted souvenirs. It’s a great way to experience the local food scene while supporting small businesses.

Late Morning: Culinary Walking Tour

Portland is a foodie’s paradise, so why not take a culinary walking tour? These guided experiences allow you to taste a variety of Portland’s specialities, including:

• Fresh seafood
• Locally roasted coffee
• Artisanal chocolates and cheeses
• Craft beers from Portland’s famous breweries

Lunch: Portland’s Famous Food Trucks

For a casual yet delicious lunch, check out Portland’s food truck scene. Popular spots include Bite Into Maine for gourmet lobster rolls and Mami for creative Japanese street food.

Afternoon: Victoria Mansion & Shopping

In the afternoon, take a tour of Victoria Mansion, an impeccably preserved 19th-century home known for its lavish interiors and Italianate architecture. Afterwards, enjoy some last-minute shopping at:

• The Merchant Co. – Handmade gifts and home decor.
• Longfellow Books – A cozy local bookstore.
• Fishermen’s Net – The perfect place to grab fresh seafood to take home.

Evening: Final Dinner & Brewery Visit

For your last night in Portland, treat yourself to a memorable dinner at Scales or The Honey Paw, both known for their creative takes on seafood. If you’re a craft beer lover, finish the night with a visit to one of Portland’s famous breweries like Allagash Brewing Company or Bissell Brothers.

Bonus Tips for Your Trip

• Best Time to Visit: Summer (June–August) is the peak tourist season, but fall (September–October) offers beautiful foliage and fewer crowds.
• Getting Around: Downtown Portland is very walkable, but renting a bike or using Uber/Lyft can be helpful for visiting lighthouses and nearby attractions.
• Packing Essentials: Bring comfortable walking shoes, a light jacket (even in summer), and a camera to capture Portland’s scenic beauty.

Portland, Maine, is the perfect destination for a short getaway, offering a mix of history, nature, and culinary delights. Whether you’re exploring the Old Port, savouring fresh lobster, or enjoying a peaceful sunset by the ocean, every moment in this charming coastal city is worth experiencing. Now that you know how to spend a few days in Portland, Maine, start planning your trip and get ready to fall in love with this beautiful New England gem.