Portland has evolved from a modest seaport into Maine's largest metropolitan area and one of the most vibrant towns on the East Coast. Over the past 400 years, urban renewal projects have revitalized the historic waterfront and downtown areas.

Trendy restaurants and galleries now sit alongside charming heritage landmarks, creating a delightful blend of old and new. Despite its cultural and culinary allure, Portland remains a bustling fishing port, offering a mix of grit and elegance.

With cobblestoned streets, a scenic coastline, and a thriving arts and food scene, Portland has a way of captivating visitors. Whether you're a New England local or a traveler, this guide provides the perfect itinerary for spending one unforgettable day in Portland, Maine.

How to Get to Portland, Maine from Boston

Drive to Portland

Lykkers, driving from Boston to Portland takes just around 2 hours. Once in Portland, a car won’t be necessary except for visiting the lighthouse, as the city is highly walkable. Parking garages and street parking are conveniently available downtown.

Take the Amtrak Downeaster Train

The Amtrak Downeaster offers daily departures from Boston’s North Station to Portland. The journey takes about 2.5 hours, with tickets costing around $35 each way. Upon arrival, downtown Portland is 2 miles away, accessible via Uber, bus, or a pleasant walk.

Take the Concord Coach Bus

The Concord Coach Bus runs from Boston’s South Station to Portland in about 2 hours, with tickets priced at $27 each way. The bus stops at the Portland Transportation Center, where Uber, bus, or walking options can bring you to the city center.

How to Spend the Perfect Day in Portland

Marvel at the Portland Head Light

Start the day at the iconic Portland Head Light in Fort Williams Park. Built in 1791, it’s Maine’s oldest lighthouse and a must-visit landmark. The park offers breathtaking views, ample parking, and picnic areas. Premium parking spaces require a fee from April 1 to November 15, but free overflow parking is available.

Lunch at Flatbread Company

For lunch, head to Flatbread Company for delicious wood-fired flatbread pizzas with waterfront views. Vegetarian and vegan-friendly options, like the Southwest flatbread, make it a favorite. Parking garages nearby allow you to explore the area on foot afterward.

Walk Along Commercial Street

After lunch, stroll down Commercial Street along Portland’s waterfront. Explore boutiques, local shops, and eateries offering renowned treats like lobster rolls or Holy Donut’s potato-based donuts.

Explore Old Port

Old Port’s cobblestone streets are perfect for wandering and discovering. Visit local boutiques like Bobbles and Lace for unique finds or shop along Exchange Street. Coffee enthusiasts can grab a pick-me-up at Bard Coffee, while art lovers can explore murals, galleries, or the Portland Museum of Art.

Enjoy a Pre-Dinner Drink

Dear Lykkers, choose your preferred spot for a pre-dinner drink.

Have Dinner at Sur Lie

End the day with a memorable dinner at Sur Lie, a tapas-style, woman-owned restaurant and James Beard semifinalist in 2023. Known for its bold flavors and creative dishes, the menu showcases locally sourced ingredients. Highlights include the chef’s board, wild arugula salad, corn fritters, smoked butternut squash, and inventive desserts like parsnip cake with carrot curry ice cream.

Portland, Maine, effortlessly combines charm, culture, and culinary excellence, making it a destination worth exploring again and again.