Portland, Maine, is a charming coastal city that seamlessly blends rich history, vibrant culture, and stunning natural beauty. Whether you’re a history buff, a foodie, or an outdoor enthusiast, Portland offers a plethora of unique experiences to make your visit unforgettable. Here are some top activities and tours in Portland, many of which are bookable through Viator.com.

Experience Portland’s rich maritime history from the water on a lighthouse cruise. As you navigate through Casco Bay, you’ll encounter historic forts, traditional lobster boats, and several of Portland’s iconic lighthouses, including the renowned Portland Head Light, Maine’s oldest lighthouse. This leisurely cruise offers both a dive into Portland’s past and a scenic adventure suitable for all ages.

Get acquainted with Portland’s most beloved sights aboard an open-air trolley. This narrated journey covers landmarks such as the Portland Observatory and the Wadsworth-Longfellow House. The tour culminates with a visit to the city’s most famous landmark, the Portland Head Light, offering a comprehensive overview of Portland’s rich history and architectural beauty.

Uncover the lesser-known stories of Portland’s past on a guided walking tour. This small-group experience takes you through downtown and the Old Port, highlighting hidden landmarks and sharing narratives of Wabanaki leaders and other figures often omitted from traditional history books. It’s an enlightening journey through centuries of destruction, revival, and underrepresented perspectives.

Portland is renowned as one of the country’s top brewing capitals. Join a small-group tour that whisks you to three of its highlight breweries, including local legends like Shipyard Brewing. Go behind the scenes to learn about the beer-making process and enjoy numerous tastings, making it a must-do for beer enthusiasts.

Maine is synonymous with seafood, and this tour offers an immersive experience into the local industry. Stroll along the waterfront where lobster boats dock before heading to a lunch featuring lobster rolls served with clam or seafood chowder and craft beer or soda. It’s a delectable journey for seafood aficionados.

Board the Elizabeth Grace near the Portland ferry terminal for a serene sunset cruise around Portland Harbor. As the sun sets, enjoy views of lighthouses, historic forts, and playful seals. Local craft beer is available on board, enhancing the romantic ambiance as the town lights up against the evening sky.

For a personalized experience, charter a vintage lobster boat and set sail into Casco Bay. This two-hour tour offers great views of the Maine coastline, passing by four lighthouses. Learn about local nautical history from a knowledgeable captain while enjoying the scenic beauty.

The Portland Freedom Trail is a self-guided walking tour that delves into the city’s African American history. Established in 2007, the 2-mile course passes through Portland’s oldest areas, featuring thirteen points of interest related to the Underground Railroad and significant historical figures. It’s a profound journey into Portland’s role in the fight for freedom.

At the northeastern end of Portland’s peninsula lies Munjoy Hill, a largely residential area offering panoramic views of Casco Bay and Back Cove. The Eastern Promenade, a park designed by the Olmsted Brothers, features rolling fields, public gardens, playgrounds, and a small public beach. It’s an ideal spot for walking, running, cycling, or simply soaking in the scenic vistas.

Portland hosts a variety of food and beverage festivals throughout the year, celebrating its rich culinary scene. Events like the Greek Festival in June, Harvest on the Harbor in October, and Maine Restaurant Week in March offer visitors a chance to indulge in local flavors and traditions. These festivals provide a vibrant atmosphere and a taste of Portland’s gastronomic delights.

The Old Port District is a historic area known for its cobblestone streets, 19th-century brick buildings, and vibrant waterfront. It’s a hub for boutique shopping, dining, and nightlife. Stroll through the district to experience the charm of Portland’s maritime heritage, visit local shops, and enjoy fresh seafood at one of the many restaurants.

Art enthusiasts will appreciate the Portland Museum of Art, which houses an extensive collection of American, European, and contemporary art. The museum features works by renowned artists such as Winslow Homer, whose studio is also part of the museum’s offerings. Special exhibitions and events are held throughout the year, making each visit unique.

A short ferry ride from Portland’s waterfront takes you to Peaks Island, a quaint destination perfect for a day of exploration. Rent a bike or golf cart to tour the island, visit the small shops and galleries, and relax on the beaches. The island’s laid-back atmosphere provides a peaceful retreat from the city’s bustle.

The Merrill Auditorium is a must-visit for lovers of performing arts. This historic venue in the heart of Portland hosts a variety of concerts, Broadway shows, and performances throughout the year.

Why Visit:

• • Experience the grandeur of live music, opera, or a Broadway-style production.
  • Marvel at the incredible acoustics and the historic Kotzschmar Organ, one of the few remaining municipal pipe organs in the U.S.
  • Perfect for an evening of entertainment after a day of exploring the city.

Tip:

Check the event calendar in advance, as tickets to popular shows sell out quickly.

Step back in time and explore Maine’s railway history at the Maine Narrow Gauge Railroad Museum. Perfect for families or history enthusiasts, this small museum offers a nostalgic look at a bygone era of train travel.

What to Expect:

• • Explore restored narrow-gauge train cars and exhibits showcasing the history of railways in Maine.
  • Take a short ride along Casco Bay on a historic narrow-gauge train.
  • Kids will enjoy climbing aboard the trains and learning about their role in Maine’s history.

Pro Tip:

The train ride is especially scenic during fall when the foliage creates a colorful backdrop along the tracks.

For outdoor adventurers, exploring Casco Bay by kayak or paddleboard is a must. Paddle through the calm waters while enjoying views of the coastline, lighthouses, and islands.

Why It’s Unique:

• • Rent equipment or join a guided tour to learn about the bay’s history and marine life.
  • Spot seals, seabirds, and lobstermen at work as you paddle through the bay.
  • Perfect for solo travelers, couples, or families looking for an active way to enjoy Portland’s natural beauty.

Tip:

Guided sunset paddle tours offer magical views of the city as it lights up for the evening.

The Casco Bay Islands, including Peaks Island, Great Diamond Island, and Long Island, are a quick ferry ride from Portland and offer a quiet escape from the city.

What to Do on the Islands:

• • Peaks Island: Rent a bike or golf cart to explore this laid-back island. Visit its quirky Umbrella Cover Museum or relax on the rocky beaches.
  • Great Diamond Island: Known for its upscale atmosphere, this island offers walking trails, secluded beaches, and historic remnants from its military past.
  • Long Island: Perfect for a day of sunbathing, picnicking, and exploring Maine’s unspoiled coastline.

Why It’s Worth It:

The ferry ride itself offers stunning views of Portland’s skyline, the harbor, and the surrounding islands.

No trip to Portland is complete without visiting Standard Baking Co., one of the city’s most beloved bakeries. Located on the waterfront, this bakery is a foodie’s dream, with an array of freshly baked pastries, bread, and treats.

Must-Try Items:

• • The flaky almond croissants are legendary.
  • Try the chocolate bouchons, brioche rolls, and hearty sourdough bread.
  • Pair your treat with a coffee and enjoy views of the harbor.

Pro Tip:

Arrive early in the morning to get the freshest pastries before they sell out!

Step into the opulent world of the 19th century at the Victoria Mansion. This historic home, also known as the Morse-Libby House, is one of the finest examples of Italianate architecture in the United States.

Why Visit:

• • Admire the lavish interiors, including ornate frescoes, carved woodwork, and stunning furnishings.
  • Learn about the history of Portland’s wealthy merchants and their influence on the city.
  • Seasonal decorations during the holidays make the mansion especially magical.

Perfect For:

History enthusiasts and architecture lovers looking to explore Portland’s cultural heritage.

For a once-in-a-lifetime experience, book a whale-watching tour and witness these magnificent creatures in their natural habitat.

What to Expect:

• • Cruise through the Gulf of Maine with experienced guides who help you spot humpback, minke, and fin whales.
  • Learn about marine life, local ecosystems, and conservation efforts.
  • Tours are seasonal, typically running from May to October, when whales migrate through the area.

Why It’s Unique:

Few experiences compare to the thrill of seeing whales breaching and spouting in the open ocean.

The Portland Observatory, built in 1807, is the only remaining historic maritime signal tower in the United States. Climbing this landmark offers an educational and scenic experience.

Why Visit:

• • Climb the tower for spectacular panoramic views of Portland and Casco Bay.
  • Learn about the tower’s history and its role in communicating with ships arriving in the harbor.
  • A knowledgeable guide shares stories and details about Portland’s maritime heritage.

Pro Tip:

• Visit on a clear day for the best views, especially at sunset.

Portland, Maine, is a gem of the Northeast, offering a diverse mix of activities, history, food, and outdoor adventures.

 From cruising past historic lighthouses to savoring world-class seafood and exploring charming islands, this city has something for every traveler. Whether you’re interested in cultural tours, outdoor excursions, or culinary experiences, Portland’s unique charm will leave you wanting more.

Ready to experience the magic of Portland, Maine? Plan your trip today and discover why this small city continues to capture the hearts of visitors from around the world.