Top Portland Art & Culture - page 2

This isn’t just another sightseeing trip—it’s a curated journey through Maine’s most iconic landmarks and hidden gems, woven together into one unforgettable day. From the elegance of Portland Head Light, the nation’s most photographed lighthouse, to the playful charm of Eartha, the world’s largest rotating globe, every stop reveals a different facet of Maine’s character. Guests walk a historic suspension bridge built by the engineers of the Brooklyn Bridge, explore the state’s proud maritime heritage in Bath, and visit the legendary L.L. Bean flagship store in Freeport. What sets this tour apart is the balance of scenery, history, and culture: stunning coastal views, hands-on heritage at museums and memorials, and Maine icons you won’t find grouped together anywhere else. And because it’s a shorter itinerary, it’s the perfect choice for cruise ship passengers or travelers with limited time who still want a rich, memorable Maine experience.

On this walking tour, we’ll explore the city’s significant role in the Underground Railroad and the individuals who helped shape its fight for freedom. The tour is self guided on our walking tour app. It's hands free, plays as you walk and you can go at your own pace, anytime, it never expires. You’ll walk through historic streets where ordinary citizens took extraordinary risks to assist those escaping slavery. We’ll visit former homes, churches, and workplaces that served as safe havens and meeting places for abolitionists, reformers, and community leaders. Each stop demonstrates how Portland’s waterfront and neighborhoods became centers of courage, compassion, and quiet resistance. Let’s start our journey at the Mariner’s Church Banquet Center, a landmark that saw both Portland’s growth and its dedication to justice.

See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship’s wheel.

Our White Mountains Day Tour offers more than just scenic views—it’s a thoughtfully curated journey through New Hampshire’s most charming towns, historic covered bridges, and hidden natural wonders. Unlike larger, rushed tours, we keep our groups small for a more personal experience, allowing time to explore, photograph, and connect with each stop. From the iconic Kancamagus Highway to the massive Madison Boulder, every stop has a story—and our guides bring it to life. Guests also have the option to add a ride on the historic Mount Washington Cog Railway for an unforgettable summit experience.

Few things are more beautiful than a majestic sunset. However to see it from the waters of Portland's magnificent Casco Bay is a truly remarkable experience. Whether a first-time kayaker or experienced hand, this 2-hour tour offers phenomenal vistas of Portland harbor and cityscsape. Your only neighbors are your guide, your small group and the wildlife as you leisurely paddle back to shore.

Explore the beauty and history of Portland with this combo of a walking and driving tour. Dig deep into the city’s history as you stroll down cobblestone streets and admire old brick architecture by the waterfront. Visit bustling neighborhoods like Old Port and the Art District, stop at shops and restaurants whenever you please, and breathe in the coastal air. Then take a drive out to the east and west promenades, before swinging down to the famous Portland Head Light lighthouse. It’s the most comprehensive way to experience this unique, quirky city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

As we cruise the waters around Portland Harbor we will make stops at Portland Breakwater Light, Spring Point Light and Ram Island Ledge Light before stopping at Maine’s oldest and most iconic lighthouse, Portland Headlight. This historic beacon, with its striking architecture and stark coastal backdrop, is a sight to behold from the perspective of the Atlantic Ocean as seafarers have done for more than 200 years. After photos and information about this iconic lighthouse, we continue the ride along the rocky shores of Cape Elizabeth to Two Lights State Park, whose twin lighthouses perch atop dramatic cliffs. Our best chance for wildlife comes during the next leg of the ride as we cruise open waters to Halfway Rock Lighthouse, a true maritime relic. Standing proudly on a remote ledge in the open ocean, it has guided mariners through thick fog and turbulent waters for over a century. Seals are often found hanging on the rocks and feeding in the nutrient-rich waters.

Unlike large group bus tours, this experience is designed to be personal, flexible, and immersive. You’ll walk the streets of Salem with a knowledgeable guide who doesn’t just point out landmarks but brings their stories vividly to life—from the haunting legacy of the Witch Trials to the maritime wealth that built the city, and the literary genius of Nathaniel Hawthorne. What makes this tour unique is the balance of history and atmosphere: you’ll explore centuries-old cemeteries and mansions, admire harbor views and gardens, and even encounter touches of pop culture like the Bewitched statue. With small groups and a customizable pace, you’ll have the freedom to linger where your interests lie most—whether it’s taking photos, diving deeper into Salem’s legends, or enjoying a quiet moment in a hidden garden. This isn’t just sightseeing—it’s a chance to experience Salem’s past and present through stories, scenery, and atmosphere in a way that big tours can’t match.

Experience the beauty of Maine’s central coast on a fully private, all-day tour designed just for you. Unlike crowded bus tours, our small-group experience offers personalized attention, comfort, and flexibility. Travel in style through autumn-kissed landscapes as your local guide leads you to handpicked highlights—like the iconic Portland Head Light, the charming harbor town of Boothbay, and the historic Fort Edgecomb. Walk the gently swaying Androscoggin Swinging Bridge, shop at the legendary L.L.Bean Flagship Store, and take in riverside views in Bath, “The City of Ships.” This is coastal Maine at its finest—tailored, immersive, and unforgettable.

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses, historic forts, and natural features. A round of drinks is included to toast the sunset with, but more beverages are available to purchase onboard.

Explore the Portland Peninsula by bike with this small-group guided tour. Start at the Eastern Promenade, making your way along the waterfront bike path until you reach the Back Cove Trail. Your guide takes you to the Old Port to see some of the City of Portland's prettiest old brick buildings, and you learn the significance of local food, history, and culture of this area.

The most immersive way to see Historic Portland is on foot. Our 1 hour 15 minute walking tour takes you down the cobblestone pathways of our historic city in search of spirits that linger from times long past. Our knowledgeable guides will enchant you with tales of Portland’s most renown ghosts as well as the area's vast and rich history. You’ll hear fascinating and spooky tales from the first European settlement in 1632 right up to the present day. Discover the many times Portland has fallen and risen anew, and hear about the restless spirits who remain, unable or unwilling to move on. Follow our guides as they lead you by lantern-light sharing the ghost stories, legends, and folklore of this beautiful city.

See some of Maine's most picturesque scenery with this private full-day tour from Portland. Your driver will pick you up at your hotel or vacation rental and take you out for a day of exploration, stopping by coastal towns, iconic lighthouses, viewpoints, and other areas of interest along the way.

Maine’s lighthouses are beautiful, but they’re even more gorgeous from the water. You’ll get those epic views and more on this scenic, intimate cruise, traveling from Portland’s Old Port to the harbor’s best sights. You’ll witness the old-school lighthouses, the islands of Casco Bay, a Civil War–era fort, and so much more. With a drink in hand, it’s a great way to start—or end—your time in Portland.

Join us for an exciting Private Coastal Tour from Portland to Camden, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is **Camden Hills State Park**, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mount Battie. We'll finish with a brief stop at the Maine State Capitol, designed by the same architect as the U.S. Capitol, offering a fascinating glimpse of Maine’s history. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!

Discover the lighthouses and coastal landmarks of Portland on a small-group biking tour. Hop on a provided bicycle and follow your guide to the Bug Light, Spring Point Ledge, and Portland Head lighthouses. Along the way, learn about their storied histories. Other highlights include the Liberty Ship Memorial, Cape Elizabeth, and Willard Beach. Set at a leisurely pace, the adventure also includes a complimentary lobster roll lunch at an award-winning food truck.

It is the only regularly operating pedicab in Portland. Portland Pedicab creates the feeling of joy for all by allowing passengers to spend the time viewing Portlands scenery while heading to their destination. This is a great mode of transportation for those that like to be outside! Music which is provided, is always an option while enjoying the views of Portland.

Experience the beauty and history of Ipswich and Cape Ann on this private tour. Wander Castle Hill’s grand estate, explore Ipswich’s heritage, and enjoy Gloucester’s seaside character. When available, Hammond Castle offers an unforgettable glimpse into medieval architecture on the New England coast. End your journey at Russell Orchards for fresh, local charm

Maine is known for its seafood, and with this tour, you'll get to learn all about the industry, with the chance to sample some local delicacies along the way. You'll take a walk along the waterfront where lobster boats dock to unload their catches before heading out to a lunch of lobster rolls served with clam or seafood chowder and craft beer or soda pop.

All of our tours are done in a comfortable vehicle with a local driver guide and can be done at your pace. Tours can always be customized to your interests. This particular tour will show you all the main sites of Portland proper and then all of the South Portland lighthouses, including admission to the Portland Headlight at Fort Williams Park. After Portland, you will head on down the highway to Kennebunkport to visit this popular coastal village that former President George W. Bush and family called their summer home. We have a standard routing but being a private tour, we can tailor your experience to you interests.

Join us for an exciting **Private Coastal Tour from Portland to Camden**, exploring the beauty and history of Maine’s coastline! Start with Bath, home to the towering USS Wyoming sculpture and rich shipbuilding heritage. In Wiscasset, stroll through “The Most Beautiful Village in Maine” and visit the world-famous Red’s Eats lobster stand. In Rockland, enjoy a walk to the lighthouse and explore its maritime charm. In Camden, wander the charming streets, enjoy lunch, and see a unique waterfall flowing through town. The highlight of the tour is **Camden Hills State Park**, where you’ll take in the most breathtaking views of Midcoast Maine from the summit of Mount Battie. We'll finish with a brief stop at the Maine State Capitol, designed by the same architect as the U.S. Capitol, offering a fascinating glimpse of Maine’s history. This fun and adventurous tour is perfect for exploring Maine’s hidden gems. Book now to experience the best of the coast!

Experience the breathtaking beauty of New England’s White Mountains on this private guided tour from Portland, Maine. This full-day adventure combines spectacular mountain scenery, historic rail travel, charming villages, and iconic landmarks that showcase New Hampshire’s famous mountain region. The highlight of the tour is the Mount Washington Cog Railway, where guests board the historic train and travel to the summit of Mount Washington, the highest peak in the northeastern United States. At the summit, guests can enjoy panoramic views, explore the observation area, and visit the small museum. The tour also includes scenic drives along portions of the famous Kancamagus Highway, widely considered one of the most beautiful mountain drives in the country. Along the way we visit picturesque villages such as Jackson and North Conway, see the historic Mount Washington Hotel, and stop at scenic overlooks and waterfalls that make the White Mountains unforgettable.

Experience the beauty of coastal Maine on this private guided tour featuring iconic landmarks, scenic harbors, and charming coastal villages. Your journey begins at Portland Head Light, one of the most photographed lighthouses in the United States, where dramatic rocky cliffs and sweeping Atlantic views create unforgettable photo opportunities. From there, travel along Maine’s scenic coastline to the picturesque harbor village of Boothbay Harbor. Walk across the historic Footbridge, built in 1901, and enjoy views of working lobster boats, quiet marinas, and classic New England waterfront scenery. Guests also have the option to enjoy lunch along the harbor at a unique restaurant built from a historic tugboat. With a knowledgeable local guide sharing stories and insights throughout the journey, this private coastal Maine tour offers the perfect blend of history, scenery, and authentic coastal charm.

Go beyond the sights of Portland, Maine and take a day trip to Salem, Massachusetts. The town of Salem is known for its famous witch trials that took place in 1692. Learn about the history of Salem on a guided tour through the town and see several landmarks including the Salem Witch Museum, the memorial, and Phillips House. On your way to Salem, stop in Kennebunkport to explore the historic village.