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Visit Portland’s scenic coast, historic sites and most vibrant neighborhoods with a sightseeing and shopping tour on a classic fire engine. Get great views of picture-perfect lighthouses and architecture from high up on the engine, and listen to live narration as you tour the city. Learn about Portland’s maritime past as you explore cobblestone streets with enjoy plenty of time to browse souvenir shops and sample the area’s most distinctive foods. Finish your tour in the heart of downtown, near historic wharves, restaurants and boutiques.

Food lovers can explore Portland's historic Old Port independently, but to uncover the best places serving traditional local fare, you really need a guide to lead the way. Taste the best that Portland has to offer on this guided foodie walking tour, complete with stops at up to seven different eateries—and enough tastings to replace a meal. Along the way, your guide offers some stories about Portland's food scene, so you can get familiar with the local culinary stalwarts.

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you'll board a comfortable vessel equipped for a thrilling marine adventure. As we cruise along the rugged coastline, keep your eyes peeled for the majestic giants of the sea – humpback whales, fin whales, and minke whales are frequently spotted in these waters. Our experienced naturalist guides will be with you every step of the way, providing fascinating insights into the behavior and biology of these incredible creatures. The tour also offers the opportunity to observe a variety of other marine life, including seals, porpoises, and a wide range of seabirds. Don't forget to bring your camera, as you'll want to capture these unforgettable moments.

Brewery-hop at brunch time—and visit several of Portland's best-known breweries and beer bars—on this small-group tour. With round-trip coach transit included, you can leave the driving to someone else and focus on enjoyment. Head to breweries that locals love, and enjoy in-depth tours and tastings, plus a light snack to help soak up those suds. By the end of the trip, feel newly immersed in one of the country's top craft beer scenes.

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.

Introducing Portland’s World of Flavors Walk highlighting hidden gems and great flavors that give Portland its cosmopolitan flair. Enjoy this walkable city with a big palate on our international journey, tasting locally sourced foods prepared with the recipes, customs and spices from other lands. On this 2.5-3 hour tasty romp through Portland’s historic Old Port and waterfront, you will enjoy the flavors while learning their food pathways and the owners journeys to Maine. Portland’s World of Flavor serves up a diversity of tastes and ethnicities in a compact area, packing a punch of flavors you will love. All tour experiences are highly educational and entertaining with trained, local guides.

Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.

⭐ Top-Rated Vacation Photoshoots 2025 We’re not just photographers, we’re storytellers capturing your holiday exactly as it feels. With over six years of experience photographing travellers around the world, our small team specialises in authentic, natural photography that truly reflects your trip. In Portland, we combine creativity with local knowledge to show you hidden gems, secret angles, and the best light. You’ll not only get beautiful, professional photos but also insider tips to make the most of your time here. We’re proud to be recognised among the top-rated photography tours of 2025, trusted by travellers worldwide for our relaxed style and stunning results.

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.

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.

Explore the charming coastal towns of Kennebunkport, York, and Portsmouth on this private day tour. Delve into the rich maritime history, enjoy stunning ocean views, and savor local flavors. With a personalized itinerary, this tour offers the flexibility to explore at your own pace, while an expert guide provides insights into each destination. Enjoy a relaxed atmosphere with included snacks, bottled water, and lunch to keep you energized throughout the day. - Private tour lasting approximately 7 to 8 hours - Customizable itinerary to suit your interests - Included lunch, snacks, and bottled water - Pickup from your location in an air-conditioned vehicle

With this small-group walking tour, you'll go beyond lobsters and lighthouses and get a look at the true Portland, Maine—across 400 years of history. Meander downtown and the Old Port, visiting hidden landmarks and learning about Wabanaki leaders and other people and events left out of the history books. Discover centuries of destruction, revival, underrepresented perspectives, and other elements that mainstream tours gloss over.

Set off on a refined culinary adventure through the serene waters of Casco Bay. Your journey begins at Portland Beer Hub, where you’ll gather before being escorted to the waterfront to board your boat. As you glide past the stunning coastline, savor freshly shucked oysters perfectly paired with crisp prosecco. Whether you’re toasting to a special occasion or simply indulging in a moment of pure relaxation, this experience blends Portland’s finest flavors with breathtaking coastal views—an unforgettable way to enjoy the best of land and sea.

Board the Elizabeth Grace for this exclusive one-of-a-kind experience. Whether you are a local or visiting from away, the stone fortresses built in the early 19th century in Portland Harbor are always captivating. They are imposing reminders of days not too far gone when the defense of our coastline required their presence. Despite their prominence, the forts are not easy to access for a variety of reasons, and most locals and visitors have never been to Fort Scammel, the only fort in the Harbor to see active combat. Fortunately, the owners of Fort Scammel have partnered with us to offer private tours of this incredible historic site. This is an experience NOT TO BE MISSED! Along the way, we’ll cruise past some of the other great sights in the bay, including the iconic lighthouses. GROUP OF 6 OR MORE? Please reach out to us about private charter options for the best experience possible! Our Fort Tour on a Private Island has a 4 PERSON MINIMUM to operate.

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.

Board your boat, the Elizabeth Grace, near the Portland ferry terminal and cruise around Portland Harbor at sunset, when Casco Bay and the coast of southern Maine are the most romantic. See lighthouses, historic forts, and stray groups of swimming seals and enjoy local craft beer from the boat. As the sun sets, turn toward Portland to see the town light up before returning to harbor.

Maine's Black community is small, but its history here goes back more than 400 years. On this guided tour, you’ll dive deep into Portland’s Black history, discovering how this community—national leaders, laborers, skilled workers, activists, and more—fought for freedom and equality and defined the state's path. From Frederick Douglass to lesser-known Black Yankees, there’s far more here than meets the eye, and with this tour, you’ll learn all about it.

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.

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 one of Maine’s most picturesque boating destinations—and enjoy a more up-close experience of the sights than most other tours offer—on this excursion by rigid inflatable boat. Departing straight from the marina, you’ll set off into the bay with just a small group for company. Spy the region’s many islands and lighthouses; look out for seals, porpoises, and other wildlife; and really immerse yourself in the maritime scenery.

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.

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

Start your experience with a guided tasting at a top local brewery, where you’ll sample a selection of expertly crafted beers. Then, gear up for an adrenaline rush as you test your skills with an hour of axe-throwing excitement—no experience needed, just a sense of adventure! After proving your aim, unwind and celebrate with another round of local brews at a second brewery, soaking in the vibrant flavors and atmosphere. Whether you’re a beer connoisseur, a thrill-seeker, or just looking for a unique outing, this experience promises fun, excitement, and great company!