Top Portland Tours, Sightseeing & Cruises - page 2

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.

Lighthouses are an iconic image associated with coastal Maine and Portland showcases some from the 1800s. Join this bicycling tour in Portland and see two of the city’s lighthouses from the 19th century. Follow quiet roads along South Portland’s coast to reach a small lighthouse called Bug Light, still in use today. Ride farther to Spring Point where a larger lighthouse awaits at the end of a long granite breakwater.

Experience the stunning beauty of Casco Bay on a personalized intimate (up to 6 guests per trip), public 2-hour powerboat cruise. Whether you're looking for a scenic sightseeing tour, an up-close encounter with Maine’s wildlife or a journey through the region’s rich maritime history, this exclusive charter is designed to provide an unforgettable adventure. Departing from the working waterfront, you’ll glide past busy wharves lined with lobster boats, ferries, and historic brick buildings that reflect Portland’s seafaring heritage. From the start, the mix of city energy and natural beauty sets the tone for an unforgettable journey on Casco Bay. Seals often bask on rocky ledges, ospreys and bald eagles soar overhead, and in the summer months, porpoises sometimes surface alongside the boat. Whether it’s spotting seabirds, breathing in the salty ocean air, or simply enjoying the thrill of the ride, a powerboat cruise from Portland offers both adventure and relaxation in equal measure.

Avoid the tourist traps and taste Portland, Maine's best donuts on a small-group walking tour. Follow your guide around the Old Port and sample several hand-picked donuts at award-winning bakeries with coffee or water included. Walk a scenic loop while hearing stories of Portland’s history and the invention of the donut. This tour offers a flavorful mix of food and local tales, perfect for food lovers and families alike.

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.

On this smartphone-guided adventure, you'll see Portland’s historic streets and discover its stories. Go at your own pace, anytime. The tour never expires. The tour is professionally produced with pro narration and music. It's location-aware walking step by step through the city. You’ll see the cobblestones streets, wharf street, Henry Wadsworth Longfellow’s home, stops on the underground railroad, city hall, exchange street, the lobster square, historic buildings, and the best spots to eat, including the best donut shop ever. Really, it’s that good. You'll hear the stories of Portland, Anna Kendrick’s favorite hangs, Longfellow’s history, stories of lighthouses, adventure, prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, colonial times, and much more.

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.

Step back in time to the bustling 18th Century port, where shipbuilding, trade, and whispers of strange occurrences at sea filled the air. Known for its picturesque waterfront, historic architecture, and vibrant arts scene, Old Port reveals its darker side at night. Supernatural tales include apparitions, psychic phenomena, and a sea serpent nicknamed Cassie.

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.

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.

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.

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.

With surrounding streams and ponds, beaches, man-made canals, and natural coves and inlets, Sebago Lake is ideal for exploring on kayaks. If you haven’t brought one with you, this rental can help you get on the water. After a safety briefing, take off from a private launch designed for easily getting in your kayak and into the water, and explore the natural beauty of the lake for about 4 hours.

Witness the stunning sunset over Casco Bay on this two-hour public powerboat cruise aboard the classic Maine-built vessel, Avelinda. As the sun sets, enjoy picturesque views of iconic lighthouses like Portland Head Light and serene islands such as Peaks Island. With a maximum of six guests per boat, relish an intimate experience while keeping an eye out for local wildlife like seals and seabirds. Captains with extensive local knowledge share tales of the region's rich history, making this cruise a perfect way to unwind and soak in the beauty of Maine's coast. Open to all ages, it’s a memorable outing for families and couples alike. - 2-hour scenic sunset cruise through Casco Bay - Maximum of 6 guests for an intimate experience - Spot local wildlife and iconic Portland lighthouses - Knowledgeable captains share local history and ecology

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.

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.

All our tours take place in a comfortable vehicle with a local driver-guide and can be tailored to your pace. This private tour is done in our larger passenger van that can take up to 12 passengers. We’re happy to customize the experience to match your interests. This particular tour covers all the major sights in Portland, followed by a visit to the South Portland lighthouses, including admission to Fort Williams Park to see the Portland Headlight. After exploring Portland, you'll journey down the highway to Kennebunkport, a charming coastal village that served as the summer retreat for former President George W. Bush and his family. While we have a standard route, as a private tour, we can personalize the itinerary to suit your preferences.

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.

Experience historic architecture, harbor views, and rich seaside culture with this driving tour of Portland, Maine! Cross the cobbled streets of Old Port, chock full of shops, restaurants, and bars, all complemented by the sparkling bay. Dive into the city’s long and embattled history at a church still sporting British cannonballs. See iconic Maine lighthouses and visit pristine beaches. Portland may be a small city, but it packs a big punch! Purchase one tour per car, not per person. Everyone listens together! 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.

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.

Explore the lighthouses of the South Portland Greenbelt Pathway by bicycle with this guided tour. You'll visit Bug Light, Point Ledge Light, and Portland Head Light with a local guide. You'll also have the chance to stop at a local food truck for a lunch of lobster rolls before returning to your starting point.

Some cities are best seen from a car window. Portland, Maine is not one of them. On this fully private e-bike tour, it's just your group, a local guide, and five hours of spectacular coastal scenery — with a Maine lobster roll along the way. Ride through the Old Port's cobblestone waterfront and fishing piers. Climb to Fort Allen Park for sweeping Casco Bay views. Cruise the Eastern Promenade before crossing to South Portland to walk the breakwater to Bug Light, designed by the architect of the U.S. Capitol dome. Continue to Spring Point Ledge — the only lighthouse of its kind you can reach on foot — then Portland Head Light, commissioned by George Washington in 1791. Finish on the Western Promenade, a hidden hilltop park with views to the White Mountains that most visitors never find. Lunch is a fresh Maine lobster roll at a waterfront spot worthy of the occasion. No strangers, no set pace — just your group and the best of coastal Maine.

The hour just before sunset is the best time for stand-up paddling on the waters of Casco Bay. The sky tends to explode with color and the seas often become glassy and calm. This trip involves a leisurely paddle just far enough along the waterfront or into the islands to enjoy a panoramic view of the sun setting over the city as we paddle back to the East End Beach. This two-hour tour is designed for people of all experience levels — including those new to stand-up paddling.

100% Private Charter for Groups up to 15 — Flat Rate Pricing This exclusive 2-hour boat tour is designed for private groups seeking an authentic, intimate experience on Casco Bay. Unlike crowded public cruises, your group of up to 15 guests will enjoy the full comfort and charm of one of our classic wooden vessels—all to yourselves. Cruise past iconic lighthouses, historic granite forts, and stunning stretches of Maine’s coastline, with opportunities to spot harbor seals, seabirds, and other local wildlife along the way. Whether you’re celebrating a special occasion or simply gathering with friends, this charter offers a personalized, relaxed way to experience the best of coastal Maine. Feel free to bring your own food—we provide all the glassware, plates, and utensils you’ll need. Local craft beer, wine, and other beverages are also available for purchase onboard. Due to our liquor license, we do NOT permit outside alcoholic beverages on board.