Activities and Tours in Portland
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97 activities & tours found
Guided RIB Boat Adventure of Casco BayDepart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses and our unique 14-passenger RIB boat is suited to tour the region while everyone gets a front-row seat so you can see and experience more of it.
Learn about Portland’s nautical history, view wildlife like seals, harbor porpoises, and sea birds, and stop for photos at quintessential sights like all four...
1 hour 30 minutes
Free Cancellation
$75.00View
Two Hour Lighthouse Bicycle Tour from South Portland-MellowOur 2-Hour tour leaves at 9 am or 3 pm and follows the scenic South Portland Greenbelt Pathway to two local lighthouses. The first stop on the tour will be Portland Breakwater Light, also known as "Bug Light" and then the tour will continue to Spring Point Ledge Light, located near historic Fort Preble, before returning to the bike shop.
2 hours
Free Cancellation
$75.00View
Likely to sell out
Portland History Walking TourStep back in time and immerse yourself in the rich history of Portland, Maine, with this engaging walking tour through the heart of the city. Your expert guide will lead you through Portland’s charming streets, sharing stories of its colonial past, the rise of its maritime industry, and its key role in American history. As you stroll through the Old Port and waterfront, you’ll discover historic landmarks, cobblestone streets, and unique architecture that reflect Portland’s vibrant heritage. This...
2 hours
Free Cancellation
$50.00View
Sunset & Scenic Private Boat Tour of Portland & Casco BayPrivate Casco Bay Cruise – Up to 5 Guests
Experience the beauty of Maine’s coast on a private 2-hour tour through the scenic Casco Bay islands. This intimate charter is perfect for small groups looking to explore hidden coves, spot local wildlife, and soak in the iconic charm of the Maine coastline.
Departures daily at 10 AM, 4 PM, and our most popular sunset cruise at 6:30 PM.
2 hours
Free Cancellation
$650.00View
Half Day Kayak Rental on Sebago LakeThe Must-Do Sebago Lake Experience!
Explore the panoramic views of Sebago Lake with our unbeatable rental package! With our EZ Launch system, you'll enjoy easy access to launch right from our private site nestled between Panther Run stream and the north end of Sebago Lake. With your fitted life jacket, paddle and map in hand, you'll have endless opportunities to discover the lake's hidden coves, beaches, islands and wildlife.
Paddle along meandering streams before emerging into Sebago's scenic...
1 hour to 4 hours
Free Cancellation
$44.00View
Portland Wine Walking TourDiscover the best of Portland’s vibrant wine scene with the Portland Walking Wine Tour. Perfect for wine lovers and curious explorers alike, this leisurely walking tour takes you through the city’s charming streets to three handpicked wine-centric shops. At each stop, you’ll indulge in curated tastings of exceptional wines, from local Maine favorites to acclaimed international selections. Your expert guide will enrich your experience by sharing captivating stories about each wine’s origins, tast...
2 hours 30 minutes
Free Cancellation
$120.00View
Bootleggers, Bosses & BloodshedStep into the shadows of Portland’s past on this thrilling true crime tour, where secrets lurk behind historic facades and cobblestone streets whisper tales of corruption, violence, and vice. From ruthless mobsters and bootleggers to power-hungry bosses and shocking scandals, this tour unveils the darker side of Maine’s largest city. Walk the very streets where speakeasies thrived, deals were made in the dead of night, and blood was spilled in the name of power. Led by expert guides, this journe...
2 hours
Free Cancellation
$50.00View
Sunset Lighthouse Cruise Along Casco BayEmbark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your favorite wine or beer and a delicious meal, and unwind as we cruise through the serene waters of Casco Bay. Journey aboard Ruth—a charming 39-foot classic picnic-style tour boat crafted in 1935 at Handy Boat in Falmouth, Maine. Don't miss out on this unique sunset experien...
1 hour 30 minutes
Free Cancellation
$67.00View
Sunset Tour by Kayak on Sebago Lake MaineDiscover the serene beauty of water-carved bends and meandering streams, where local wildlife thrives against a backdrop of rustic charm. As we embark on our journey, we'll navigate the gentle twists and turns of a meandering stream, revealing the untouched beauty. Let the tranquil waters carry you along as you immerse yourself in the sights and sounds of the natural world.
Throughout the tour, our knowledgeable Registered Maine Guide will regal you with captivating stories, bringing the scene...
2 hours
Free Cancellation
$59.00View
Likely to sell out
Sea Kayak to an Island Tour in Casco BayLearn the basics of sea kayaking on land before launching at Mere Point in Brunswick for a leisurely 3 hour morning tour of Northwest Casco Bay! Often we paddle south to the end of Mere Point for a photo op and then on to visiting an island for a stretch break, snacks, and shoreline exploring. Then we paddle back on a different route close to an island to our launching point. Your Master Maine Guide will share history of the area while adapting the tour to paddling conditions and participants a...
3 hours
Free Cancellation
$89.00View
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