The most comprehensive tour of Portland! Hop on board a trolley and relax as we show you around. The tour covers all of our most famous sights on the Portland peninsula. Towards the end of the tour, we make a 20-30 minute stop out... More

This 105 minute cruise offers guests a chance to relax and unwind as we make our way around the inner islands and lighthouses of the bay at dusk. Enjoy evening breezes and city lights on this fully narrated tour of Casco Bay. A gr... More

Explore the bustling inner harbor, Diamond Pass, and the main shipping channel to get close up views of civil war era forts and as many as 4 lighthouses that guide mariners into Portland Harbor.... More

- Portland's culinary culture is made up of many kinds of artisan food and beverage entrepreneurs from bakers, brewers and chefs to confectioners and more - wherever taste and creativity meet! - We combine a unique combination of ... More

Skip the city and head straight to the coast on this dedicated lighthouse tour of Maine’s best lighthouses. Explore three iconic beacons that have guided sailors for centuries, each offering a chance to delve into their rich his... More

Dive straight into Portland’s working waterfront—where the smell of the sea, and the bustle of the wharves, set the tone for an unforgettable walk through the city’s past. This immersive experience blends local history with... More

Meet Portland and the people—of all backgrounds and identities—whose wit and grit have made Maine's largest city what it is today. Your locally-raised guide will captivate you with extraordinary, exciting, and surprising stori... More

Curious about Portland's history with railroads, fires, wars, famous poets and Hollywood producers? Join us for a Walk Through Time! This tour begins on Commercial Street and continues for 2 hours through the historic Old Port, do... More

Step 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 bootlegge... More

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... More

This tour balances great food, stories, and a relaxed, local feel. Rather than rushing between stops or focusing only on tastings, this experience is designed to give you a genuine sense of Portland, how the food scene connects to... More

Discover the vibrant history of Portland’s Old Port on this engaging walking tour. Wander through cobblestone alleys and merchant blocks rich with stories of sailors, reformers, and immigrants. Learn about the Portland Freedom... More

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 sparkli... More

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... More

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 bustlin... More

This is a fully private Southern Maine coastal experience designed exclusively for your party (2–5 guests). No bus groups. No shared travelers — just your group, your pace, and a relaxed day along Maine’s scenic shoreline. V... More

Discover coastal New England on this private day tour from Portland, Maine to Massachusetts’ North Shore and Cape Ann. This thoughtfully curated experience blends grand seaside estates, medieval-style architecture, colonial hist... More

Explore the charm, history, and vibrant culture of Portland, Maine with this self-guided walking tour! Immerse yourself in the sights and sounds of this picturesque coastal city as you traverse the cobblestone streets of Old Port ... More

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 Wi... More

Hop on the “Guardians of the Harbor” trolley tour, a narrated journey with three lighthouse stops. Explore Portland’s maritime history and scenic beauty, disembarking at each location. First, visit Bug Light Park and the Li... More