Embark on a driving tour of Portland, Maine and immerse yourself in its historic seaside culture. Explore charming architecture, harbor views, and iconic lighthouses. Book now!
Embark on a driving tour of Portland, Maine and immerse yourself in its historic seaside culture. Explore charming architecture, harbor views, and iconic lighthouses. Book now!
- West Street - The Maine Medical Center houses the Barbara Bush Children’s Wing. Mrs. Bush, the wife of the 41st president and mother of the 43rd president, spent much of her life in Kennebunkport, Maine, 30 miles south of Portland. She passed away in 2018. Mrs. Bush made significant contributions by raising funds for the treatment of children with…
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West Street - The Maine Medical Center houses the Barbara Bush Children’s Wing. Mrs. Bush, the wife of the 41st president and mother of the 43rd president, spent much of her life in Kennebunkport, Maine, 30 miles south of Portland. She passed away in 2018. Mrs. Bush made significant contributions by raising funds for the treatment of children with serious illnesses, and her legacy is honored in the Children’s Wing of the Maine Medical Center.
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Victoria Mansion - This is the Victoria Mansion, constructed by Ruggles Morse in 1858. It is considered “the best standing example of Victorian art, architecture, and decoration.” Named “Victoria Mansion” after Britain’s Queen Victoria, it was built as his summer residence.
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The Danforth - On the left, observe the vibrant brick rowhouses. Originally built for the servant class, these rowhouses have now become luxurious and expensive condominiums. Following numerous fires, brick became the primary building material throughout the city, replacing wood.
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Commercial Street - Portland’s Harbor, the body of water you just sailed on, is a “deep water” port that generally does not freeze over in winter. The Gulf of Maine experiences strong tides, which mix the water column and bring deeper, warmer water to the surface along the coast.
Note: The tour spans over 12 miles, includes more than 33 audio stories, and takes approximately 1-2 hours to complete.
Purchase once and enjoy for a year! Perfect for extended visits and return trips over the next 12 months.
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One Longfellow Square - On the right side of the coach, you’ll pass the home of Neal Dow. A former Portland mayor, Neal Dow is recognized as the father of American Prohibition. In 1851, then-Mayor Dow implemented a statewide prohibition—banning the sale and consumption of intoxicating beverages—that served as a model for National Prohibition.
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Arts District - This is “Portland’s Arts District,” featuring numerous independent art galleries, working studios, coffee houses, and restaurants. Ahead on the right is the Portland Art Museum.
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Brown Street - Just past the unremarkable building on the right—the gray/brown Maine Historical Society headquarters—is the Wadsworth Longfellow House. It’s the brick building set slightly back from the road on the left. This is where the poet grew up. Built after the Revolutionary War by Peleg Wadsworth, a Revolutionary War General and the grandfather of Henry Longfellow, it’s the oldest brick house in Portland.
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Temple Street - On our left is the 1st Parish Unitarian Universalist Church, the oldest church in Portland. This is the second building to house this congregation.
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Portland City Hall - On the left is Portland’s City Hall, a stunning building for a small city. This is the third City Hall building on this site, as the first two were destroyed by fire.
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Franklin Street - The tall brick and concrete building to your left is the Franklin Tower, built in the 1970s. It stands as the tallest building in the state of Maine at 16 stories.
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Eastern Cemetery - Here is Portland’s Eastern Cemetery, the oldest cemetery in the city. Some headstones date back to 1768. The oldest markers were wooden and were lost to fires.
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Portland Observatory - Let’s revisit the 1800s, when ships entering Portland Harbor were not visible from the docks until they rounded the point of land at Spring Point Ledge and were nearly in the harbor.
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Waterville Street - Notice the “flattop triple-decker” tenement housing style, typical in New England, built from the 1880s to the 1920s.
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Munjoy Street - Off to the right is Portland Harbor, part of Casco Bay, an inlet on the southern coast of the Gulf of Maine. The City of Portland is located along its southern edge, with the Port of Portland within.
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Casco Bay - If you look over your right shoulder, you’ll see the landmass with the oil tanks, which is the City of South Portland.
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Eastern Promenade Trail - The Eastern Promenade is a wonderful space where Portlanders enjoy the pleasant weather and sea breezes. At the foot of the Eastern Prom is a small beach called East End Beach.
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Walnut Street - After the British destroyed the city in 1775, Portland’s city leaders decided to build a fort. The green space on the right is the result of that decision.
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Fore Street Restaurant - You may recall our earlier discussion about the streets in Old Portland, named for their proximity to the water: Fore St, Middle St, and Back St.
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Casco Bay Bridge - As we continue our drive in Portland, we will head to the Casco Bay Bridge. The bridge spans Casco Bay, connecting the City of Portland with the City of South Portland.
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Meetinghouse Hill - As we travel through the City of South Portland, we approach Meetinghouse Hill. It presents a quintessential New England scene with a cemetery on the left, a Civil War statue on the right, and a beautiful church behind the statue.
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Fort Williams Park - We are now entering Fort Williams Park, where you’ll notice several military installations.

- Easy-to-use app: download Action’s Tour Guide App onto your phone
- Great value: purchase per car, not per person. More affordable than bus or guided tours!
- Engaging storytelling: Uncover unique tales and thrilling history for a memorable journey!
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Perfect narrator: nothing can beat listening to a great voice. Proven with tons of rave reviews!
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- Easy-to-use app: download Action’s Tour Guide App onto your phone
- Great value: purchase per car, not per person. More affordable than bus or guided tours!
- Engaging storytelling: Uncover unique tales and thrilling history for a memorable journey!
- Perfect narrator: nothing can beat listening to a great voice. Proven with tons of rave reviews!
- Offline maps: no signal, no problem! Works perfectly without cellular or wifi.
- Comprehensive route and stops: See it all, miss nothing, leave no stone unturned!
- Go at your own pace: Start anytime, pause anywhere, enjoy breaks for snacks and photos freely!
- Hands-free: audio stories play on their own based on your location. Easy to use!
- Attraction passes, entry tickets, or reservations
- Attraction passes, entry tickets, or reservations
Discover the charm of historic architecture, stunning harbor views, and vibrant seaside culture with this driving tour of Portland, Maine! Navigate the cobblestone streets of Old Port, teeming with shops, restaurants, and bars, all set against the backdrop of the glistening bay. Explore the city’s storied past at a church that still bears British…
Discover the charm of historic architecture, stunning harbor views, and vibrant seaside culture with this driving tour of Portland, Maine! Navigate the cobblestone streets of Old Port, teeming with shops, restaurants, and bars, all set against the backdrop of the glistening bay. Explore the city’s storied past at a church that still bears British cannonballs. Marvel at iconic Maine lighthouses and enjoy pristine beaches. Though Portland is a small city, it offers a wealth of experiences!
Purchase one tour per vehicle, not per individual. Everyone can listen together!
After booking, check your email or text messages 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 specified starting point.
Buy once and use it for a whole year! Perfect for extended stays and return visits over the next 12 months.
Please note, this is not an entrance ticket. Verify opening hours before your visit.
- How To Access: After booking, you’ll get an email and text with setup instructions and password (search “audio tour” in emails and texts). • Download the separate tour app by Action • Enter the password sent by email and text. • MUST download the tour while in strong wifi/cellular. • Works offline after download.
- How to start touring: Open Action’s separate audio tour guide app once onsite. • If there is just one tour, launch it. • If multiple tour versions exist, launch the one with your planned starting point and direction.
- Go to the starting point No one will meet you at the start. This tour is self-guided Enter the first story’s point and the audio will begin automatically Follow the audio cues to the next story, which will also play automatically. Enjoy hands-free exploring. If you face audio issues, contact support. Stick to the tour route & speed limit for the best experience.
- Travel worry-free: Use the tour app anytime, on any day, and over multiple days. Start and pause the tour whenever you like, taking breaks and exploring side excursions at your own pace. Skip anything you don’t care about or explore bonus content for everything that interests you
- Savings tips: Driving tours: purchase just one tour for everyone in the car
- Buy once, use for one year! Ideal for extended visits and return trips over the next 12 months.
- Audio Setup: Connect your phone to your car’s stereo system using Bluetooth, USB, or AUX. For the best experience, consider using headphones for walking tours. Audio playback is compatible with Apple CarPlay, with navigation features coming soon. Support for Android Auto is also on the way.
- For the best experience, please use an iPhone running iOS 15 or later, an Android device running version 9 or later, or an iPad/tablet with GPS and cellular connectivity, as these are recommended for navigation.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.