Experience Portland’s Hidden Gems & Lighthouses with a Local Guide
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Discover Portland, Maine, on this engaging 1 hour and 45-minute historical tour led by a true local. From the cobblestone streets of Commercial Street to the scenic views of Casco Bay, you'll get an authentic look at the city’s rich maritime history and vibrant neighborhoods.
As a lifelong Portland resident and former college librarian, your guide shares stories, legends, and little-known facts that you won’t find in typical tourist guides. Expect a mix of historical landmarks, hidden gems, and lively commentary delivered with a good dose of Maine humor.
This tour isn’t just about sightseeing—it’s about experiencing Portland through the eyes of someone who loves and knows every corner of the city. Whether you're into architecture, history, or just want a fun way to explore, this experience offers something special for everyone.
Frequently asked questions
How long is the tour?
The tour lasts approximately 1 hour and 45 minutes.
What languages are available?
The tour is conducted in English.
What is the group size?
Groups are limited to up to 13 people.
Is the tour suitable for children and all fitness levels?
Yes, it’s suitable for all ages from infants to seniors, and accessible for all fitness levels.
What’s included in the tour?
You’ll have a knowledgeable, entertaining guide with 20 years of experience, and transportation in an air-conditioned vehicle.
Can I cancel if my plans change?
Yes. You can get a full refund if you cancel at least 24 hours before the scheduled departure. Cancellations within 24 hours are non-refundable, and the tour may be canceled due to bad weather.
Free cancellation
You can cancel for a full refund at least 24 hours before the scheduled tour time. Cancellations within 24 hours are non-refundable. Tours may also be canceled due to bad weather.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 1 hour 45 min
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Knowledgeable, entertaining guide with 20 years of experience showing Portland
- Air-conditioned vehicle
Itinerary
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Stop 1
Start at historic Commercial Street, the core of Portland's working waterfront, featuring original cobblestone and brick from the 1850s.
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Stop 2
View one of Portland's most beautiful granite buildings.
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Stop 3
Drive through Fort Allen Park for views of Casco Bay, the Calendar Islands, and historic memorials from the Civil War, Spanish-American War, and WWII.
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Stop 4
See Victorian-era homes along Eastern Promenade and enjoy sweeping views of Casco Bay, islands, and forts from Eastern Promenade Park.
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Stop 5
Observe the only remaining maritime signal tower in the U.S.
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Stop 6
Learn about the legends surrounding Portland's oldest cemetery, established in 1668.
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Stop 7
Explore Portland's lively downtown, Monument Square, and arts district.
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Stop 8
Admire the neo-Gothic architecture of Portland's historic cathedral built in 1869.
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Stop 9
Visit Portland’s oldest church and discover its historical significance.
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Stop 10
View the childhood home of Henry Wadsworth Longfellow, where he wrote some of his early poetry.
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Stop 11
Tour downtown Portland and its renowned Arts District.
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Stop 12
See the Portland Museum of Art and learn about its exhibits.
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Stop 13
View the statue of Longfellow, Portland’s famous poet born in 1807.
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Stop 14
Get an up-close look at Victoria Mansion, a prime example of 19th-century Italianate brownstone architecture.
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Stop 15
Enter Fort Williams Park and visit Portland Head Light, where you can explore the lighthouse and enjoy the coastal scenery.
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Stop 16
Walk up to Portland Head Light, the most photographed lighthouse in the country, and take in views of Maine’s rugged coastline.
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Stop 17
View Fort Preble, one of Casco Bay’s oldest forts, and learn about its history.
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Stop 18
Stop for photos at Spring Point Ledge Lighthouse and see the 900-foot-long breakwater connecting it to the shore.
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Stop 19
Enjoy panoramic views of Portland’s skyline from a scenic park across the bay.
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Stop 20
View the Liberty Ship Memorial and learn about shipbuilding during WWII.
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Stop 21
Take photos of Portland Breakwater Light, affectionately called 'Bug Light,' and learn about its history.
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Stop 22
See the statue honoring a famous movie director with ties to Portland.
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Stop 23
Explore the Old Port district, known for its eclectic shops, restaurants, and lively waterfront atmosphere.
Meeting point & pickup
Meet at the starting point
Please arrive at 96 Commercial Street, in front of the Casco Variety Store, at least 10-15 minutes before your tour departs. The tour begins at the bus parking spot next to the US Customs House, directly across from the store.
Open in Google MapsCancellation & confirmation
Free cancellation
You can cancel for a full refund at least 24 hours before the scheduled tour time. Cancellations within 24 hours are non-refundable. Tours may also be canceled due to bad weather.
- 100% refund if canceled at least 1 day before
- No refund if canceled within 24 hours
- Tour may be canceled for bad weather
Instant confirmation
Your booking is confirmed immediately after checkout.
From $74.00 per person
- Free cancellation
- Secure checkout with our booking partner
