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Peek at Portland: Open-Air Trolley City Tour
4.7
151 Ratings
Portland
The Peek at Portland is the only open-air trolley tour in the city and provides a comprehensive 60-minute commentary of Portland’s most renowned landmarks and diverse districts, while still granting you ample time to delve into the city independently.
The Peek at Portland is the only open-air trolley tour in the city and provides a comprehensive 60-minute commentary of Portland’s most renowned landmarks and diverse districts, while still granting you ample time to delve into the city independently.
Duration:
1 hour
Cancellation:
24 hours
Highlights
- Victoria Mansion - American residential architecture highlight
- Portland Observatory - Historic monument that resembles a lighthouse
- Portland Museum of Art - Largest and oldest public art institution in the U.S. state of Maine.
- The Wadsworth-Longfellow House - Oldest standing structure on the Portland peninsula and the childhood…
- Victoria Mansion - American residential architecture highlight
- Portland Observatory - Historic monument that resembles a lighthouse
- Portland Museum of Art - Largest and oldest public art institution in the U.S. state of Maine.
- The Wadsworth-Longfellow House - Oldest standing structure on the Portland peninsula and the childhood home of American poet Henry Wadsworth Longfellow.
- Eastern Promenade - Sweeping views of Casco Bay and home to the Munjoy Hill neighborhood

What's Included
- narrated tour
- narrated tour
Additional Information
- Strollers can be stored at our tour booth while on tour.
- Strollers can be stored at our tour booth while on tour.
Location
170 Commercial St
Commercial Street
The middle window in in a blue and white kiosk booth marked Long Wharf on top.
Cancellation Policy
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.
Customer Ratings
4.7
(151 Ratings)
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J9332lzmichaelw
Jul 8, 2025
Great tour of the city - Great trip with Barry! Saw some great sites and got some behind the scenes history of Portland. Would definitely recommend for others.
Review provided by Tripadvisor
Dana_b
Jun 25, 2025
Knowledge - Very nice, gained a lot of historical knowledge of the city. The tour guide was funny and clever. Got a true understanding of the area.
Review provided by Viator
Timwyg
Jun 24, 2025
Great tour! Awesome driver! - We took the Portland Sightseeing Trolley tour on our recent trip to Portland. Wendy Lee was our driver, and she was amazing! Not only did she keep us safe driving through the busy streets of town, but she was also extremely knowledgeable about the sights and history of the city! Humor? Lot of it! Fun? Definitely! Would recommend to anyone visiting Portland.
As a note, take a second tour with Portland Discovery Land & Sea Tour and mention your first tour for a discount.
Review provided by Tripadvisor
Maps50638224871
Jun 16, 2025
Fabulous time! - Our group of 4 girlfriends really loved our Trolley Tour with Wendy! We learned so much about Portland & can’t wait to return to stroll around some of the wonderful areas Wendy pointed out to us! She made it a fun time as well! We all Wholeheartedly recommend doing the tour & hopefully you get Wendy Lee as your guide!
Review provided by Tripadvisor
957cherylv
Jan 19, 2025
Talented Trolley Driver/Narrator Brings Portland to Life - We were so very fortunate to make a quick decision to book Portland Sightseeing Trolley Tours for our self-directed off-cruise ship excursion. We were doubly fortunate to have Wendy Lee as our Driver/Narrator for what we learned was the last tour of the season!
From the moment my friend and I stepped onto Wendy Lee's trolley, we knew we were in for a unique experience. Her vivacity, humor and all-around joie de vivre were so refreshing we immediately felt we'd known her all our lives. Furthermore, her vast knowledge of the history of Portland felt like a rare and wonderful history lesson taught by a consummate teacher, performer and obvious fan of her home city.
The tour was wonderfully capped off by Wendy's suggestion that we go to Gilbert's when we mentioned wanting Maine chowder. She told us to ask for the chowder "flight" which wasn't on the menu. Wow - so many kinds of chowder and all delicious! This was a special thing that only a long-time resident would know about, and we were so grateful that she shared it with us. Another fantastic Portland experience!
I think this excursion was the highlight of our New England cruise. Portland Discovery Tours is indeed fortunate to have a treasure like Wendy Lee "onboard" to entertain, enlighten and engage travelers about your beautiful, historic city. (We especially loved the "Dessert of the State" quiz!)
*Please convey to Wendy that we will definitely be returning to Portland to explore more of your wonderful city. When we do we hope to see her in her trolley, and say hi!
Best,
Cheryl (PA)
Louella (CT)
Review provided by Tripadvisor
C_s
Oct 5, 2024
Great look at Portland - Tour guide made the trip both interesting and fun. Provided interesting facts for multiple spots along the way
Review provided by Viator
Cornelisrebeccak
Oct 3, 2024
Trolley tour - 10 out of 10 - This was a great tour and well worth the experience. Our trolley driver Wendy did a great job giving us a lot of information sprinkled with humor. It was a wonderful way to see the city and we saw and learned more than we would have just walking around ourselves.
Review provided by Tripadvisor
James_n
Oct 2, 2024
Portland in a Trolley Bus - Great trip around Portland City in a trolley bus. Lots of historical information provided by our lady driver who also had a great sense of humour. We also had a visit to the Portland Lighthouse.
Review provided by Viator
Bob
Oct 2, 2024
Portland by Trolley - The driver provided lots of interesting information with a sense of humor. He also spoke very plainly and was easy to hear especially since I'm hard of hearing.
Review provided by Tripadvisor
Meridth2022
Oct 1, 2024
Good way to see Portland and lighthouse - Nice your, explained details well and plenty of time to stop for lighthouse self viewing and photos. Does accept walk ups if you can’t get preferred reservations online,
Review provided by Tripadvisor
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