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The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

Overview
Welcome to my hometown! Hop aboard for an authentic 90 minute sightseeing tour of Portland and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, ME.

Get an insider’s look at the current happenings and rich history of my hometown. We’ll go where other tours go, and then I'll take you places other tours don't - you'll see hidden gems and learn little known facts about Portland and the great state of Maine that only a real local knows!

As a college librarian I'm always researching the hidden history of Portland, while at the same time keeping on top of what's new in town and visiting as many local establishments that I can. I take pride in representing this city, and providing an informative and entertaining tour, delivered with a true Mainer's sense of humor.

This is The Real Portland Tour!

Check my website for a complete listing of tour days, times, and availability.
City: Portland
Mon 24 Feb
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You can choose the date already on the booking website
Starting at $57.00
Mon 24 Feb
Starting at $57.00
Make a reservation
What's Included
Knowledgeable, entertaining guide with 20 years experience giving tours of his hometown of Portland.
Air-conditioned vehicle
Additional Info
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Unfortunately no pets/animals of any kind can be accommodated on board. Thank you for your understanding.
  • The tour does not pickup/drop off at hotels, and it does not pickup/drop off at the cruise ship terminal. Everyone has to be at the tour starting point ready to board at least 10-15 minutes prior to the scheduled tour time.
  • Wheelchairs, walkers, and luggage do not fit in the van.
  • The tour vehicle is a 13 passenger, high roof Ford Transit van. The tour often sells out, so you will be riding with a total of 13 people in the van.
  • Hand sanitiser available to travellers and staff
  • Transportation vehicles regularly sanitised
  • Guides required to regularly wash hands
  • Regular temperature checks for staff
  • Unfortunately no pets/animals of any kind can be accommodated on board. The tour does not pickup/drop off at the cruise ship terminal, and it does not pickup/drop off at hotels. Wheelchairs, walkers and luggage do not fit in the van. You'll be riding with 13 people in the high-roof Ford Transit van.
What To Expect
1
Commercial Street
We start at historic Commercial Street, the heart of Portland's working waterfront. See original cobblestone and brick that was laid in the 1850s.
2
United States Custom House
See one of the most beautiful granite buildings in all of Portland.
3
Fort Allen Park
We'll drive through Fort Allen Park and get a majestic view of Casco Bay and its Calendar Islands. Also get up close views of memorials from the Civil War, Spanish American War, and WWII located in the park.
4
Eastern Promenade Trail
You'll see the Victorian era homes once owned by sea captains and merchants that line the Eastern Promenade, as well as Eastern Promenade Park which offers endless views of Casco Bay, islands, and forts.
5
Portland Observatory
We'll get a great view of the only remaining maritime signal tower in the U.S.
6
Eastern Cemetery
Hear about the legends and lore regarding the oldest cemetery in Portland, first established in 1668.
7
Congress Street
One of the busiest streets in all of Maine, we'll see Portland's eclectic downtown, Monument Square, and arts district.
8
The Cathedral Of The Immaculate Conception
The neo-Gothic architecture of this cathedral built in 1869 dominates the skyline of Portland.
9
The First Parish Portland Unitarian Universalist
This church is the oldest in Portland, and you'll learn about its rich history.
10
The Wadsworth-Longfellow House
See the home where Henry Wadsworth-Longfellow grew up and wrote his early poetry.
11
Arts District
We'll tour the center of downtown Portland, and its highly acclaimed Arts District.
12
Portland Museum of Art
See one of the finest art museums in New England, and learn about its exhibits.
13
One Longfellow Square
See the statue of Henry Wadsworth Longfellow, born in Portland in 1807.
14
Victoria Mansion
Get an up close view of the Victoria Mansion, the finest example in the country of a 19th century Italianate brownstone.
15
Fort Williams Park
We enter one of the most beautiful parks in the state, Fort Williams Park, and drive to Portland Head Light (located in the park) where you will be let off to explore.
16
Portland Head Light
This iconic lighthouse located within Fort Williams Park is the most photographed lighthouse in the country. Walk right up to the lighthouse, explore Fort Williams Park, and take in the views of Maine's rugged, rocky coastline.
17
Fort Preble
Get an up close view of Fort Preble (one of the oldest forts in Casco Bay) and learn about its storied history.
18
Spring Point Ledge Lighthouse
Get out for a photo of Spring Point Ledge Lighthouse, and its 900 foot long breakwater connecting it to the shore.
19
Bug Light Park
Enjoy panoramic views of the Portland skyline from this beautiful park that sits directly across the bay from Portland.
20
Liberty Ship Memorial
Get an up close view of the Liberty Ship Memorial, and learn about the thousands of shipbuilders who worked here during WWII.
21
Portland Breakwater Lighthouse
Get a photo of Portland Breakwater Light (affectionately called "Bug Light" because of its small size).
22
John Ford Statue
Get an up close view of this statue dedicated to one of the most distinguished movie directors in history, and learn about his connections to his hometown of Portland.
23
Old Port
See the center of the bustling downtown/waterfront district known as the Old Port. Learn the history of this vibrant area of Portland that is home to countless eclectic shops, businesses, and world class restaurants and bars.
Show 20 more stops
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Traveler Photos
Reviews (770)
oldtrout52
May 2018
Ben’s tour totally fulfilled his promise of showing us the Real Portland ! We had a great time this morning. He’s a relaxed, humorous and very well informed guide to the rich history of Portland ( as a fellow librarian I would expect nothing less!) and we saw all sorts of nooks and crannies as well as the main sights and of course the 3 lighthouses. Highly recommended.
Response from Host
May 2018
I'm so glad you enjoyed the tour! It was a pleasure having you on board! It's always a treat to have a fellow librarian on the tour! Thanks so much for the great review. It must have got lost in translation that my name is actually Derek, not Ben! Maybe it was my Maine accent! No worries, I hope you have a great rest of your trip!
amandabharvey
May 2018
I did this tour as part of a bachelorette party, and we had the entire bus to ourselves! It was perfect for a cold and rainy day, since we got to stay warm and dry while seeing parts of Portland that we hadn't visited yet. It's a compact city so you're able to see a lot in a short amount of time. Derek was super knowledgeable about the history of the city, and full of fun facts and puns! As others have said, the rap is amazing!! We only got the short version, unfortunately, be sure you get the unabridged one. I highly recommend this tour from a REAL Portland native.
Response from Host
May 2018
Thanks so much for the great review! I had a lot of fun giving a tour to your group! I take pride in showing folks the REAL Portland! Glad you enjoyed the rap, and next time you're in town I'll make sure to give you the unabridged version!
Leah B
May 2018
My coworker referred us to TRPT for my best friend's bachelorette, so we decided to rent out the entire bus for her party!! We had an amazing time. Derek was punctual, factual and punny. All the best characteristics of a tour guide, giving us a real local flavor of Portland outside of the downtown area where we had spent the entire weekend. It was perfect for a slightly rainy day because his van is very comfortable and cozy. Highly recommend this tour for visitors and don't forget to ask him about his Portland rap!! Too good. ;)
Response from Host
May 2018
Thank you for the review! It was a pleasure having your group on board! I'm glad you chose Portland as your bachelorette party destination, and that The Real Portland Tour was a part of the festivities! My vehicle is great for groups looking for a private tour, and I'm happy it worked out so well! Happy to hear you enjoyed my rap too!! Hopefully we'll see you all again!

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