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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
Sun 23 Feb
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You can choose the date already on the booking website
Starting at $57.00
Sun 23 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)
Gary65
Apr 2018
It happens every year... with three generations together for the holiday, what fun stuff could we do ALL together? The Real Portland tour easily accommodated the 10 of us including 3 car seats! As a local I must say Derek gives a great tour for anyone visiting from away AND those that live here. The fun facts he sent our way filled the gaps between the Forts and Lighthouses. I'll be sending my summer guests in August for sure.
Response from Host
Apr 2018
Thanks so much for the great review! It was a pleasure having a big group of all ages on board! It's always fun having local families come on a tour! I take pride in giving locals some fun facts they may not have known. Glad you were able to learn some new things, and I look forward to seeing your summer guests!
Jeff M
Apr 2018
I've been on a lot of tours - it's sort of my thing when I first visit a new city. I have to say that, without a doubt, The Real Portland Tour was the best one I have ever experienced! Derek provided an extremely informative tour that had everyone ooh-ing, "ayuh"-ing, and laughing all across town. We got to see three lighthouses and learned things I would never have expected about Portland and Maine in general; I'll never eat a donut again without thinking about Maine!
Response from Host
Apr 2018
Thanks so much for the great review! Really glad you had a nice time and that were able to learn some little known facts about my hometown! Hopefully we'll see you again in Portland sometime down the road!

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