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

Discover Portland’s hidden gems and rich history with a local guide. Explore 3 lighthouses and uncover secrets only a true Mainer knows.

Duration: 1 hour, 45 minutes
Cancellation: 1 day learn more
Highlights
  • 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.
  • United States Custom House - See one of the most beautiful granite buildings in all of Portland.
  • 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.
  • 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.
  • Portland Observatory - We’ll get a great view of the only remaining maritime signal tower in the U.S.
  • Eastern Cemetery - Hear about the legends and lore regarding the oldest cemetery in Portland, first established in 1668.
  • Congress Street - One of the busiest streets in all of Maine, we’ll see Portland’s eclectic downtown, Monument Square, and arts district.
  • The Cathedral Of The Immaculate Conception - The neo-Gothic architecture of this cathedral built in 1869 dominates the skyline of Portland.
  • The First Parish Portland Unitarian Universalist - This church is the oldest in Portland, and you’ll learn about its rich history.
  • The Wadsworth-Longfellow House - See the home where Henry Wadsworth-Longfellow grew up and wrote his early poetry.
  • Arts District - We’ll tour the center of downtown Portland, and its highly acclaimed Arts District.
  • Portland Museum of Art - See one of the finest art museums in New England, and learn about its exhibits.
  • One Longfellow Square - See the statue of Henry Wadsworth Longfellow, born in Portland in 1807.
  • Victoria Mansion - Get an up close view of the Victoria Mansion, the finest example in the country of a 19th century Italianate brownstone.
  • 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.
  • 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.
  • Fort Preble - Get an up close view of Fort Preble (one of the oldest forts in Casco Bay) and learn about its storied history.
  • 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.
  • Bug Light Park - Enjoy panoramic views of the Portland skyline from this beautiful park that sits directly across the bay from Portland.
  • 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.
  • Portland Breakwater Lighthouse - Get a photo of Portland Breakwater Light (affectionately called “Bug Light” because of its small size).
  • 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.
  • 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.
What's Included
  • Knowledgeable, entertaining guide with 20 years experience giving tours of his hometown of Portland
  • In-vehicle air conditioning
Additional Information

Welcome to my birthplace! Join us for a genuine 90-minute exploration of Portland and its 3 fabulous lighthouses guided by an expert who hails from this very city of Portland, ME.

Take a peek behind the scenes of my birthplace’s thriving scene and deep-rooted tradition. We’ll venture where usual tours take you, and then I’ll escort you to charming spots that aren’t included in mainstream tours. You will discover secret treasures and little-known trivia about Portland and the magnificent state of Maine that only a true native can reveal!

As a college librarian, I perpetually delve into Portland’s clandestine past, while keeping my finger on the pulse of what’s fresh in our town and patronizing as many local businesses as possible. Representing my city fills me with pride, and I aim to provide an enlightening and engaging excursion, peppered with a quintessential Mainer’s wit.

This is The Authentic Portland Tour!

For a comprehensive schedule of tour dates, timings, and open slots, visit my website.

  • The tour is in Portland, MAINE. Unfortunately no pets/animals of any kind can be accommodated on board.
  • 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.
  • Please double check the month, day, and time of your booking to make sure it is accurate, as some folks make mistakes when booking online and choose the wrong date.
Location
96 Commercial St
Commercial Street
Please arrive at 96 Commercial Street (in front of the Casco Variety Store) at least 10-15 min before your tour time. The tour departs from the tour bus parking spot next to the US Customs House, which is located directly across the street from the Casco Variety Store.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(1150 Ratings)
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Richard_r
Sep 9, 2024
“Must do” for first-timers in Portland! - This was our first visit to Portland, and the tour was the perfect introduction. Our guide, Derek, was excellent, knowledgeable, and personable. A great tour on a sunny, glorious day!
Review provided by Viator
Tamalas_r
Sep 6, 2024
Awesome tour, very informative & interesting! - The whole tour was very informative and interesting. Derek gave us a great overview of Portland’s history. Loved his little jokes and lively attitude. Appeared to have a lot of love for his hometown and state!
Review provided by Viator
Cathy_r
Sep 4, 2024
Portland in 90 minutes - We had a good time. The tour guide was very knowledgeable. He was a local and shared a lot no one else would have. Suggested restaurants and interests to see. Pick up and drop off was right on! Nice clean van. You can’t go wrong with this tour, 90 minutes.
Review provided by Viator
Matthew_c
Sep 4, 2024
Good Times in Portland - My whole family had a great time on this tour. Derek was a great tour guide. We learned a lot and laughed a lot as well. Portland is a beautiful city and I felt we really got to know the lay of the city from this tour. Highly recommend.
Review provided by Viator
Karen652014
Sep 3, 2024
Best Portland Tour - Derek was an amazing tour guide. My mom and I have traveled around the world and have taken many tours through the years. This tour guide is one of our favorites. He is extremely knowledgeable with great energy and sense of humor. He keeps the information constantly flowing and all his guests engaged. Highly recommend this tour. It is the real tour of Portland -accent and all.
Review provided by Tripadvisor
Michael_t
Sep 3, 2024
Beautiful Informative Tour - This was a wonderful tour! He made our trip so amazing. He was very accommodating and knowledgeable about the history of the area. We really enjoyed the tour and would highly recommend!
Review provided by Viator
Vpate1
Sep 1, 2024
Wonderful adventure - We had a fantastic time on this tour. Eric was very knowledgeable and had a great personality. We were only there one day and this was the perfect tour to get a little history and see the 3 lighthouses up close in the Portland area. He also gave us some great places to eat lunch. We highly recommend this tour. It was very affordable as well!
Review provided by Tripadvisor
Rusteesticker
Sep 1, 2024
Great tour! - As a solo traveler, this was the perfect tour for me. Derrick was very entertaining and knew so much about his hometown, Portland. The van was clean, comfortable, and a smooth ride. I appreciated him giving the tour with a microphone so we all could hear.
Review provided by Viator
Anna_l
Sep 1, 2024
Great way to see all the highlights! - Derek does a fantastic job keeping you engaged with the history of the town and sharing funny stories. This is a great way to see all the highlights of Portland!
Review provided by Viator
83jond
Aug 28, 2024
Really outstanding tour of Portland - We have been on this tour 3 times as we take all our guests on it. Derek never fails to impress us with his knowledge of the city and environs. He is full of anecdotes about the people and buildings of Portland as well as lots of funny stuff and fun facts. Most enjoyable way to spend 2 hours.
Review provided by Tripadvisor
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up to 13 guests
1 Adult
September 2024
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