Tours/Portland/The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
Viator · group up to 13 pax

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

5.0(1,604)Portland1 hour
VIATOR5.0(634)TRIPADVISOR5.0(970)

Description

Welcome to my hometown! Hop aboard for an authentic 1 hour and 45 minute historical sightseeing tour of Portland, Maine and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, Maine. 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.

Tour Options

The Real Portland Tour

Itinerary

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We start at historic Commercial Street, the heart of Portland's working waterfront. See original cobblestone and brick that was laid in the 1850s.

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See one of the most beautiful granite buildings in all of Portland.

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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.

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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.

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We'll get a great view of the only remaining maritime signal tower in the U.S.

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Hear about the legends and lore regarding the oldest cemetery in Portland, first established in 1668.

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One of the busiest streets in all of Maine, we'll see Portland's eclectic downtown, Monument Square, and arts district.

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The neo-Gothic architecture of this cathedral built in 1869 dominates the skyline of Portland.

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This church is the oldest in Portland, and you'll learn about its rich history.

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See the home where Henry Wadsworth-Longfellow grew up and wrote his early poetry.

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We'll tour the center of downtown Portland, and its highly acclaimed Arts District.

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See one of the finest art museums in New England, and learn about its exhibits.

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See the statue of Henry Wadsworth Longfellow, born in Portland in 1807.

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Get an up close view of the Victoria Mansion, the finest example in the country of a 19th century Italianate brownstone.

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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.

20 min

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.

5 min

Get an up close view of Fort Preble (one of the oldest forts in Casco Bay) and learn about its storied history.

5 min

Get out for a photo of Spring Point Ledge Lighthouse, and its 900 foot long breakwater connecting it to the shore.

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Enjoy panoramic views of the Portland skyline from this beautiful park that sits directly across the bay from Portland.

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Get an up close view of the Liberty Ship Memorial, and learn about the thousands of shipbuilders who worked here during WWII.

5 min

Get a photo of Portland Breakwater Light (affectionately called "Bug Light" because of its small size).

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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.

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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.

Highlights

Knowledgeable, entertaining guide with 20 years experience giving tours of his hometown of Portland.
Air-conditioned vehicle

What's included

Included
Knowledgeable, entertaining guide with 20 years experience giving tours of his hometown of Portland.
Air-conditioned vehicle

Traveller Ratings

5.0
1,604 reviews
5
1,545
4
50
3
6
2
3
1
0

Important Information

  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • 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.
  • This is not a private tour. 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.

Reviews(1,604)

6
626madhug
July 22, 2026
The Real Portland tour

We had a wonderful time on the Real Portland tour. We drove through the major sights in town and had a longer visit to the lighthouses. Derek was humorous and informative and we would highly recommend this trip.

M
M920JBcolleeng
July 22, 2026
Good short tour

Our guide was very knowledgeable and personable. A native of Portland. I recommend going on this brief tour at the beginning of your visit to understand the city layout, see lighthouses and a verbal history. Saw a lot in a short amount of time.

J
juliehE5249UH
July 22, 2026
Great experience

We had a great experience with this tour! Derek was very knowledgeable and hilarious which made it a fun experience. He gave great restaurant suggestions. Would recommend to family and friends.

M
Mobile618726
July 22, 2026
Excellent Portland, MA tour guide

Derek was an excellent tour guide. Very knowledgeable and had tons of interesting facts about the city and the state’s history. Highly recommend!

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the local info, history, and fun facts! I take pride in giving an informative and entertaining tour of my hometown, and it’s nice to hear you enjoyed it so much. Thanks again, and hope to see you again in Portland, Maine!

M
Mary_A
July 21, 2026
Informative and Enjoyable Portland, Maine Tour

We took an excellent tour of Portland and the 3 lighthouses. Our guide was incredibly knowledgeable and funny. He shared fascinating history about the buildings and the city itself. We visited the 3 lighthouses, with plenty of time to take photos and enjoy the views. I highly recommend if you want and informative and enjoyable experience

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the local history, humor, and time spent at the lighthouses! I take pride in giving an informative and entertaining tour of my hometown, and it means a lot to hear you enjoyed it so much. Thanks again, and hope to see you again in Portland, Maine!

K
Karl_S
July 21, 2026
From Michigan

Great tour. Learned a lot and even loved the corny jokes. Would recommend to others based on our experience.

Operator response

I’m glad to hear you had a great time and learned a lot, and appreciated the humor too! I take pride in giving an informative and entertaining tour of my hometown, and it’s nice to hear you enjoyed it. Thanks again, and hope to see you again in Portland, Maine!

T
Tour53533063710
July 21, 2026
Summer 26

Derek was great! Very knowledgeable and funny!

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a great time! I take pride in giving an informative and entertaining tour of my hometown, and it’s nice to hear you enjoyed it. Thanks again, and hope to see you again in Portland, Maine!

M
MaryEllaC
July 21, 2026
Lighthouse tour

Derek was great! Funny. Lots of Dad jokes!! Very knowledgeable and proud if his city!!!

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the local info and humor! I take pride in giving an informative and entertaining tour of my hometown, and it’s nice to hear you enjoyed it so much. Thanks again, and hope to see you again in Portland, Maine!

L
Loren_W
July 20, 2026
Non stop information with...

Non stop information with lots of humor thrown in. One of the best tours we've ever been on. Excellent in every way.

Operator response

Thanks so much for the excellent review! It means a lot to hear my tour was one of the best you’ve ever been on! I take pride in giving an informative and entertaining tour of my hometown, and it’s nice to hear you enjoyed it so much. Thanks again, and hope to see you again in Portland, Maine!

C
cathiederochers
July 19, 2026
Great tour

Great tour. Extremely knowledgeable with a humorous flair. Thoroughly enjoyable.

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the local info and humor! I take pride in giving an informative and entertaining tour of my hometown, and it’s nice to hear you enjoyed it so much. Thanks again, and hope to see you again in Portland, Maine!

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