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(1,615)Portland1 hour
VIATOR5.0(639)TRIPADVISOR5.0(976)

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
1,615 reviews
5
1,556
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(1,615)

K
kellykD5308JF
August 2, 2026
Book the trip!

The tour was perfect from beginning to end! Derek clearly communicated all expectations, was prompt, professional, informative, educated, passionate about Portland (born & raised), witty, & hysterical. We loved his accent and storytelling, too. We had a blast laughing, learning, & exploring! Our group was so fun, too. We highly recommend booking this trip!

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a blast laughing and learning on the tour! 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!

R
Road48150
July 30, 2026
Worth it!!

Derek was a terrific guide. He was informative but yet clever and funny which kept our attention. I would totally recommend him!!!!

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!

P
P8406YOkarenr
July 29, 2026
Great experience

We had a fantastic time on this tour. Derek took us around Portland showing us the historic sights of the city. He was very knowledgeable and funny. He makes a connection with his passengers and answers all questions. Great tour.

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 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!

E
ec24ever2018
July 29, 2026
Professional and entertaining tour guy!

Wonderful trip experience. The tour guy is professional and entertaining.

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a wonderful experience! 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
michaeldB2253UJ
July 29, 2026
Great tour of Portland.

Very informative and entertaining. our guide Derek was outstanding!

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!

S
Samantha_M
July 29, 2026
Great tour. Even our teen gave it a 10 out of 10.

We really enjoyed our tour with Derek. He’s very knowledgeable and entertaining. This was our first time visiting Portland and he gave us a very thorough tour of the city and a lot of fun facts and history of the area. I 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 fun facts and history! 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!

J
Jhanve_N
July 29, 2026
Lighthouse fun

It was fun. We enjoyed ourselves. It was a little foggy at times but we still enjoyed ourselves. The tour guide was very informative.

Operator response

Thanks so much for your review! I’m glad to hear you had a fun 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!

T
Theresa_C
July 28, 2026
Beautiful Lighthouses

Derek was a great tour guide. He was very knowledgeable and funny. If you’re in Portland make sure you do this tour.

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, humor, and time spent at the lighthouses! 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!

T
TrailBlazer234757
July 26, 2026
Fantastic tour!

Derek was an excellent tour guide with an extensive knowledge of Portland and the surrounding areas. Would highly recommend.

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a fantastic time! 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!

J
John_G
July 26, 2026
A very informative and...

A very informative and enjoyable tour by a true Portland native and expert. We would highly recommend!

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!

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