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(1,624)Portland1 hour
VIATOR5.0(642)TRIPADVISOR5.0(982)

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
1,624 reviews
5
1,565
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(1,624)

A
agoodwin16
August 20, 2026
Great Tour

Derek was amazing! It was a great and informative!

P
Patricia_M
August 20, 2026
Family fun in the Real Pirtland

You have a real tour guide that is native born in Portland, Derek! He is a history buff, very funny, tells jokes, made our whole experience fun and memorable!

M
Michelle_B
August 19, 2026
Don't miss this tour...

What a fun and informative experience! Derek was hilarious and extremely knowledgeable about the city and light houses... was probably one of the best tours my husband and I have ever been on! We would 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 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!

S
ScottaG_H
August 15, 2026
Definitely a Must-Do!

This tour was Ah-mazing! Derek was very informative (he’s lived there all his life) and he had a great sense of humor! Derek also treated us to a “rap” about Portland he wrote himself. He has many accolades and we were fortunate that he shares what he knows with visitors to Portland.,

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 my Portland history spoken word rap! 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
MC77711
August 14, 2026
August trip!

Awesome exeperience. Wonderful Tour!

Operator response

Thanks so much for the excellent review! I’m glad to hear you had an awesome experience! 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!

B
BluePlanet-Family
August 14, 2026
Real history from a family man from Portland!!

Absolutely fantastic. Local with real family & history in Portland! I would do this tour again!

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a fantastic time on the tour! 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
Patricia_T
August 13, 2026
The Man With A Van

What a great tour! It was my first solo experience and first time in Maine. Derek showed us around his hometown, gave us insightful information, and provided ample time to take pictures. He was funny, kept us safe, and entertained. Thanks Derek!

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 photo stops! 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!

O
O5215VPsusanc
August 12, 2026
Great trip

Derek was awesome. Very knowledgeable and made the trip fun. Would definitely recommend this trip.

Operator response

Thanks so much for the excellent 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 so much. Thanks again, and hope to see you again in Portland, Maine!

2
231theresah
August 11, 2026
The Real Portland Tour a

If you are looking for a fun tour of Portland, pick the Real Portland Tour. Derek was fantastic. As a Portland native he knew so many interesting things about his city. You have 3 stops at lighthouses & the rest of the tour you are on the bus exploring the city. I wouldn’t hesitate to recommend this tour.

Operator response

Thanks so much for the excellent review! I’m glad to hear you had a fun time and appreciated all the interesting 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!

K
kristinsB7200UH
August 10, 2026
Portland & light house tour

If you have limited time to spend in Portland this tour is definitely a must do! Derek is great! Very informative and funny! We had a great time!

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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