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

Recommended by 99% of travelers

Badge of Excellence

Portland, USA

Trending

Booked 5+ times in 12 hours.

1 hour 45 minutes (approx.)
Mobile ticket
Offered in: English

Why travelers loved this

5.0

· Jenny_G ·

Jun 2026

Delightful and informative tour guide/owner, Derek. I learned so much in 2 hours about Portland ME. Definitely a value for the experience. The group size was perfect, van was clean, and Dad jokes hilarious. We had just the right amount of time to visit each lighthouse. I would recommend this tour!

· Robin_R ·

Jun 2026

You should ONLY book with this guide! Great communication, easy meet up spot, very knowledgeable and great recommendations! If you want a ton of information to start your week in Portland or only have a short bit of time in town this is your guy!!!!

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Overview

Explore the heart of Portland and head out to see some of the area's hidden gems and less-visited spots with this guided sightseeing tour. Your guide, a born-and-raised Portlander who works as a college librarian by day, shows you off-the-beaten-path locations and shares with you all sorts of local lore along the way.

Get off-the-beaten-path on a guided tour of the real Portland, Maine
A historian and librarian guide leads the way
Travel in the comfort of an air-conditioned vehicle
Visit three picturesque lighthouses

What's Included

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

Meeting and Pickup

Meeting point

96 Commercial St, Portland, ME 04101, USA
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.

End point

This activity ends back at the meeting point.

Itinerary

Make your own way to a central location in Portland 15 minutes before your chosen departure time to begin your bust tour of the city. Led by a true local, this sightseeing tour covers Portland and its three lighthouses.

Starting on historic Commercial Street, see Portland's landmarks and hidden gems, such as the United States Custom House, Fort Allen Park, and the Eastern Promenade Trail, adorned with Victorian-era homes and the iconic Portland Observatory.

Explore the Eastern Cemetery's legends and the vibrant downtown on Congress Street and venture to Fort Williams Park to marvel at Portland Head Light, the most photographed lighthouse in the country, alongside Fort Preble and Spring Point Ledge Lighthouse.

Capture Bug Light Park's panoramic views and discover the Liberty Ship Memorial before glimpsing Portland Breakwater Light.

The tour concludes with a ride through Old Port, the bustling downtown and waterfront district.

Commercial Street (Pass By)

United States Custom House (Pass By)

Fort Allen Park (Pass By)

Eastern Promenade Trail (Pass By)

Portland Observatory (Pass By)

Eastern Cemetery (Pass By)

Congress Street (Pass By)

The Cathedral Of The Immaculate Conception (Pass By)

The First Parish Portland Unitarian Universalist (Pass By)

The Wadsworth-Longfellow House (Pass By)

Arts District (Pass By)

Portland Museum of Art (Pass By)

One Longfellow Square (Pass By)

Victoria Mansion (Pass By)

Fort Williams Park (Pass By)

Portland Head Light

20 minutes • Admission Ticket Free

Fort Preble

5 minutes • Admission Ticket Free

Spring Point Ledge Lighthouse

5 minutes • Admission Ticket Free

Bug Light Park (Pass By)

Liberty Ship Memorial (Pass By)

Portland Breakwater Lighthouse

5 minutes • Admission Ticket Free

John Ford Statue (Pass By)

Old Port (Pass By)

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Near public transportation
Most travelers can participate
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.
This tour/activity will have a maximum of 13 travelers

Supplied by

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Reviews

5.0

based on 1,645 reviews

Total reviews and rating from Viator & Tripadvisor

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Sort by: Most insightful

Great tour in Portland, Maine

Wayne_W, Sep 2026

We enjoyed our Portland tour with Mr Davis. He was so informative and entertaining! We like the smaller group, compared to the large NCL excursions and Viator is definitely the better deal.

Response from Host, Sep 2026

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

Awesome! 10 stars

Wendy_W, Sep 2026

Best tour ever! I will recommend this to all my friends and family. Couldn't ask for more from Derek.

Response from Host, Sep 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time and would recommend my 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!

Great guide, born and...

Kenneth_H, Aug 2026

Great guide, born and raised in Portland. Great knowledge and super friendly. You will thoroughly enjoy this tour.

Response from Host, Aug 2026

Great Adventure

James_M, Aug 2026

We had a great time. Derek had a ton of stories about the city of Portland. Very interesting and the lighthouses were wonderful. Derek’s jokes and humor had us all laughing

Response from Host, Aug 2026

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

We really enjoyed our...

leigh_a, Aug 2026

We really enjoyed our tour. Derek is a great host. Very knowledgeable about the Portland area; friendly, funny. The van was clean.

Response from Host, Aug 2026

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 cleanliness of my tour van! 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!

Enjoyed

Jo_C, Aug 2026

Great guide. Very enjoyable and informative. Loved all the lighthouses. Guide told Dad jokes and was very likable.

Response from Host, Aug 2026

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!

A must do in Portland

Carlos_R, Aug 2026

Derek was fantastic!!! So knowledgeable and born and raised in Portland. He had us laughing the entire time and was very respectful and kind to the elders who were there.

Response from Host, Aug 2026

Portland, the Inside Story.

Cynthia_B, Aug 2026

Derek is a wonderful guide, full of Portland info only a native would know. His comedy act isn’t quite ready to take on the road but his tour is full of fun and interesting facts as well as good humor! We highly recommend!

Response from Host, Aug 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the fun facts, local info, and humor! I agree I’m not quite on a roll enough yet with the hot dog puns to mustard up enough to hit the road! 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!

Lighthouses and More

Gretchen_J, Aug 2026

Very informative and great way to see the highlights and lighthouses of Portland and know where you would like to revisit along the route during your stay.

Response from Host, Aug 2026

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

Family fun in the Real Pirtland

Patricia_M, Aug 2026

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!

Response from Host, Aug 2026

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

Don't miss this tour...

Michelle_B, Aug 2026

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...

Response from Host, Aug 2026

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!

Definitely a Must-Do!

ScottaG_H, Aug 2026

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.,

Response from Host, Aug 2026

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!

The Man With A Van

Patricia_T, Aug 2026

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!

Response from Host, Aug 2026

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!

Great tour. Even our teen gave it a 10 out of 10.

Samantha_M, Jul 2026

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.

Response from Host, Jul 2026

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!

Lighthouse fun

Jhanve_N, Jul 2026

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

Response from Host, Jul 2026

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!

Beautiful Lighthouses

Theresa_C, Jul 2026

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

Response from Host, Jul 2026

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!

A very informative and...

John_G, Jul 2026

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

Response from Host, Jul 2026

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!

“Derrick the Van”!

Rosemarie_N, Jul 2026

Derrick “the van man” was wonderful! We loved all of the Portland history and the lighthouses were stunning!! There is nothing better than having a tour of a city by a local who is so knowledgeable & funny! ❤️

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the history, humor, and 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!

Informative and Enjoyable Portland, Maine Tour

Mary_A, Jul 2026

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

Response from Host, Jul 2026

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!

From Michigan

Karl_S, Jul 2026

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

Response from Host, Jul 2026

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!

Non stop information with...

Loren_W, Jul 2026

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

Response from Host, Jul 2026

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!

Loved The Real Portland City Tour!

Tiffany_G, Jul 2026

Derek was PHENOMENAL! He is a local with so much knowledge about Portland’s history. On this tour, you’ll see the city and explore a couple of lighthouses all while learning about the city. Other highlights included the intimate tour (only 15ish spots) versus larger, more impersonal tours, and recommendations from Derek regarding local spots to be sure not to miss!

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the local info, history, recommendations, and the smaller, more personable 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!

Derrick is the Real Portland Deal

Kathleen_J, Jul 2026

Derrick was amazing! His love of his hometown and his knowledge were amazing. He was personable and share tidbits only a local could provide. The transportation was clean and comfortable. He was timely and provided extra information for those of us interested in reading or watching to get more details! You will not be disappointed!

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the local info, recommendations, and cleanliness and comfort of my tour van! 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!

Great way to spend a morning or afternoon

Celeste_C, Jul 2026

Derek made sure everyone had a great time and shared a lot of information throughout the tour. The lighthouse stops were perfect with plenty of time to get great pictures. The van was very neat and well air conditioned. Highly recommend this tour.

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the local info, lighthouse stops, and the cleanliness of my tour van! 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!

Don’t miss this tour!

Annette_L, Jul 2026

Excellent tour with lots of fun facts by a local, knowledgeable and entertaining guy! Glad we did this tour!

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the fun facts and local info! 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!

Portland with a Pro!

Cynthia_K, Jul 2026

Such a fun time! Derek was amazing. So knowledgable about the area & history. Great guide, great sense of humor too! We were fortunate to have selected the best tour guide! Seriously recommend doing Portland with the pro!

Response from Host, Jul 2026

Thanks so much for the excellent review! I glad to hear you had a fun time, and appreciated all the local history and humor! 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!

Well worth it!!!

James_S, Jul 2026

Very informative, interesting, funny. He really knows the area and the “lore”. He really paints a picture and gives a lot of content with each stop.

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time, and appreciated all the local lore 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!

Derek’s Real Tour

Rosalieand_M, Jul 2026

This was a fabulous tour with Derek. He is not only knowledgeable but hilarious. He knows the city well being a local there. This was truly an enjoyable trip. I highly recommend this tour.

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you had a fabulous time on the tour, 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!

Derek was very funny and...

Arlynn_P, Jul 2026

Derek was very funny and charismatic. Learned a lot and he gave great recommendations for places to eat.

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you learned a lot, and appreciated all the humor and recommendations! 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!

Portland City & Lighthouse tour

Daniel_T, Jul 2026

A great way to see the top sites. Derek the guide was great. He is a native and knows the city well. He was also entertaining. We highly recommend this tour!

Response from Host, Jul 2026

Thanks so much for the excellent review! I’m glad to hear you had a great time and would highly recommend my 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!