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

1 hour 45 minutes
Free cancellation
1 - 13
Mobile ticket


Welcome to my hometown! Hop aboard for an authentic 90 minute sightseeing tour of Portland and 3 lighthouses with an experienced guide who is a real local, born and raised in Portland, ME.

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.


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

What to expect

This is a typical itinerary for this product

Pass By: Commercial Street, Portland, ME

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

Pass By: United States Custom House, 312 Fore St, Portland, ME 04101-4110

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

Pass By: Fort Allen Park, Maine

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.

Pass By: Eastern Promenade Trail, Portland, ME 04101

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.

Pass By: Portland Observatory, 138 Congress St, Portland, ME 04101-3608

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

Pass By: Eastern Cemetery, 224 Congress St Mountfort St., Portland, ME 04101-3639

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

Pass By: Congress Street, Portland, ME

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

Pass By: The Cathedral Of The Immaculate Conception, 307 Congress St, Portland, ME 04101-3638

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

Pass By: The First Parish Portland Unitarian Universalist, 425 Congress St, Portland, ME 04101-3505

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

Pass By: The Wadsworth-Longfellow House, 489 Congress St, Portland, ME 04101-3414

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

Pass By: Arts District, Congress Street, Portland, ME

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

Pass By: Portland Museum of Art, 7 Congress Sq, Portland, ME 04101-3802

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

Pass By: One Longfellow Square, 181 State St, Portland, ME 04101-3701

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

Pass By: Victoria Mansion, 109 Danforth St, Portland, ME 04101-4504

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

Pass By: Fort Williams Park, 1000 Shore Rd, Cape Elizabeth, ME 04107-1916

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.

Stop At: Portland Head Light, 1000 Shore Rd, Cape Elizabeth, ME 04107-1916

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.

Duration: 20 minutes

Stop At: Fort Preble, South Portland, ME

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

Duration: 5 minutes

Stop At: Spring Point Ledge Lighthouse, 2 Fort Rd Southern Maine Community College Campus, South Portland, ME 04106-1611

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

Duration: 5 minutes

Pass By: Bug Light Park, South Portland Greenbelt Pathway, South Portland, ME 04106

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

Pass By: Liberty Ship Memorial, Bug Light Park 0 Madison St, South Portland, ME 04106

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

Stop At: Portland Breakwater Lighthouse, Bug Light Park End of Madison Avenue, South Portland, ME 04106

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

Duration: 5 minutes

Pass By: John Ford Statue, Gorhams Corner, Portland, ME 04101

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.

Pass By: Old Port, Commercial St, Portland, ME 04101

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.

Additional information

  • 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.
  • 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.
  • Unfortunately no pets/animals of any kind can be accommodated on board. The tour does not pickup/drop off at the cruise ship terminal, and it does not pickup/drop off at hotels. Wheelchairs, walkers and luggage do not fit in the van. You'll be riding with 13 people in the high-roof Ford Transit van.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This tour/activity will have a maximum of 13 travelers
  • Confirmation will be received at time of booking

Ticket delivery

You can present either a paper or an electronic voucher for this activity.


For a full refund, cancel at least 24 hours in advance of the start time of the experience.
May 2022

Derek awesome job. Lot of information. Friendly & knowledgeable Meet people from other states. Thank you

March 2022

True local with fun facts and great historical commentary. Perfect way to see the main sights Maine has to offer.

May 2022

Derick was great! Very informative and entertaining. He answered all of our questions and knew his history!

April 2022

Derek was excellent! He was funny, informative and being a true native of the area he shared stories and pointed out the little things that made it fun and interesting. It was a real pleasure being on his tour. We highly recommend it!

April 2022

This was a great way to see the city and visit 3 lighthouses. It's a small group so it's very personal and Derek is great. He added some humor to the tour so that was a lot of fun too :)

April 2022

Super great tour guide with historical knowledge & personal history of the town of Portland that'll give you some really nice highlights of the city. Wonderful way to squeeze in all the lighthouses in a day trip! Went to Holy Donut afterwards and explored Congress Street.

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