The Real Portland Tour
City & 3 Lighthouses Historical Tour of Portland, ME with a REAL local, born & raised in Portland!
06/05/2026
In honor of National Donut Day today, here’s a picture of the monument in Rockport, ME dedicated to Captain Hanson Gregory who invented the hole in the donut in 1847
04/23/2026
Wreath laying ceremony this morning at Fort Williams Park in memory of the officers and crewmen of U.S.S. Eagle 56, which was torpedoed by German U-Boat (U-853) off the coast here on April 23, 1945. This ceremony takes place every April 23rd in the park.
04/14/2026
Another great day out here at Fort Williams Park!
04/04/2026
Beautiful day out here at Portland Head Light
03/24/2026
Before I start up tours for the season, I was able to plan one more epic journey down the Mother Road in honor of the 100th anniversary of Route 66 this year. Driving with the original trio of longtime best friends and Portland High grads that started the tradition back in 2005. It was our 8th trip on Route 66 and as always it was an adventure. From the Capital of Route 66 Tulsa, OK and a private tour of the Outsiders House Museum to ending in our favorite 66 town of Flagstaff, AZ, it was 4 states in 3 days, over 1100 miles logged. From the Center of the Universe in Tulsa, to the 100th Meridian Line in Erick, to the Midpoint of Route 66 in Adrian, to the Continental Divide, to starting a day standing on the corner of Route 66 and Route 66 in Albuquerque and finishing the day standing on the corner in Winslow, AZ, from a jump in the waters of the Blue Hole in Santa Rosa to a stop in the original Las Vegas in New Mexico and a night in Santa Fe, and from the 66 Junkyard Brewery in Grants to an off-road adventure finding an original unpaved section of Route 66 in the middle of the Painted Desert. We drive each trip in the memory of our dear friend Filip from Stockholm, Sweden. He was able to drive the entire route with us back in 2008. On that trip, we had the pleasure of meeting Fran Houser, the former owner of the Midpoint Cafe. Fran was the inspiration for the Flo car in the movie Cars. We were very sorry to hear that she passed away last summer. Back in 2008, she let me write the last line of a poem I had written about Route 66 across the front bumper of her truck. Fast forward 18 years later, and with the help of some amazing folks on the road, we were able to find the truck, and all these years later, the line I wrote was still there.
Back in March 2020 just before the world shut down, I surprised Jeff and Ben with a stone in Filip’s honor on the corner of Winslow, AZ with a shortened version of the same line from the poem. We said from that day forward, each trip we made we would stop at “Filip’s stone.” We love this route and the people on it, and all the friends and family that have joined us on these crazy trips over the years. Happy 100th Route 66!
03/11/2026
Had another awesome stay at the Marriott Vacation Club at Custom House, Boston. We stay at the Custom House every year and it’s always a great time. The inside of the building is beautiful with displays about its history, and as a guest you get free access to the top, the 26th floor just above the clock tower. It was Boston’s first skyscraper. The Custom House was built between 1837 to 1847, and the tower was built between 1913 to 1915. The 360 degree views from the top are amazing.
I also took my backup tour guide to the Massachusetts State House to see another hidden piece of history connected to my very great grandfather, Captain Isaac Davis, who was the first officer killed in the Revolutionary War. If you go to Doric Hall inside the state house, just beside the portrait of Abraham Lincoln, you will find two cannons which have inscribed the following: “The Legislature of Massachusetts, consecrate the names of Major John Buttrick and Capt. Isaac Davis, whose valour and example excited their fellow-citizens to a successful resistance of a superior number of British troops at Concord Bridge, the 19th of April, 1775, which was the beginning of a contest in arms that ended in American independence.”
03/04/2026
Did a quick trip to Florida last week and got a chance to tour the inside of Saint Augustine Lighthouse and climb to the top. Last year I started the year by touring Key West Lighthouse, then did a trip to Portland, England to tour Portland Bill Lighthouse, and finished the year finally getting a chance to tour the inside of Portland Head Light.
Saint Augustine Lighthouse has been the tallest I’ve climbed so far - 219 steps to the top. The views were great!
10/27/2025
After over 20 years giving tours, I was finally able to tour the inside of Portland Head Light tonight, and walk to the top. Got some great pictures at sunset. I started this year in January touring the Key West Lighthouse, then toured the Portland Bill Lighthouse in Portland, England on July 4th, and now finally getting a chance to tour the inside of Portland Head Light this evening brought it all full circle. Big thanks to Tony, one of the park rangers at Fort Williams Park, for taking the time to give me a tour of the inside of the lighthouse. Tony and my dad were teammates on the legendary fast pitch softball team Olympia Sports in the ‘80s in Portland. It was an honor to be able to tour the inside of the lighthouse with him. Here are some photos from tonight, and I also added a photo from Key West Lighthouse and Portland Bill Lighthouse at the end
09/20/2025
Took my backup tour guide this morning to the reenactment of Captain Henry Mowatt bombing Portland (then known as Falmouth) on October 18th, 1775. She’s got my red hot dog joke down pat, but if she’s gonna take over the reigns of The Real Portland Tour someday she’ll need historical knowledge too
07/07/2025
I finally visited the original Portland that my hometown of Portland, Maine is named after - Portland, England! It was the ultimate research trip for my tour. The trip also included a stop for a few pints in Dublin, a Stevie Wonder concert at the Lytham Festival in Lytham, England, a stay at the Hard Days Night Hotel in Liverpool with a Beatles tour, and an Oasis concert at Principality Stadium in Cardiff, Wales. It was 3 countries in 4 days with my longtime best friend, Jeff Morris. We’ve been friends since we were 5 years old growing up in Portland, and being able to fit all this in in 4 days was epic. We arrived in Portland, England on July 4th, which was 239 years to the day that Portland, Maine was incorporated as a city and named after Portland, England (we were incorporated as a city with the name of Portland on July 4, 1786). The similarities of the two Portland’s are pretty amazing - Portland, England has 3 lighthouses, we got a tour of the inside of the main lighthouse on their rocky coast (called Portland Bill Lighthouse) and walked the 153 steps to the top. Next to the lighthouse is a restaurant called the Lobster Pot (yet they have no lobster on the menu). We ate fish and chips at the Lobster Pot, hiked the southwest coast path on their rocky coast, and hit up the local Portland pub, called The George Inn. We walked in the pub and Shipyard Pale Ale from Portland, Maine was on draft (a coincidence I still cannot believe). There is a group of locals that hang out at the bar on Friday evenings. They invited me and Jeff to their table, bought us some pints, and we shared stories of both Portlands. They had no idea of all the similarities, it was a wonderful night of many stories and laughs. I grabbed my guitar, Jeff sang, and we did a song list of Beatles and Oasis, singing along into the night at the pub with our new friends from the original Portland. The greatest tour research trip I could have ever asked for - Jeff and I have referred to this trip as The Songs in the Key of Our Lives…
Click here to claim your Sponsored Listing.
Category
Contact the business
Website
Address
96 Commercial Street
Portland, ME
04101
Opening Hours
| Monday | 8am - 6pm |
| Tuesday | 8am - 6pm |
| Wednesday | 8am - 6pm |
| Thursday | 8am - 6pm |
| Friday | 8am - 6pm |
| Saturday | 8am - 6pm |
| Sunday | 8am - 6pm |