I found this tour through TripAdvisor and it deservedly gets 5 stars on that site too. Linda is a…read morewealth of information about Portland Maine. In fact, her detailed history helped jumpstart our knowledge of the region and the subsequent ports we would visit that share a similar history. We were fortunate that the day we went, we were the only ones signed up so basically had a private tour for the morning. We all enjoyed the morning so much we didn't even realize she had gone 45 minutes over the allotted walking tour time. The price is extremely reasonable for the amount of past and present information she provides. She also provides a military discount which makes it an even better deal.

I highly recommend taking this tour. Lind, our guide, was extremely knowledgeable and gave us a 3…read morehour tour. It was a very hot day and it must have scared away other tourists but she did not skimp on this tour even though there were only 2 of us. It was worth a lot more than we paid. I feel like I deserve college credit for all the knowledge she imparted on us.

This was a super interesting Locally owned tour of Portland . We visited some beautiful historic…read morelight houses and toured the downtown areas. The driver (and owner) had lots of local interesting information to share and he was enthusiastic and really made the tour fun for our group. Actually was one of the best local tours I have ever been on. Highly recommended when visiting Portland for the first time.

loved this tour! great commentary and good jokes! Very interesting and well done. I would…read moredefinitely recommend this trip!

Dugan is an expert tour guide and passionate about history! He provided a superb and detailed…read morehistory of African Americans in Portland, ME from the colonial era to the current day. We loved the amazing story of Susan Rice and her mother (Lois Rice) who each had a tremendous impact on education and public policy. Our family enjoyed learning about the many changes in downtown Portland from the 1700s to the 1950s and hearing the stories of remarkable leaders in the community over generations. We appreciated the enthusiasm and concern of Dugan to make sure the entire group was OK during the walk on a hot summer day (the shaded "rest breaks" were a plus). Also, he was open to questions and made everyone feel welcome. Overall, I would strongly recommend any of the walking tours! You are bound to discover something new.

Dugan was a very cheerful and knowledgeable tour guide. He began his walking tour promptly. Hubs…read moreand I enjoyed hearing about all the nuggets of history in Portland. I heartily recommend his tour for a pleasant two hours of familiarizing oneself with the Old Port surroundings.

My mum and I absolutely love red cloak tours!! The stories are very interesting and spooky. The…read moretour guide is really kind, and happily answers any questions. I went to the bath and wisscasset tours and found out so much about houses and places I may have overlooked if not for this new knowledge. Call me crazy, but I think I may have saw a ghost in the top window of a house in wisscasset, when nobody was home.

My family and I took this tour the other night. There were 12 people on the tour. Our guide…read morecombined stories about the history of the city as well as a number of different ghost stories. She was articulate and told some very good stories both as to the city and its origins and the different buildings that are haunted. At the end of the tour I kept looking in Opera House hoping to see the ghost that apparently still hangs out there. We all enjoyed the tour and would highly recommend it if you are visiting the town.

I attended the Portland: Old Port Culinary Walking Tour on Sunday, June 14, 2026 at 10:30 am with…read moreAnne and Ross. Usually, there is only one tour guide and it was supposed to be Anne only but Ross joined in as well. The Old Port Culinary Walking Tour is a foodie tour with a mix of history and culture. Our group consisted of 13 people. The tour starts at Andy's Old Port Pub with an introduction from our tour guides. At Andy's Old Port Pub, we were seated in the backroom and had a seasoned, grilled fresh haddock with house-made pickled vegetables, pico de gallo and lime crema in a corn tortilla and Andy's house Lager. Ross talked about the suspicious happenings and history at Andy's Old Port Pub. They both talked about Harbor Fish Market which was right across the street and how the seafood never see the back of a truck. I thought the fish taco was okay and was probably my least favorite food item from the whole tour. Andy's house Lager was very smooth and I really enjoyed it. Then, we walked next door to Gilberts Chowder House where we had a choice of Clam Chowder, Haddock Chowder, Corn & Chicken Chowder, Seafood Chowder, or Seafood Chili. I chose the Clam Chowder. The Clam Chowder was thick and not as creamy as I usually like my clam chowders. Here, Anne was showing us pictures of lobster abnormalities. After having our chowder, we walked to the historic U.S. Custom House and old fishing docks. We even got a postcard of the old fishing docks which was a nice souvenir. Next, we stopped at Rigby Yard and were seated in a small private room. We were offered several drink options; I chose a glass of prosecco. We had the Fresh Maine Lobster Roll with fresh Maine lobster meat Maine-style, tossed lightly in mayo, lemon, and sea salt served on a brioche roll with chips. The lobster was definitely fresh and good. The last two stops were dessert spots: Dean's Sweets and The Gelato Fiasco. We had a needham which is a confectionery dessert bar made from sugar, chocolate, coconut, and potato and we had the option to choose another truffle. I chose a blueberry one. At The Gelato Fiasco, we were able to choose 2 different flavors. Funny enough, I had went to The Gelato Fiasco the night before and it really is delicious gelato. I was glad to try different flavors. The tour finished about 1:45pm. The tour guides thanked us for spending our time together. The Portland: Old Port Culinary Walking Tour was fun and I enjoyed meeting the other people in our group. Anne and Ross were very knowledgeable with Portland's history and food scene. They had good recommendations for other things to do in Portland. The food we had on the tour was okay according to my opinion, but it was definitely a good variety of Maine dishes.

We came to Maine very VERY early season (March 20th-24th) and were looking for something to do…read more Most of the area is still in full 'pre season' mode, with many restaurants and services closed, especially during the week. We found the walking Food tour on Viator and jumped at it - and boy were we glad that we did! Because of the time of year, my wife and I were alone on the tour and as such got to spend around 3 hours with our guide, Ray Sapirstein. Putting aside Ray's obvious love for Portland and food in general, he was a charming guy - keeping us engaged and entertained with stories about the area for the entire duration of the tour. Ray is a PHD trained historian and, as such, was able to fill in a lot of color about the area, going beyond the 'food' aspects of the tour, describing the 'hilly roads' which were sand dunes were covered up to build out the city. Add to that the fact that he took us to several places that we NEVER would have found via googling for 'best ofs' and would have been a HUGE failure to miss! Andy's Old Port Pub - a neighborhood bar (don't call it a dive, though in my mind it qualifies). Spend some time chatting with Thomas, the owner, and Steve the bartender - and had what I can only describe as the single best haddock taco I've ever had in my life. Do not judge a book by it's cover: this place is AWESOME. Great craft beer tap list, and a warm and friendly environment. If I lived in the area, this would be my regular. From there we went to Gilbert's Chowder house right next door - Ray was again right: don't sleep on the seafood chili - it was RIDICULOUSLY amazing. After that we paid a visit to the Harbor Fish Market where we got to see the recent catches, and as Ray pointed out the 'transparency' of the thing: fish are cleaned and prepped for sale right where the customer can watch, and all fish are labeled as 'fresh' (with VERY few pre-frozen exceptions). This is also the place to go if you want to buy Maine swag. From there we proceeded to Rigby House, an unassuming 'coffee shop and workspace' that Ray promised us had nothing short of the best lobster roll in Maine: I've had some good lobster rolls so I can't quite commit to that, but the bread it was built on was FANTASTIC, baked locally from one of the bakeries rated tops in the nation right in Portland. This stop came with either 2 samplers or 1 full pour from their 20+ menu. Don't miss the blueberry ale. It's a rare treat and again, came from Ray's love of his city. From there, we visited Dean's Sweet shop for a couple of truffles and terrible jokes, and then Fiasco's Gelato to round up our day - try the lobster gelato, it's weird and not something I'd necessarily do again...but glad to have had the experience. The whoopie pie gelato was top notch and the blueberry was one of the best gelatos I've ever had. For a 3 hour tour, with all food included, we were certainly full and happy. The walk was short - I don't think we wandered more than a mile in total - and when we were showing signs of being "Help me I'm not from Maine cold", Ray took us into Grittys, another neighborhood bar just for a warm up.

The Skolfield-Whittier House was constructed between 1858-1862 and has remained virtually unchanged…read morefor more than 100 years. It is an amazing building that allows you to step back in time guided by a fantastic staff and group of docents. Highly recommend.

Loved how the how was left like it was when the family turned it over. Everything is original…read more Our guide was great and very knowledgeable

Khaled and Al were fantastic! We had a large group traveling from all over the US, and I was in…read morecharge of planning our excursion. Khaled was wonderful to work with and put me at ease to make sure our group would have a great experience. Al was a friendly and informative guide. Highly recommend!

Absolutely loved this tour and our tour guide Shawn K. He…read morewas so knowledgeable and easy going. He gave us a taste of the local history, culture, industry and suggestions for further explorations after getting off his tour. Enjoyed hearing the impact Irish immigrants had on the area. Something you don't hear much about anymore. It was evident Shawn knew the area and cared about those on the tour not just reading a script. Will ride with Shawn again cuz I know his next tour will provide new and exciting tales of Portland Maine.

We had a great time on this walking tour. Our guide Dugan brought Portland to life with interesting…read morefacts and stories. All questions were welcomed and answered. The tour starts on time, so don't be tardy to this highly recommended excellent tour.

Our group of five had a great tour with Pete on a crisp sunny day. Learned history and saw sites…read morefrom Monument Square to the waterfront area; the Eastern Prom, Portland Observatory and more. The guide was very knowledgeable and his sense of humor meshed well with our crew. It was pleasant 3+ mile walk that capitalized on some terrific views. The exercise helped whet our appetite for lunch at one of many restaurants Pete recommended.