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    Maine Day Ventures

    4.5 (257 reviews)
    Closed 9:00 am - 5:00 pm

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    Kelly D.

    Awesome tour! Lots of history. Good food portion sizes. Timothy is a great storyteller and a charismatic guide. I appreciate that he is a Maine native, too, as he had lots of history, knowledge, and first-hand experience with the area.

    Andy's Old Port - Allagash White Beer and Haddock fish taco
    Katie N.

    Maine Day Ventures was such a great way to experience food in Portland. We had so many stops and tried so many places. The food is also not small samples, it is full sized items!!! We tried the local beer, fish tacos, chowder, lobster rolls, chocolate, and gelato! We also were able to learn about the history of Portland, which was a nice added perk. Even though we did the walking food tour, it isn't a lot of walking so don't be discouraged to take the tour. It is totally worth it and a great way to learn about Portland and its food scene. Kim was our guide me and she was highly knowledgeable and made it fun to walk around eating for the afternoon. Places we went: Andy's Old Port Gilbert's Chowder House Harbor Fish Market Rigby Yard Wharf Street Dean's Sweets Gelato Fiasco

    Fish taco
    Marg G.

    We toured with Ross yesterday for the Seafood Lovers walking tour and his history knowledge really added to the experience! The food was really good - fish taco at Andy's, chowder at Gilbert's, samples from the fish market & Dean's Sweets, a full lobster roll from Rigby Yard, and gelato - we were stuffed but happy with how much we learned about the area, the culinary scene, and the history of Portland. Well worth time and money!

    Clam Chowder
    Amy D.

    We spent three days in Portland and chose to do this wonderful food tour on the first day so we could get the lay of the land. It was the perfect way to learn about the food and history of the area. Our guide Timothy also gave numerous suggestions about places to eat and things to do during our visit. We had a great fish taco and a beer, then a choice of clam chowders, an entire lobster roll and chips, two pieces of custom chocolates, and a huge cookie! I highly recommend this informative and yummy tour.

    Belgian paver stones off commercial street
    Lakshmi R.

    My fiancé and I came to Portland for a week long getaway. As it was our first tjme, we wanted to hit some of the more touristy attractions and booked the Architecture & Walking Tour through Maine Day Ventures and had a great experience! For first timers, this is a great way to get a lay of the popular parts of town along the waterway and through the city center. Our tour guide Tyler was incredibly engaging, knowledgeable and inclusive and made the experience fun! It was a warmer morning so Tyler was also conscious to find shade for the group whenever possible. I would highly recommend booking a tour with Tyler if you're interested in learning about the history of Portland and seeing varying architecture styles.

    View of the port from the Olive store

    Food tour with Bill through Rockland was the best. We did it as a family and enjoyed the food and history mixed in during the tour. Bill was a great pilot for the adventure.

    Andy's Haddock taco

    This was a fantastic tour! Our guide, Kim, was super knowledgeable and we learned so much about the state of Maine and city of Portland. She also gave us great recommendations for places to try and things to do. The food was all fantastic too. We went to Andy's Old Port Pub, Gilbert's Chowder House, Rigby Yard, Dean's Sweets, and Gelato Fiasco. We had good sized portions! I'd highly recommend this to a Portland visitor!

    Bench seating and two individual chairs available.
    Shannan S.

    Excellent experience and would absolutely recommend to anyone to enjoy! The small group size, boat quality -- and most of all the cheer & hospitality of the crew (Brenden & Moriah) we're top notch! The oysters were excellent and there were plenty to go around our group. The captain let my mom drive the boat and even though she didn't like oysters all that much, this was a great low pressure way to try them out!

    Robin M.

    First and foremost, this tour was great in overall experience. Close to a 3.5. However, upon its resolution there were a few things my husband and I wished were slightly different. First, let's cover the good stuff--Highlights: Our guide, Ray, was very knowledgeable about many things historically and culturally relevant to the Portland area, which was delightfully interesting and he answered questions very openly. The food was delicious! We definitely tried a few places worth revisiting on future return trips to Portland, which was a great experience. (Most notable were Gilbert's Chowder House, Standard Baking Co., and Rigby Yard!) The small setting was kind of nice for us as newcomers-- it was just myself, my husband, and Ray on this tour. We enjoyed his conversational approach to the tour and liked the fun, non-food parts of the tour showcasing how close the Harbor Fish Market is to many of the main restaurants on or near Commercial St. Now, the not-so-fun part--Lowlights: All but 1 restaurant were either on or adjacent to Commercial St, so it is incredibly likely we would have found many (if not all) of the locations we visited on the tour without the almost $300 price tag for two people. (We had already visited 1 of the places the day before just because it was on Commercial St and seemed like a great place to try). {it was! Try out Standard Baking Co if you get a chance - I highly recommend the morning bun!!} The food was good, but honestly, pricing the items out for the two of us would have certainly cost less than the tour itself. Save yourself the money on the tour and just walk into most of the restaurants on Commercial St to sample the same foods on the tour experience. The final, and in my opinion, most disappointing aspect was the way Ray closed our tour by basically saying "great; thanks for coming on the tour, you can tip me on Venmo now". - I had no problem tipping Ray; actually, I was looking forward to doing so. - However, it was the suddenness and almost anticipative way he expected the tip which caught us off guard. "It's customary to tip me once we're done here" - not exactly words you want to hear at the end of an otherwise humble little tour. - I did not have enough cash to offer him a physical tip, and we did not have Venmo set up (if we had been told this was needed for gratuity BEFORE, it would have been a far less clumsy and uncomfortable interaction at the end of the tour) - As a result, I had to tell Ray that we would have to tip him a little later once we could get to the car and set up Venmo and his response was sort of pressuring, saying that he tips out the businesses himself. -- As if I don't know that? Not to mention, I have no way of knowing how much he is tipping them / comparing to our own level of tipping. He seemed skeptical and untrusting that I would tip, which honestly made me not want to tip him as much as we had planned. - Asking for a gratuity is already an awkward conversation, but his pressuring attitude (which shifted somewhat rapidly from the friendly tour-guide vibe from moments before the tour ended) left us with a bad taste in our mouths at the end of the day. TLDR: Did we have fun? Yes. Was the food good? Yes. Would we do this again? Probably not. If you do this tour - bring cash for a tip or have Venmo set up before you go!

    Lobster cages ready to go

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    Page 1 of 7

    Ask the Community - Maine Day Ventures

    Review Highlights - Maine Day Ventures

    His dinner recommendation to dine at Evo was spot on and like Timothy, we also fell in love with the carrots.

    Mentioned in 20 reviews

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    United States Custom House

    United States Custom House

    5.0
    (1 review)
    0.8 km

    One time at the US Custom House I drank pickle juice in what was Joshua Chamberlain's old office…read morewith two of my best friends. The only thing that was missing with Angus King. To be honest, if he had been there I probably would have died of sheer happiness. It would have been horrible to pass away so young, but with that much epic Maine-ness happening all at once, it would have come as no surprise to my friends and family. The United States Custom House here in Portland was built with fire proof granite from New Hampshire between 1868 and 1872. When you first enter, there is a grandiose hall with a checkerboard floor, walnut counters on either side of the room, and an iron-railed balcony encircling the room. From what I know, at the heart of its purpose, it was where merchants used to come to pay their tariffs on imports/exports. Now, here are things I'll probably get in trouble for telling you: 1. This place might actually be a front for Gringotts Wizarding Bank 2. I may or may not have accidentally been locked in the basement after the alarm was tripped and the police showed up (it's much more fun to not know the context of which this story comes from, so I'll leave it at that) 3. I was told there used to be a moat and a dungeon here. I'm not THAT gullible, but... a girl needs something to believe in, y'know? So, I'm going to continue to think this is true regardless if hard evidence is shown to me and proves otherwise. 4. When the zombie apocalypse happens, this is on my list of places in town to possibly secure and make a fortress out of In reality, I've been here multiple times throughout the years for galas and auctions, cocktail tastings, historical tours, and more (KUDOS to the The Greater Portland Landmarks for doing such an unbelievable job at the preservation of this spot which was added to the National Register of Historical Sites [as of 1973]). This place, to me, feels like a living, breathing relic from the days of Portland's yesteryear. The view of our little seaport town from the cupola of the building is also breathtaking. If you love history and ever have the chance to tour the Custom House... do it. Without hesitation, do it. It's one of those spots that will stay with you forever.

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    United States Custom House
    United States Custom House
    United States Custom House

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    Greater Portland Landmarks

    Greater Portland Landmarks

    4.3
    (4 reviews)
    1.1 km

    I'm a little bit of a history geek, what can I say? I was the kid that relished the opportunity to…read moretalk to my grandparents about their lives growing up, what our community used to be like and look like, what their parents experienced. Finding old photos of towns and cities that I'm familiar with now are unbelievably fascinating, and preserving that which was is something near and dear to my heart. Which is why I'm a little in love with the The Greater Portland Landmarks, the safeguards of Portland's history via buildings, neighborhoods, and outdoor spaces. Through education and advocacy these great stewards of urban conservancy have helped to maintain some amazing spots throughout the city of Resurgam, while thoughtfully bridging the gap from the character of the city that was to the character that the city's beginning to have. I've had the opportunity to explore some of their catalog of public offerings, including Portland Observatory tours (https://www.yelp.com/biz/portland-observatory-portland), Custom House tours (https://www.yelp.com/biz/united-states-custom-house-portland), and a tour of the Homes of Portland's Golden Age (where we walked around the Spring Street Historic District [which was placed on the National Register of Historic Places in '71] and viewed an array of impressive architectural styles throughout the past couple centuries. That's just some of their ongoing events; they also host a lot of other awesome shindigs (like an annual decade-specific themed gala at a large mansion in Portland). The folks who work at GPL are dedicated, passionate, and well-versed in all things Portland. I care deeply about the past, present, and future of this great city, and I feel rest assured that there are others that do so as well!

    Take their tours, donate, support this worthy and well-run cause…read more... In August, I was visiting Portland to eat and relax and look at the water. When my companion suggested (ah-hem, insisted) that we take the Greater Portland Landmarks walking architectural tour, I agreed but had no idea what I was getting into. Like, what? The headquarters or main building is on Spring Street behind the MFA, where I'd been several times already. It's a straight ten-minute walk from the Old Port area, so pretty easy to access. When we got there, we were greeted warmly by the staff and invited inside to wait for the tourists to gather. They allow (and encourage? insist upon?) on-line reservations, which we had. We pad electronically with credit cards using their portable chip reader. It was good to see historic preservation embracing technology. Ten bucks each, totally worth it. Our group of about ten tourists was led by two men, both school teachers, who tag-teamed the direction of the group and the speaking. They were warm and funny and kind and helpful and full of information. When one of them knew that the other was the expert, he'd say, And now XXXX is going to talk about the roofline of Federalist style buildings. Or some such. And the information is transferrable. I was recently in downtown Philadelphia where I was able to identify architectural styles that I learned about in Portland. The walk isn't that long distance-wise because they essentially keep close to the neighborhood around their building but it is strenuous and takes a while because they cover so much, including the Victoria House (from the outside). They encouraged questions and engagements and were helpful and attentive to those with limitations (slow walkers, the deaf, etc). At one point, we Zillowed the price of a house that was on the tour, which connected past and present. The guides even got us an inside tour of the private Cumberland Club. I would do it again. I would do their other tours (including of the Observatory on Munjoy Hill). If I lived in Portland....

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    The beautiful Greater Portland Landmarks building adorned with a Valentine's Day Bandit heart!
    The beautiful Greater Portland Landmarks building adorned with a Valentine's Day Bandit heart!
    Greater Portland Landmarks is located in the William Safford House 1858.

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    Greater Portland Landmarks is located in the William Safford House 1858.
    Portland Observatory

    Portland Observatory

    4.5
    (59 reviews)
    0.9 km

    Lovely visit to the Portland Observatory…read more We had intended on a self-tour but were told that self tours would start at 4:30pm...and that before that time, you would have to take a toured guide up the tower. As there was a scheduled guide about to start soon...we opted to take the guided tour. At that time (mid-week in late August around 12pm) there were only four of us on that tour. Our tour guide, an older woman, was wonderful. As we ascended the tower during the 45-minute tour, we stopped off at each floor and she explained a bit about the tower and its history. Lots of interesting facts! We made it to the top to take in some amazing views of the area. Tours are $10 for adults, $5 for ages 6-16 and free for those 5 and under. The stairs (there are about 100) throughout the tower are spiral-ish...so be careful of your foot placement on the narrowed parts of each step while ascending and descending. Street parking signs can be a bit tricky in the area reading "...no parking on the 1st/2nd/3rd/4th ___day of the month..." Be sure to properly read those signs and park accordingly.

    My plans only have me in town for two days, so I asked my local coworker one sight I had to see…read morewith a short time frame, and was sent here. Just a fun little local tip. The history itself is cool enough: this was a lookout for ships coming into the harbor before radio, and is the oldest currently standing in the USA. But I really appreciated the elevation for getting a good look of the downtown and harbor area, walking around the tower in the breeze and seeing the ocean peaking through the islands in the harbor. Worth the $10 to the top. (Note: the stairs are steep and there's no room inside for an elevator. We're talking large curving internal staircases. Maybe not for those with mobility issues.)

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    Portland Observatory
    Portland Observatory
    Portland Observatory

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    Wicked Walking Tours

    Wicked Walking Tours

    4.6
    (63 reviews)
    0.9 km

    Highly recommended tour in Portland, Maine. Gordon was our…read morevisual storyteller and he captured the attention of my whole family,most notably my skeptical 14 year old son who wanted follow up details to go ghost hunting while we are here. This tour combines ghost stories, local history, comedy, and some pretty fantastic storytelling while getting a nice walk in the evening in. Loved it!

    This past weekend I had the pleasure of visiting Portland, Maine. Aside from some amazing lobstah…read morerolls, what else might you expect out of a historic, coastal New England town? You guessed it.....ghosts. Maine has always fascinated me, ever since I read "Pet Sematary" when I was about 12 years old. In fact, the 1989 version of the movie was just on television. Perhaps no one tackled the Maine accent as well as Fred Gwynn. Ayuh, he nailed his role as the old, weathered, local Maine neighbor, Jud Crandall. (John Lithgow provided a completely different interpretation of Jud in the 2019 version.) It's only appropriate that King, who grew up in Portland, based so many of his novels in the state of Maine. This place is saturated with ghosts, savory characters, and somewhat of a dark history. Last week on my layover I took a Wicked Walking Tour with Gordon, who was absolutely fantastic. Knowledgeable and funny, his theatrical, yet historic tour was well worth my time. Gordon made the tour interactive and got to know each of us on the tour. There was another Lori (spelled differently though), another couple from Cleveland, and some newlyweds amongst our group. We started by learning about some history of the city. Portland buried their dead 18 feet under. Gordon informed us this was to keep the vampires in and the grave robbers out. The Portland Waterfront and the many islands of Casco Bay have stories of pirates, witches, ghosts, fires, and abandoned ships that we learned of throughout the tour. In this particular part of the waterfront a mysterious woman clad in black wanders the dock area, stumbling over lobster traps in search of her sailor. Aside from an occasional wharf rat, there is not much trace of life down here at night. A building that I noticed while walking around the town was the Time and Temperature Building, a building with....you guessed it: the time and temperature displayed on the outside. Gordon talked about this building on our tour. The place is allegedly haunted by a female ghost with fire-engine red hair, who enjoys riding the elevators and who will often play on them, randomly sending them to different floors. Some workers in the building have claimed to have seen an unknown female walking through their offices, and when they follow her or try speaking to her, she vanishes around a corner. Electricians insist that there is nothing wrong with the wiring of the elevators. No one is certain of the back-story here, nor why she does this. Before running through a dark and sinister alley, Gordon pointed out an other creepy building. I don't remember the details, but I remember something about a woman seeing a mermaid, attached to the front of a ship outside her third story window. Apparently the water level used to reach this part of the town and there have been phantom ships, still weathering the storms, to this day. Check out Gordan's tour......I really enjoyed it. His stories are interesting and engaging. Maine is awesome. And the people here are wicked smaht.....

    Photos
    Gordon
    Gordon
    Wicked Walking Tours
    Wicked Walking Tours

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    Maine Day Ventures - foodtours - Updated July 2026

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