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    Tipsy Chocolate Tours

    4.0 (8 reviews)
    Closed 12:30 pm - 2:30 PM

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    7 years ago

    Did a tipsy chocolate tour for a friend's bachelorette and we had a GREAT time!!! Delicious chocolate, tasty wine, and interesting facts!

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    8 years ago

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    Ask the Community - Tipsy Chocolate Tours

    How much For tour?

    Hello and thank you for reaching out. We are still paused for touring at this time. Once our tour sites are back up and running at full capacity and can host small groups in their shops, we'll be running again. Thanks for your patience.

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    Off The Eaten Path - With Franco

    Off The Eaten Path

    4.9(78 reviews)
    1.9 miNorth End

    If you're ever in Boston and want to experience the North End (aka Little Italy) through the…read moreperfect blend of history and cuisine--do yourself a favor and book this food tour! Paula is an incredible guide--an enthusiastic historian with a deep love for the North End, its rich stories, and its vibrant food scene. She brought the neighborhood to life with fascinating facts, local lore, and unforgettable bites from hidden gems we would've never found on our own. We were so lucky to be the only two people who kept our reservation despite the rain, and honestly? It made the experience even more magical. Paula customized the tour to our pace and preferences, and it felt like we were exploring with a friend who knows everything about the area. One unforgettable stop was Ristorante Saraceno, where we met Franco--the owner--who is an absolute joy to interact with. His warm hospitality, legendary food, and impeccable service made us feel right at home. Buon appetito, indeed! I've done food tours in several cities, but this was hands down the best one yet. From the cozy mom-and-pop spots to the authentic flavors and stories, it was a feast for all the senses. You can genuinely feel Paula's passion for this historic neighborhood and its people. Don't miss it!

    We spent our morning with Paula and had an amazing time. If you want to do a food tour, you SHOULD…read moreWANT to do a food tour, pick Paula's. She feeds you tons of good Italian food and desserts. She's a great historian and spent a good time just showing her love for the north end. We will definitely go with her again. She's amazing.

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    Off The Eaten Path
    Off The Eaten Path
    Off The Eaten Path

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    Boston's Politically Incorrect North End Food Tour - The best Sfogliatella I ever had!!

    Boston's Politically Incorrect North End Food Tour

    4.7(184 reviews)
    1.9 miNorth End

    Tony is a true treasure. He loves his neighborhood and it shows. He will take you to places that…read morework to keep the North End a real neighborhood. The food is some of the best I have ever had and they aren't small portions. Come hungry for good food and great stories of what makes the North End a special place. It's a dynamite experience from a guy who is not only a local, but I am pretty convinced he's the unofficial mayor of the neighborhood based on the number of people who said hello (and other stuff unsuitable for small children or church) to him as we walked the narrow streets. You'll even learn some new curse words. Anthony, your tour guide, doesn't hold back what he thinks.

    I have a bone to pick with Politically Incorrect North End Food Tour.... It was so so good that it…read morehas ruined every other food tour for me.... Anthony has set the bar way too high. Now this tour may not be for everyone, as the title of the tour alludes to.. but if you don't mind the random swear word and aren't easily offended, you'll be like me... cracking up for 3 hours straight. And there was one thing I noticed about Anthony that he doesn't advertise, and may try to track me down for saying on here.... But beneath the gruff exterior was the sweetest guy that seemed genuinely interested in sharing his culture, stories, and amazing food with everyone! We started off at a pizza joint where we got a slice of pizza and an arancini ball. I expected the pizza to be good... and it was fantastic. But I am not a huge fan of arancini and this one had peas in it... also something I am not a huge fan.... But hey, I was on a food tour so I was going to try everything! Thank goodness I did, because this arancini was the stuff of dreams. How in the world could something be THAT much better than what high end Italian restaurants advertise? The last time I had an arancini ball was at a restaurant in Hawaii that won "best Italian food in Hawaii".... And it was only so-so. This arancini ball would make me fly 5,000 just to eat it again! Next up was a deli sub, a coffee shop, ravioli, a pastry shop and lastly an affogato (or gelato if you didn't want coffee that late in the day). Based on the food I received, before factoring in all the stories that Anthony shared, I feel the tour was really underpriced. I wish I hadn't done this the tour on my last day, I would have gone back for another round of everything we tried, as well as everything that was recommended. Heck I may have signed up for the tour again just to experience it all over again!

    Photos
    Boston's Politically Incorrect North End Food Tour - The crew with Anthony

    The crew with Anthony

    Boston's Politically Incorrect North End Food Tour - Anthony: actively talking trash throughout the tour, and I loved it! Most people have him the finger when we walked by

    Anthony: actively talking trash throughout the tour, and I loved it! Most people have him the finger when we walked by

    Boston's Politically Incorrect North End Food Tour - Mini lobster roll- forgot the Italian name

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    Mini lobster roll- forgot the Italian name

    Secret Food Tours - Boston - Our tour guide

    Secret Food Tours - Boston

    4.4(22 reviews)
    1.1 mi

    We had a fantastic time with Elizabeth as our tour guide. There were 10 of us and the group in our…read moreWe enjoyed every stop we made starting with the Union Oyster House where we can clam chowder and their corn bread. We added some oysters to our order. Then on to Boston Public Market for lobster roll and a the secret food item. Continued with pizza for Regina Pizzeria. Finished the tour at Caffe Vittoria for their delicious tiramisu. We added additional drinks. I found the tour to be well organized and not rushed. Elizabeth was friendly, informative and entertaining. A total fun time and worth the price for us.

    Was scrolling through Yelp and it suggested I review and IDK how I didnt review the nigh of our…read moretour?! Im so sorry... Our guide (& had I did it that night I prob would have remembered her name) was quite literally the best tour guide I have ever had, at EVERYTHING... I mean just all the tours in life... Im from here - I THOUGHT I knew all the things, and this was a work event and the team is all from here, but we thought it was more a "Food (which it was) Tour" but this gal knew HISTORY - Stuff I didnt even know! But not that she just knew, she had SO MUCH personality, I would literally pay again just to hang with her for the night! With the exception of Dino's I had been to all these places in the past but it was just cool to do it in a different manor. The Food places were fun, the history was great, She was welcoming, knowledgeable and just all around a great person for this job! When in town this is a tour you need (And comfy shoes!)

    Photos
    Secret Food Tours - Boston
    Secret Food Tours - Boston - This woman was literally the best host at anything I've ever been on!!!

    This woman was literally the best host at anything I've ever been on!!!

    Secret Food Tours - Boston

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    Cocktails & Cannoli

    Cocktails & Cannoli

    5.0(21 reviews)
    1.8 miNorth End

    I don't think I have ever experienced a tour quite like this. The main focus of the tour is on…read morecocktails and cannolis, self explanatory. But it also dives into a very intimate history review of Boston's North End. This area of Boston is "everything italian". Through this tour you will experience Italian sweets as well as taste some delicious cocktails that are special to the North End. Patrick is an excellent tour guide. He is very familiar with the area. In addition, you can see the passion that he has for the North End. At the end of the tour he gives excellent recommendations for savory dinner spots. best pizza in town, and can basically answer all things Boston. He also offers private tours. He can accommodate for any dietary restriction. My husband is vegetarian and does not eat eggs, and Patrick was able to find some amazing Italian sweets for him. It is about a 2 hour walking toward. You get all your steps in so you won't feel guilty about the delicious things that you eat. It is an easy walk, so don't let the duration scare you off. I 1000% recommend this tour. Book directly through his website. He's quick to respond if you have any questions. Enjoy!

    We had the best time with Pat! An amazing value - the cost was more than worth the drinks and food…read morewe got to have. Not to mention Pat's knowledge of the North End, the cute places we got to experience, and his stories along the way. If you want to try the best cannoli in town skip the lines and let Pat be your guide - no waiting involved! Cannot say enough good things. Cin-cin!

    Photos
    Cocktails & Cannoli - Pistachio martini!

    Pistachio martini!

    Cocktails & Cannoli
    Cocktails & Cannoli

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    Free Tours By Foot

    Free Tours By Foot

    4.9(192 reviews)
    2.6 miJamaica Plain

    We had a great North End tour with David today. In spite of the rain throughout the tour David kept…read moreus entertained along with providing great and interesting detail throughout the tour. David's appreciation for food made the tour that much better. We were definitely ready to eat some great North end food by the end of the tour. Along with David's entertaining stories he also shared a very moving story when telling us about the beautifully designed Holocaust memorial. Free Tours and David are highly recommended.

    4.5 stars. We…read morejoined the Free tours by foot in NOLA/ Garden District back in Feb, had a great experience and was glad to find out there is one in Boston as well. Signing up for the tour was easy enough though I don't really like the idea of paying the (optional) fee via PayPal. For some reason when I did that in New Orleans, it automatically created a new PayPal account for me, based on the email address I used. (Even though it says you don't need a PayPal account...) But this time when I attempted to use the same email to pay, it just wouldn't go through despite resetting the password and what not. Ended up asking hubby to pay with his PayPal. Quite a hassle. Other than that, our guide, Brian, was hilarious and passionate about educating us and I had a great time. We took the tour on Mother's Day and half of the 25 or so customers were from Europe. I think maybe there is a little language barrier as not everyone laughed at Brian's jokes. Plus it was a super windy and cold day and some just wanna go back to bed I guess. The tour was about 1 hour 45 mins. It really didn't walk far, maybe 1-1.5 miles. But I truly enjoyed the story telling. Highly recommend.

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    Free Tours By Foot
    Free Tours By Foot
    Free Tours By Foot

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    Tipsy Chocolate Tours - foodtours - Updated May 2026

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