Come hungry for this unique Boston tour! A person could spend a lifetime in Boston's Little Italy and still not get to taste all the delicious food that this quaint, European-style enclave has to offer. This neighborhood alone has over 45 restaurants serving Pizza - let us show you the best of the best!
This walking tour explores Boston's Little Italy, or what locals call "the North End". Included on tour are stops at three different Pizzeria's, tasting a slice at each location. We'll stop by a few old pubs for a cold one to wash it down and along the way hear some strange stories from Boston's oldest neighborhood, settled in 1630!
This unique tour can also be tailored for Family groups, Church groups, Birthday Parties, and Pizza Crawl events - just message me to set up a private tour.
- Three slices of delicious pizza
- Fun facts about Pizza and the North End
- Exploration of Boston's oldest neighborhood
Must be 21 or over to drink, bring proper ID. Be aware that there are pub stops on this tour. Alcoholic beverages are not included in the tour, nor are other beverages so please bring your own bottled water as this is a walking tour and it gets hot in the summer. Wear comfortable shoes and weather appropriate clothing. Tour will be cancelled in the event of rain or other harsh conditions. Come ready to enjoy Boston's oldest neighborhood and some great pizza!
Meeting Place50 Salem Street, Boston, MA 02113
ReviewsRate this tour!
★★★★★ Staff Summer Outing by Sarah W.
Our office was looking for something out of the ordinary for our summer outing this year when we came across this tour. We had a wonderful time sampling pizza and beer. As Jimbo guided us through the North End, he pointed out unique areas of interest and gave us tidbits of information that even those from Boston were unaware of. The pizza was delicious and well-timed and everyone enjoyed socializing over a pint. We would highly recommend this tour to any group looking for a little adventure in the North End. Make sure to bring your sense of humor & don’t forget to tip. Thanks again Jimbo!
★✩✩✩✩ Tour kept getting cancelled by Michelle D.
I was looking forward to taking this tour and twice it was cancelled on me. The first time was because there wasn't enough people. I was able to reschedule which was great. But the second time, I received an email saying that the tour would take place. I drove into Boston, waited where we were to meet with other people taking the tour. After 15 minutes of waiting we realized an email was send about an hour before that the tour was cancelled. It was a huge disappointment and very aggravating that we drove in for nothing. A phone call would have been nice instead of an email. It's too bad because now I have no desire to try and schedule for another tour in fear it will be cancelled yet again.
Personal recommendation from Jannel C.
Jim and I met three years ago at a Les Claypool concert. Our amazing taste in music, outgoing personalities, and the fact that he is from Plymouth and knew my cousin started our friendship. If you want to have a good time Jim is definately the guy you want to hang out with!
Personal recommendation from Chris K.
A tour guide (or tourist guide) provides assistance, information and cultural, historical and contemporary heritage interpretation to people on organized tours, individual clients, educational establishments, at religious and historical sites, museums, and at venues of other significant interest. Jimbo Meets all criteria for the occupation "Tour Guide" I have known jim for about 7 years and I can honestly say I have never had anything bad to say about him. I do know he is passionate about his work and everyone I know that has been on his tours loved it. I have never been on his professional tour but I can say I have hung out with jim many times and they were quite the experiences " fun money couldn't buy". So I know Jim AKA Jimbo can give you the tour of your life.
Personal recommendation from Kristen H.
Awesome guy, really cool down to earth & knows how to show you a good time. Definitely knows his way around town!
Personal recommendation from carly g.
I first encountered Jim when I moved back to Boston from London. I was looking for new friends and and fun times in a city that I love and haven't spent nearly enough time in... and he is just the right guy. Immediately when I met first him I felt at ease and knew we were going to have a great time. He's knowledgeable, fun, humble, and he really cares about whether or not the people he is with are having fun. He is charismatically loud in the best way possible and he has a great sense or humor which allows for great entertainment. Most importantly it helps that he is super-duper attractive. Much love!
Personal recommendation from Lois M.
When we were in Boston, we wanted to see some of the city. Our tour guide was Captain Jimbo. He was wonderful. He helped us navigate our Sedway all over the place. He was very charming, funny and just a lot of fun. If you want to have a really good time sight seeing, Captain Jimbo is your man.
Personal recommendation from Rebecca R.
Jim has the perfect personality for a tour guide! He is outgoing, personable and likes to have fun. He is very knowledgeable of the Boston area and would be the best person to have to show you around. I have known Jim since high school and I know that he is intelligent, hard working and enjoyable enough to tour a city with! Take a tour with Jim and I know you'll learn things and have fun! =)
Personal recommendation from Mary D.
Cap. Jimbo and I go way back to one of the 1st tours I ever took in Boston. He's a rock star host and feels like a true member of your entourage as a hilariously well-rounded true Bostonian taking you on a phenomenal adventure through a fantastic city. If you are looking for a new, unique and unforgettable Boston experience, you have to jump on board with Cap Jimbo. He never disappoints!!!
Personal recommendation from Michael G.
I met Jimbo 18 years ago in grade school. I just moved to town and didn't have any friends yet, Jim was the first person to approach me. Its funny now to look back at that time, Jim showed me the ropes and i made a few friends in the process. If it wasn't for Jim's friendly and cartoonish personality, i may have dreaded my new school. Jim is one of a kind good hearted guy and a great tour guide. You'll never forget Jimbo!
Personal recommendation from Joe A.
capt: JImbo Knows the city of Boston. I enjoyed his comical wit, and expertise. He is reliable and everyone on our tour had a wonderful time. i love the history in Boston, and had some questions for jimbo that he was thrilled to answer. I recommend jIm as your tour guide, because he simply is the best at what he does. Best Regards Captain !
Personal recommendation from Troy H.
I met Ji m at a dive bar in the Cambridge section of town about a year ago. I am from Pa. and I was sitting at this bar (I come to Boston once a month on business) and Jim sat down and in 10 minutes we were friends. The following night Jim took me on a tour of down town Boston (mostly dive bars) I had a great night. I have been on subsequent dive tours with Jimbo. Jim is one of the wittiest people I have ever met. He is current, funny and a down right cool dude. I HIGHLY RECOMMEND THIS GUY to other HipHost members Troy Heikes
Personal recommendation from jacky g.
im is a great traveler thats how we met he was traveling with a sister promotional company for starbucks an they were traveling across ma doing promo for new frappuccino i worked at store in pittfield ma an helped restock him with extra supplies...but was immedietly drawn to his great personality that was like 6 or 7 yrs ago an we have been great friends ever since. We then met up out in boston where i had never been an he gave me a great tour of the awesome city he was a great host an totally enertaining as well as knowledgeable of the ins an outs of the great city it was awesome like jim.....i think he would be great for hip host he was born to host an tour an be with people i would totally give him an oportunity to wow others as he did me.
Personal recommendation from James K.
One of the best guides I've had. Knows his stuff and the enthusiasm made it a great experience. Fun and worth the money. Thanks Jim!
Personal recommendation from Alex P.
Jim is the perfect tour guide!!! He's an unbelievably entertaining and funny guy; but also incredibly intelligent and hard working. He's always been driven and motivated; ever since I met him in high school. We spent many days and nights running around Boston together and I can certainly say he knows his way around. He's been all over the country but always comes back home: Boston. His love for the city and for people is apparent. I'm proud to call him a friend; and I know you'd be stoked to have him as a tour guide. :)
Personal recommendation from Chris M.
Captain Jimbo has to be THE best tour guide I've had. I normally go exploring myself but Jim really shed a new light on Ol' Bean Town. I've discovered some amazing "hole in the wall" places to eat that I would have never found on my own. If I could give star ratings, a 5 out of 5 wouldn't do it any justice.
Personal recommendation from Heather H.
I have known Jim for over a year now, we met on a vacation in Long Island and have been in touch ever since and there is a reason for that. Jim is one of he nicest and understand people I have met. He listens to you all while giving you some of the best laughs of your life. I went to visit Jim in Boston a couple of times and I got the best tour. Jim made he tour to what he know I would like. He has a great way of reading people and knowing what to show them based on their personality. He know facts upon facts and made it fun. Every time one of my friends visit Boston, I hook them up with Jim because I know he'll never disappoint anyone.
Personal recommendation from Angell L.
My Name is Angell Love..and I have known Jim for more than 10 years now. He is definitely a one of a kind person. He is very good at what he does and can have a good time while he's doing it and not bore you in the process. If I could pick anyone to give me a tour of anywhere it would be Jim because not only would it be a great tour but like I said he would make a blast while your there. Jim is a good friend, a good person , and all around a good guy I would recommend him to anyone I'm definitely glad to call him my friend I wish him the best of luck however I'm sure he don't need it because what ever he does he does it awesome !!
Personal recommendation from Mj J.
Jim is a witty and knowlegable guy that should have his own show on the Travel channel. He is easy going and despite his over-zealous affinity for all things bacon :-),he ensures that everyone is having a fun memorable time. His insight into Boston history and culture goes well beyond what you see in guide books and I highly recommend him for your next foray into the Hub.
Personal recommendation from Amy C.
From the moment I met Jimbo, I was laughing. We met about 5 years ago at a bar through a mutual friend. I specifically remember Jimbo was the man who was always saying the wildest crazy things, the things others, including myself, thought, but would never dare say aloud. From innovative and hilarious tours to cooking up the best meal you may ever have, Jimbo is the man who will keep you laughing, smiling, and excited about life.
Personal recommendation from Brian D.
Knowing Jimbo as well as I do, I say it's borderline insane to not use him as your tour guide. He is funny, smart, informative, and charming. He knows how to entertain while teaching you about the city life and surrounding areas. Jimbo is probably the most outgoing person I know, and he does it without having that need for attention. He is authentically entertaining, creatively funny, and genuinely professional. He doesn't have that fake-salesman-who-only-laughs-to-make-you-feel-comfortable approach; Jimbo is the real deal.
Personal recommendation from Mike S.
Jimbo is one of the most energetic and fun tour guides I have ever encountered in any city. Not only is he incredibly knowledgeable on topics such as Boston history, great places for food and drink, and info on your favorite Boston team, he does it in a way that is accessible, exciting, and tremendously entertaining. I won't tour Boston without Captain Jimbo.
Personal recommendation from Gail W.
I've known Jim for many years through family. He's always had a great sense of humor and a very quick wit. When I think of Jim I think of someone extremely intelligent as well as entertaining. I think "entertaining" is his middle name. In high school he was a member of DECA and I think it's part of why he is so good at marketing and selling himself and Boston. On tours he's all about his party not only learning the history of the places they see, but also having a great time with memories that they will speak of for many years and say, "I was on this tour one time and I'll never forget when ..." Now I think that speaks loudly about a tour guide when someone remembers the tour years later. There is some Irish blood running through his veins and as such he may be prone to embellishing some historical facts. But that's why everyone has such a great time with Jim and loves his tours. Jim has never known a stranger and is extremely personable. He loves BOSTON and it shows with his high energy and enthusiasm that will keep his group entertained from start to finish. You will never go wrong with Jim as your tour guide.
Personal recommendation from Amy G.
Captain Jimbo is a brilliant mix of knowledge and humor which makes for a fun day in the city! His passion for Boston, life and people spills over into each and every tour. I would recommend out-of-towners not to miss out on a personal tour and for Bostonians to take time out of your busy schedules to fall in love all over again with Boston!
Personal recommendation from Holly A.
I have known Jim and Jimbo for over 15 year, both personally and professionally :) Personally, his love of Boston, unique personality and witty humor provide for a great experience while touring. Professionally he takes pride in everything he touches. The level of passion he has for what he does come through in your experience. Jimbo will make you feel very welcome to Boston, wether you are visiting from another town, state or country. You will learn and experience things about the city with Jim that you won't find on any other tour. An overall great guy and hard worker I would recommend his tour guide skills to anyone. Top nouch in my book.
Personal recommendation from Bill H.
I've known Jim for just over 20 years now and in all that time I've learned one very important thing: Trust in Jim and good things happen............ I've gone on many an epic adventure with this guy whether it's some far off locale or even right here in our own backyard. This man has an encyclopaediac knowledge of the backalleys, burgerjoints, and barrooms of this here fine city. Give him a try and you won't be let down!
Personal recommendation from Jersey S.
Jim is a Bostoninan to the core. He knows the in and outs of any show, event, or venue. He is an amazingly animated tour guide, and an a great dude. I've had the pleasure of knowing Jim for a couple years, and when I was new to the area, he showed me around the ropes. He is a jamband fanatic, which we have in common, as well as our desire to boogie. I recommend him for this since he is the epitome of a "hip host!" He style, class, and moves, and I would vote him to the office if I could ; )
Personal recommendation from Matt C.
I have known Jim for around 20 years now. He is great man with a lot of life experience. Jim has been all over the place in terms of travel, but he cannot seem to leave Massachusetts, mainly Boston. Basically he can't stay away from his true home. Jim is a very energetic person with more enthusiasm for life than anyone I know. I would highly recommend Jim!
Personal recommendation from Paul S.
"Captain Jimbo is just simply the BEST!!!" Not only is he well educated and giving everybody interesting facts but he has you in stitches the whole time. This is one hilarious captain. If your a tourist thats looking to see the city and laugh until your gut burst go see Captain Jimbo.
Personal recommendation from Jess L.
I'm pretty excited to recommend Jimbo as a tour guide. In my 5 years of knowing him, he's taken me on countless walks about Boston - each one better than the last! He’s enthusiastic and professional and knows the city inside and out. You’ll learn a ton of history and some fun quirky facts about the city. And you’ll have a great time along the way!
Personal recommendation from Andrew L.
I've known Jim for several years now, and I can attest to his energy and enthusiasm for the city of Boston. Every time we meet, I'm greeted with new stories and anecdotes about the tours that he conducts, and he's as authentic as it gets!
Personal recommendation from seth b.
I've known Jim for a few years now and he's a good guy to know. We met through friends at various parties and got to know each other through a mutual love for food, fun and travel. Jim is quick witted and full of stories. This is his calling!
Personal recommendation from Jesse M.
I had such a blast when Jim showed my wife and I around Boston. He really showed me a side of Boston that I wasn't quite aware of. Highly recommended. Have a great tour!
Personal recommendation from Wayne C.
Jimbo worked for me as a guide at the Segway tour company I managed. He was BY FAR the best tour guide we had. I took several tours with Jim and always learned something new each time. We received more compliments for him than any other guide--and his tips showed it! He connects very well with his guests and his humor and wit help history become fun again. Any time we had VIP guests, Jim always was the man I sent to give the tour. Trust me, if you want a great tour of Boston, Jimbo is your man.
Personal recommendation from Robert P.
Having known Jim for many, many years there was no surprise when he told me he was going to start showing people the great city of Boston! Jim has an eccentric, loud, knowledgeable, outgoing personality and he knows how to have a lot of fun! Having taken many a pub tour or two before, I can assure you; Jim will meet and exceed your expectations! His presentation as a tour guide will be like no other experience you’ve ever had! Cheers!
Personal recommendation from Jeffrey M.
I've known this lovable, enjoyable, and charismatic guy for a few years now. I can safely say there is NO ONE in the city of Boston that can take you on a tour, and teach you a thing or two, all the while guaranteeing an unforgettable experience. If you’re looking to get to know Boston, but not be bored with one of the hundreds of generic Benjamin Franklin impersonators out there, Captain Jimbo is your man!
Personal recommendation from Chris R.
I have to say that Jimbo is the best tour guide i have had hands down. He was not only knowledgeable about the whole Boston area, he catered to what we wanted specifically and made our experience unique. Aside for that he is hilarious, and so friendly. I don't think there is a better way to see Boston.
Personal recommendation from Martin E.
In the past, Jim and I have both worked as guides for a very popular Boston tour company. You may ask - how can I possibly recommend my competition? Jimbo is simply a GREAT Boston tour guide - that's how! Jim mixes food, fun & facts in the most unique way. I can't wait to try his "Grub and Pub Crawl"!!
Personal recommendation from William Z.
Went on a Pub and Grub tour with Jimbo and had a great time. He was a very personable tour guide and made sure everyone had a good time. We will definitely be doing the frisby golf tour in the near future.
Personal recommendation from Mark H.
We (three generations) just got back from the pizza tour with Jim, who showed us some very cool and out-of-the-way spots. A good time was had by all.
- Location: Boston
- Occupation: Tour Guide
- Favorite Places: Bahston!
- Languages: English
- About me: Hey Now! My name is Jim, but on tour I'm known as Jimbo. I've worked as a tour guide in Boston for quite some time now, and have been told by numerous people that I give the best tour they've ever taken, in any city! Search "Captain Jimbo" on Facebook to find over 100 fans of my tours, some stories, and cool videos! Heres a link to my new facebook page! www.facebook.com/tourmasterjimbo For groups of all sizes and styles, and from history, to food and drink, and all things Boston Sports, I'm the best Boston has to offer, and can't wait to help tailor-make a tour for you! Im currently offering a trio of terrific tours: The Grub and Pub Crawl (featuring my personal favorite pubs and grubs, this is not to be missed!) The Downtown DiscGolf Tour (18 holes of downtown discin fun!) and the Pizza, Beer, and Paul Revere Tour (Bostons best pizza, great beers, and good ol' Paul Revere!) Check them all out!