Does your idea of the perfect Italian vacation include vast rolling hills, verdant vineyards, picturesque beaches, rich, vibrant culture and rustic cuisine? If so, look no further than the beautiful country of Italy! Attracting over 60 million tourists a year, maybe you’ve been hesitant to visit Italy because of the crowds or you’ve “done Italy” and don’t know where to travel next – you’ve come to the right place! Filled with numerous regions and the greatest number of UNESCO heritage sites in the entire world, each region of Italy is like its very own country to be discovered, but it’s how you travel it that matters. Read on to uncover how a small group Italy tour with The Italian On Tour® is the ultimate solution to skipping the tourist traps, taking the guesswork out of your Italian vacation and having the authentic Italian experience you’ve always dreamed of

Trade overcrowded attractions for off-the-beaten path locations, curated experiences and (actually) authentic Italian cuisine, then pop the Prosecco, because traveling on a small group Italy tour with The Italian On Tour® is the perfect solution for you!

A truly intimate Italian experience

Before booking any small group Italy tour, it’s important to do your research and understand the ins & outs of the tour you’re planning to take. One not-so-ideal experience that many travelers encounter upon arriving in Italy for their small group tour, is that their “small group” isn’t so small after all. While some of the commercial Italian tour companies market their tours as a small group environment, these tours often host groups of up to 30 people. Traveling with a group of this size unfortunately gives you very limited access to your tour hosts and leaves you feeling like you’re just another number, only to be watching on the sidelines and not actually getting to fully immerse yourself in the local culture leaving you missing out on experiencing the real Italy.

There’s no better way than to experience the local culture than through getting to know its people. That’s  why The Italian On Tour defines its small group tours as a maximum of 12 guests, ensuring you’ll never feel like a teenager on a high school field trip! One of our biggest priorities when welcoming you to our home country is creating an intimate, personalized experience to ensure that you feel a genuine sense of comfort and connection. Even before you officially book your small group Italian tour, we’re here to share our vast knowledge of Italy, give you our best tourist etiquette tips, advise you on what to pack, and even guide you on how to book your flight. Once you arrive in Italy, we’ll travel with you throughout your entire small group tour, guiding you through every experience and answering all your questions as if you were exploring with your Italian best friends.

Chantelle and Giovanni are a very insightful, educated, cultured husband-wife team. From the moment they greeted me at the airport, I felt like a friend. A friend they looked out for and introduced to their local Italian friends who were also lovely, friendly… and local experts.“


Columbia, South Carolina, USA

The best part? You’ll only need to unpack once on your small group tour with The Italian On Tour®! Instead of dealing with 5am wake-up calls, sleeping in overnight trains, and changing hotels everyday, our tours allow you to “plant your roots” for the entirety of your stay in your 4-star boutique accommodations that have been tried, tested and personally selected by us!   

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Experience Italy without the crowds

Let’s face it: no one wants to travel to an exciting destination abroad, only to be crammed like sardines on a full coach bus and spending hours in line under the heat of the sun waiting to enter packed tourist attractions. Instead you want to skip the lines, enjoy the comfort of private vehicles, and roll up feeling relaxed by knowing everything is taken care of. That’s part of the beauty of embarking on a small group Italy tour with The Italian On Tour®.

Not only will you get to experience Italy without the crowds and visit some lesser-explored locations, such as Ascoli Piceno, known for its travertine Renaissance piazzas and rich culinary & cultural history, some of the Best Beaches in Italy, UNESCO Palaces, and private dining experiences in World-class wine country (all of which you can experience on select tours), but you’ll be able to completely unwind knowing that everything is taken care of, allowing you to get the most out of your Italian vacation when you join us on tour.

Venturing off-the-beaten-paths of Rome, Venice, Tuscany, and Florence to discover Italy’s best hidden gems, you have the opportunity to enjoy a wealth of unique experiences steeped in Italian culture and tradition ones that you just won’t find when you book your Italian vacation with the big tour companies and major travel agencies. The Italian On Tour® curates, tries, tests and tastes everything you’ll experience on our exclusive small group Italy itineraries.

When you grab your seat on a The Italian On Tour® small group Italy tour you’ll get access to itineraries and experiences you simply cannot get anywhere else. The Italian On Tour®’s perfect balance of free time and activities will have you living like a local as you stroll through charming medieval villages nestled amidst the breathtaking Italian countryside, truffle hunt with one of Jamie Oliver’s truffle hunters, or sip world-renowned wines in sun-soaked vineyards at Palladio Villas that have producing wine for over 500 years!

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Italy insider knowledge and planning

Even if you’re the type-A, “itinerary-planned-to-a-tee” style of traveler, venturing abroad on your own to a large country with the world’s highest number of UNESCO heritage sites where you don’t know the lingo or local travel experts can be intimidating and overwhelming. Even though you want to get off the beaten path, knowing what sights are actually worth seeing often leads many travelers, like yourself, to stick to the more tourist-heavy areas of Rome, Tuscany, Florence, Sicily, Venice, Milan, and Cinque Terre.

Secretly, you know that experiencing Italy like a local requires more than just renting a car, TripAdvisor reviews and getting off the main tourist track.  You need someone on the inside to translate the Italian experience. That’s where The Italian On Tour®’s Small Group Italy Tours step in!

“Giovanni and Chantelle are dynamic and charming and have tapped into their network to provide exclusive experiences for their guests. Travel experts with a passion for the food, wine and art, they are the perfect guides to translate the Italian experience for their guests and help introduce them to this corner of Italy.”

Forbes, 2019

Embarking on a tour hosted by two Italian locals will give you access to the hassle-free planning and insider knowledge that a Google search simply can’t offer. Rather than going it alone and trying to figure out all the logistics, or opting into one of the commercial Italy group tours and becoming just another number, our small group tours give you a front row seat to unique experiences and the perfect balance of relaxation, exploration and fun.

“You can really feel the love and care they put into their business and getting to know Giovanni  & Chantelle was a definite value add.”

Rachel Ruvo

North Carolina, USA

Unlike the big tours that tend to only pass through the often mediocre, “popular on Instagram” attractions, restaurants and wineries, we’ve personally vetted and curated every experience on our tours to ensure it meets our Gold Standard. We’ll get you a place at the dinner table of a multi-generational Italian family, send you on a private tour of a boutique Gambero-Rosso award-winning winery with the winemaker himself, and secure your front row seat to a glass-blowing demonstration on the Island of Murano on select tours, all possible because we’ve built genuine relationships with the Italian artisans, local chefs, multi-generational farmers, award-winning cheese producers, organic honey makers, and small-scale winemakers that you visit on our tours.

Even if you’re coming to Italy as a gluten-free diner, we’ve got you covered on select tours! Our founder has spent a lifetime traveling Italy gluten-free. That’s why we’ve spent our time carefully selecting restaurants and experiences that will allow you to live your best gluten-free life while still enjoying authentic pizza, pasta and wine that is celiac safe on your vacation to Italy. No mediocre GF meals here; one of our past guests even said, “the gluten-free food and wine was amazing! I highly recommend their Italy tours if you are unsure you can enjoy amazing cuisine in Italy on a gluten-free diet!”

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Itineraries you won’t find anywhere else

The vast majority of small group tour operators in Italy follow outdated industry standards and design itineraries by plucking experiences from cookie-cutter activities and tourist-heavy attractions that are available to every single tour operator out there. Seeing a gap in the industry, The Italian On Tour® founders, Giovanni and Chantelle, set out to design tours that allow you to truly immerse yourself in the local culture. 

To ensure that your trip to Italy is the life-changing vacation you’ve always dreamed about, we’ve personally crafted every single experience you’ll have on your small group Italy trip with The Italian On Tour®. With over 35 years combined experience in Italian gourmet food, wine and Italy travel, we truly get you, and understand how you want to experience Italy, ensuring your trip is seamless by personally hosting every single tour. The love, care and attention to detail that we put into each of our itineraries, from before you arrive until the moment you depart, is just one of the many reasons food and wine lovers, like yourself, choose to travel Italy with The Italian On Tour®. In fact, many of our previous guests have said their time with us made them feel like family, and they return again & again to join us on each new Italy itinerary we design for future tours! 

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Connections with like-minded travelers 

Italian culture is all about togetherness, and traveling Italy is no exception! The Italian On Tour® attracts travelers that come to Italy with a common love for food, wine and experiencing a new culture an experience that is best had in group format, where you can share your passions with your fellow tour-goers and create lasting memories together. By booking a small group tour with The Italian On Tour®, you’ll have the opportunity to connect with like-minded travelers who share your enthusiasm for Italy’s rich heritage and culinary delights.

Whether you’re a solo traveler looking to make new friends, a couple seeking a romantic getaway, or celebrating one of your life’s biggest milestones, our small group tours provide the perfect setting for forging connections and fostering camaraderie. With a maximum of 12 guests, you’ll have ample opportunities to socialize, exchange travel stories, and bond over shared experiences. We believe that the people you meet along the way can greatly enhance your travel experience, and our tours are designed to facilitate those meaningful connections.

From indulging in authentic Italian meals together to exploring hidden gems and engaging in cultural activities, you’ll have the chance to build friendships that can last a lifetime. Our guests often form tight-knit groups that continue to stay in touch even after the tour ends, planning future trips together or simply reminiscing about their unforgettable adventures in Italy.

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Environmentally and socially conscious tours

If you ask us, part of experiencing Italy like a local means planning your vacation in a way that’s conscious of the environment and respectful of the residents, which is something that the big tour companies lack. They consistently use “Green-washing” methods of marketing to appear environmentally conscious, when quite frankly, there’s no way of getting around the fact that a Big Buses have a larger carbon footprint, and the companies that have the capacities to service large groups are not small family-run producers or locally-owned boutique accommodations. A major misconception around those large tours – one that’s often pushed by the commercial tour companies in Italy – is that these high-capacity group tours are more “environmentally sustainable” because they fit their travelers on one big coach bus, but this just isn’t the case! When those buses are filled to capacity with tourists and taken to heavily visited areas, the effects of over-tourism are felt by the locals, by way of higher rent and food prices that end up driving them out of the areas they call home.

On the other hand, The Italian On Tour®’s small group Italy tours prioritize environmental and social responsibility, while demonstrating genuine respect for the locals — because we are the locals! We steer clear of areas overrun with tourism and travel in small groups using passenger vans rather than coach buses or mini-buses. By fostering close collaborations with the Italian locals and small businesses we visit, we ensure that our tours have a positive impact on the local economies instead of causing harm.

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Embark on the Italian vacation of a lifetime

Whether you’re an adventurous soul looking for unique places to visit in Italy that you can’t find on your own, a retiree looking for Italian tours for travelers over 50, or a romantic dreamer looking for the best places to go in Italy for couples, The Italian On Tour®’s small group tours have something for everyone dreaming of experiencing Italy like a local!

Forgo the exhausting planning and logistical nightmares, unpack only once, and arrive in Italy as our honored guest and friend when you join us on tour. You’ll experience the real Italy with The Italian On Tour®’s boutique small group tours for food and wine lovers.

Dates and space are limited to ensure that our small group tours really do remain small and allow you to experience the highlights of each season, so click here to explore your Italian itinerary and reserve your preferred dates today!

“A Life-changing Italy trip!”

What an amazing experience!  I’ve been to Europe three times before and this was easily my favorite trip!


Seneca Falls, New York, USA

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