Italy Tours

It’s time for the Authentic Italian Experience of your lifetime!

Your Backstage pass to Italy comes with some perks…



Remember that whirlwind Contiki tour you took with 50 other guests? That won’t be us! Instead, you’ll feel like you’re traveling among friends – not a participant on a high school field trip.

Unpack Once

No 5 am wake-up calls, sleeping in overnight trains, and constantly changing hotels every other day.  We take vacation relaxation very seriously! De-stress and relax knowing you have the luxury of unpacking once and slowing down so you can dive deep into Italy’s “La Dolce Vita”.

“This is the tour for you if you want to avoid the touristy part of Italy, experience the intimacy of a small group italy tour & gain insight into the local Italian culture & cuisine”

Ron Ferri, Victoria, BC, Canada

If you want to relax and enjoy a tour with a personalized touch without packing & unpacking everyday, this is the perfect solution.

Belinda Reilly, Brisbane, Australia

“If you’re tired of travelling with busloads of fellow tourists Chantelle and Giovanni have put together the perfect solution.”

Belinda Reilly, Brisbane, Australia

We ‘re not just locals and Italy experts, we’re travellers of Italy, too! You’re our honorary guest. And we’re your fun and fabulous Italian friends.  We get you, know what you want to see and experience, and know the best ways to make that happen! From the moment we welcome you on tour to our final goodbyes, we’ll be there every step of the way.

Exclusive Italian Travel Intel

Forget struggling about the best way to get from point A to B. Swipe our insider advice for pre and post-trip planning! With us in your back pocket all you need to do is write an email and click send. Get access to insider knowledge, bilingual guides, and personal relationships that allow you to experience Italy like it is your home.   

From the moment I was greeted by Chantelle & Giovanni at the airport, I felt like a friend. A friend that they looked out for and introduced to their local Italian friends who were also lovely, friendly, and local experts.”

Stephany Branham, Columbia, South Carolina, USA

The experience provided by Giovanni and Chantelle is second to none.  You will not find the amazing places, wineries and food without them. The quality and location of the hotel was perfect! a good example of the quality of the people they have partnered with. Can’t recommend it highly enough!

Lee Farrington, Melbourne, Australia

“I felt like I was traveling with a couple of good friends, rather than with a small group tour.  Giovanni & Chantelle made me feel very welcomed

Juliana Yu, Victoria, BC, Canada

Giovanni is an Italian native of Ascoli schooled in the US and Canada. His English is fluent. Chantelle is a Canadian expat who also speaks Italian. So, you get local expertise and great service!

Rachel Stender, Bethseda, Washington, DC

The Gold Standard

We don’t subcontract out. In Italy food & culture go hand-in-hand. That’s the real Italy. We’ve personally tried, tasted and tested every single experience ensuring quality and authenticity.  If it doesn’t meet our personal Stamp of Approval, it won’t be on your Italy tour!  Zero tourist traps, subpar service, or second rate Italian food.

Your backstage pass isn’t off limits because you have to dine gluten-free.  On select Italy tours, get a behind-the-scenes look at genuine everyday G-Free Italian lifestyle. Now you can tour Italy, have your GF cake and eat it, too!

“The food on their Italy tours was amazing! Giovanni and Chantelle have picked the best places in the region to eat, explore and visit”

Juliana Yu, Victoria, BC, Canada

“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!”

Nicole Hunter, Nova Scotia, Canada

“the food experience was Excellent! as was the accommodation and all the wonderful meals in one of the most picturesque partS of italy.”

Ronald Ferri, victoria, BC, Canada

Here’s how we can help you uncover the real Italy


Grab Your backstage pass to the real Italy with our intimate Small Group Italy tours of 8 days or 10 days in length.


Enjoy a behind the scenes look at the real Italy without the fear of vacation glutenation.  Chantelle is gluten-free and she’s got your back!

“after my tour, I felt relaxed. the warmth of the locals, the authentic culinary experiences, gorgeous medieval villages, the cooking classes: all of these were the perfect ingredients for a successful vacation.”

Juliana yu, victoria, BC, Canada


about your tour with us!

small group italy tours and trips

Support Small Business

When you book your Italy tour with us you’ll support small local businesses. From your 4-star boutique accommodations, multi-generational wineries, and family-run restaurants, each and every partner we work with calls our territory home. 


small group food and wine italy tours

Connect with the locals

You’ll come face-to-face with the people that love and live in our territory.  Every local expert from the talented chefs to farmers and winemakers are locals you’ll meet with when you travel with us.  Plus, you’re helping many of these passionate locals return home (like Giovanni) and revive Italy’s hidden regions. 

small group food and wine italy tours

Visit Italy’s Hidden Gems

By skipping the overcrowded sites for a slice of authentic Italy you’ll help ease the pressure on the effects of over tourism on Italy’s big cities and major tourist sites. Did we mention you can visit Italy’s Largest Medieval fortress, sip your morning espresso at Ernst Hemingway’s favourite cafe and forage for truffles with Jamie Oliver’s truffle hunter? 

“Giovanni & Chantelle are the perfect guides to translate the Italian experience”

“Traveling like a local is not straight-forward. This type of experience requires someone on the inside who can guide you – and that’s where The Italian On Tour®‘s Italy tours step in.”


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