7 day ITALIAN VACATION for food & wine lovers

Italy undiscovered


Your ticket to being italian for a week.

Escape the crowds & get a backstage pass to experiencing Italy’s hidden regions of Le marche & abruzzo like a local

As seen in:



the italian on tour

Leave the Umbrella Waving Tour Guide (+ Crowded Bus) Behind and Sip Sangiovese in the Vineyard With…


…and explore Italy’s hidden regions like a local on this 7-day adventure.

For 6 nights, indulge in personalized service, authentic cuisine and real Italian life.  

Plus, exclusively curated experiences & day trips (including some of Italy’s most beautiful villages, local farmers & winemakers).


“This trip was exactly what we wanted and gave a glimpse into real Italian life.”


North Carolina, USA


“This is not like other tours.  On this personally led tour you’ll get amazing service and gain local insight into a part of Italy not really known by tourists”


California, USA

If you could connect with (and eat like!) the locals all while experiencing genuine Italian life –

without ever having to lift a finger

(or worrying about the lingo)

…would you give yourself that chance?

Or, would you keep on…

🚫 Feeling overwhelmed with planning your Italian vacation while worrying about the logistics & guessing if the activities you’ve planned are money well spent or even worth your time? 

🚫 Rolling up in a coach bus packed with 50 people on a whirlwind “Ultimate Italy” tour only to be exhausted from fighting through lines, and wasting your precious vacation days on a crowded bus?

🚫 Vacationing in a beautiful villa (think Under the Tuscan Sun) leaving you isolated and missing out on actually experiencing genuine Italian life?

🚫 DIY planning your Italian vacation with TripAdvisor and scoring a deal on Groupon to save big bucks only to find out the activities mentioned were “just suggestions” and “not included in the price” and that you’ve wasted more time planning your vacation than actually vacationing?

🚫 Purchasing a self-guided itinerary, hiring a private driver (white gloves top hat and all), just to realize your itinerary wasn’t put together by locals and those “hidden gems” mentioned are where every other single tour goes?

*Truth Time*

You’ve fallen into just another

tourist trap!

If you’re ready to have that “Wow! I can’t believe this is my life!” Italian moment as you mingle with the locals, indulge in award-winning wines, incredible cuisine, authentic places and exclusive experiences…

…then we’ve got


On this 7 day Italian Adventure

You’ll uncover the nuances of everyday Italian life 

Enjoy the best meal of your life moments

Sit, back & relax by unpacking once at a 4-star boutique hotel just steps away from one of Italy’s most beautiful squares 

And NEVER pull out your wallet for the “extras” not included in the price

You’ll experience the “Real Italy” just like these travelers before you….


“The Italy that so many people who visit Italy multiple times, never get to experience in their lifetime.”


Mooresville, North Carolina, USA


“Giovanni & Chantelle take care of where to go, what to see, where to eat: all while experiencing genuine everyday Italian lifestyle and cuisine.”


San Jose, California, USA


“The exceptional scenery, the out of the way amazing places, wineries and food, all worth the trip to Italy and you wouldn’t find them without Giovanni & Chantelle!”


Melbourne, Australia


“I wanted an authentic experience as a local in Italy. Giovanni & Chantelle absolutely exceeded my expectations!”


Columbia, South Carolina, USA

But first, you need to know

I thought about you during my Big Fat Italian Wedding…

A small town girl from beautiful British Columbia, I knew there was so much more out there to discover and dreamed of traveling Europe. 

On my first trip, I did what most travellers do: big bus tour. Exhausted after returning home and feeling like I barely scratched the surface I knew there had to be a better way to travel.

Then I met Giovanni… 

Determined to find that elusive La Dolce Vita I packed my bags and returned to Italy for the third time. 

But now I had my trusty guide (my future Italian hubby & expert in Italian Food & Wine): Giovanni…

Evening strolls, scenic routes, traveling where the Italians live, digging into authentic Italian food, and discovering all the nuances of everyday Italian life.

This Was The

Italy Insider Difference…

An experience only achievable with a homegrown Italian with passion and expertise for everything Italy. When we finally got around to tying the knot, we wanted to share a slice of our untainted Italy with our bffs…

Which brings me back to my a-ha moment about you…every single guest had their Italy Insider moment.  The kind of experience you can only achieve with local insight and insider intel.

It was that day, walking down the aisle, saying our vows, devoting our love, and sharing our Italy with family and friends…


“I wanted an authentic experience as a local in Italy. Giovanni & Chantelle absolutely exceeded my expectations!”

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

Here’s the thing…


You Only Need to Crave 4 Things to Claim This Exclusive Pass


Meet award-winning winemakers and cook with local chefs in the Italian countryside and still get to toss that coin into the Trevi fountain? Or float away on a romantic gondola ride in Venice? You don’t have to choose. 

Just 3 hours from Rome and a train ride away from Venice you can tag on those bucket-list items before or after your trip with us.


Giovanni’s passion for top quality Italian food and wine is your gateway to local guides, experts, olive oil producers, and drivers (who also happen to be passionate foodies & sommeliers!) leading your entire trip…with a dash of multi-generational wine-makers, & all-star chefs .

We’ve personally tried, tasted and tested every single experience ensuring quality and authenticity. Zero tourist traps, subpar service or food.


Remember that whirlwind Contiki tour you took with 50 other guests? Not your jam anymore. You want to feel like you’re traveling among friends – not a participant on a high school field trip. 

From the moment we welcome you on tour to our final goodbyes, we’ll be there every step of the way…and limit your group to just 12 people. 


 Instead of a whirlwind city-to-city, unpacking and packing every night trip where everything you see and do becomes a blur, you want to create never forget moments with hand-picked highlights connecting you with the locals, fellow travellers, and our beautiful territory of hidden Italy (older than Rome!).  

Join us for just one exclusive date a year!



“This was an experience that throngs of other tourists won’t have. A unique and nice way to see a different culture. And actually spending our last 24 hours in Rome punctuated that. Rome was cool, but we spent exactly the right amount of time there.


North Carolina, USA


“A portion of Italy, we would have never had the luxury of experiencing if we had been traveling on our own.”


San Jose, California, USA

Have we mentioned you can be gourmet gluten-free when you travel with us? 

Your backstage pass to experiencing Italy like a local isn’t off limits because you have to dine gluten-free.

Get a behind-the-scenes look at genuine everyday G-Free Italian lifestyle – at no additional cost to you!

Now you can have your GF cake and eat it, too!


  • 6 nights 4-star boutique accommodations  – including daily spa access – in the historical center just steps away from one of Italy’s most beautiful squares. 
  • 6 breakfasts of local & zero-km products and 7 meals including coffee, dessert, and local wines.
  • Wine experience at boutique family-run Gambero Rosso Award-winning winery
  • All private day trips and guides to some of the Borghi più belli d’Italia (most beautiful medieval villages) throughout Italy’s hidden regions of Le Marche & Abruzzo
  • Bespoke Privately guided walking tour of Ascoli Piceno – a city older than Rome – just for Italian On Tour guests
  • A visit to the Sanctuary of Loreto (one of Italy’s largest Basilicas)
  • Privately guided visit to the Largest Roman Cisterns in Europe & One of the World’s Most Beautiful Libraries
  • A visit to the Adriatic seaside villages on the Coast of Conero
  • All tips for drivers, restaurants and guides included.
  • All entrance fees to monuments included.


  • Private Cooking Experience at a 17th century Villa tucked away in the Italian countryside with a locally renowned chef & level 3 sommelier followed by an organic lunch paired with award-winning wines –designed exclusively for our guests!

  • Private farm and olive grove visit followed by a handmade Chittarra pasta-making demonstration &  farm-to-table lunch with an Italian family paired with award-winning wine selected by a local wine expert  exclusively designed for The Italian On Tour guests!

  • Private Orientation walk of Ascoli Piceno, your homebase on tour, with one of the founders of The Italian On Tour

    And, don’t worry…we’ll pick you up…

    • Pick-up and transfer from Rome’s Fiumicino Airport to Ascoli Piceno.
    • Transfer to Ascoli Piceno’s bus/ train station from the hotel with a private driver. 
    • All ground transportation in private vehicles.

    *Not Included: flights, travel and trip cancellation insurance, items of personal nature, return transfer from Ascoli Piceno to Rome or elsewhere, any items not mentioned in the itinerary.

    YOUR 7-day italy ITINERARY


    Benvenuti!  You’ll be welcomed to Bella Italia by us – Giovanni and Chantelle! 

    Flick your switch to vacation relaxation mode as we whisk you away from Rome’s airport to your boutique hotel located just steps from fabulous shops, charming cafes and one of Italy’s Most Beautiful Squares (and an artisan gelateria, perfect for quenching your daily gelato craving).

    Immediately you’ll sense the rhythm of La Dolce Vita. Unpack once, shake off your jet-lag with a doppio espresso macchiato, and settle into your boutique digs for the week.

    You’ll have ample time to unpack your bags and freshen up. On your trip with us you’ll never feel rushed. This is your Italian vacation and having the perfect balance of free time, interesting towns, people, and activities, is always a guarantee!

    Pre-cena (before dinner), to help you get your bearings, optionally you can meet up with one of the Co-founders of The Italian On Tour, for a private orientation walk of Ascoli Piceno’s charming historic center.

    Need more R&R before dinner? No problem! You can relax at the Spa or simply enjoy some extra time to unwind before dinner.

    Tonight, gather around the dinner table inside a 17th century Villa and get to know your fellow travellers and new Italian bffs. Cin, Cin with a glass of vino rosso, great conversation, and delicious local eats. Round out your first evening with a passeggiata (stroll) in the piazza or hit the sack to catch some Zzz’s before day 2 begins. Buonanotte!


    Meals: Panino Lunch, 4-course Organic Dinner in a 17th Century Villa, including wine & coffee

    Pick-up point: Rome’s Fiumicino Airport at 11:30 am


    Buongiorno! Welcome to your first morning in The Italian On Tour bubble. Everyday begins with breakfast in your charming boutique hotel (want the luxury of breakfast in bed? Room upgrades are available). 

    You’ll always be met at your hotel before embarking on your adventure of the day.

    Connect with a local history expert for your bespoke privately guided walking tour of Ascoli Piceno – exclusively arranged just for The Italian On Tour guests. 

    Energized from your morning espresso, you’ll explore epic millennial history, gorgeous renaissance architecture, dreamy travertine piazzas, Ernest Hemmingway’s favorite cafe, hidden churches, and the historic center of Ascoli that was the movie set of Dustin Hoffman’s Alfredo, Alfredo.

    Worked up an appetite? Next up is a leisurely lunch at a Liberty style Villa followed by a picturesque drive to Italian truffle country.  Stop for a stroll and must-see views of central Italy’s largest mountain range: The Apennines.   

    Post-passeggiata (stroll), and epic panoramic photo ops, you’ll return to Ascoli. Your evening is free to soak up the beauty of the piazza and have dinner on your own (for restaurant recos consult your exclusive The Italian On Tour Dining Guide).

    As in you’ll never have to worry about having a bad meal- with exclusive The Italian On Tour restaurant recos found inside the Vacation Vault, you’ll have a variety of delicious options just walking distance from your hotel.

    Meals: Breakfast, Multi-course lunch including wine & coffee

    Activity: In the morning 2-3 hours urban walking on flat terrain. Easy afternoon stroll and light inclined walking (2-3 minutes of incline)


    Wake up and ease into your day with a creamy cappuccino and get ready to soak up the beauty of Italy’s most underrated coastline & One of Italy’s Most Beautiful Medieval Villages overlooking the Adriatic Sea.

    You’ll travel along the Adriatic seaside to reach the Coast of Conero, a national park, dotted with white sand beaches, marked by the magnificent Monte Conero (Conero Mountain), and lined with endless turquoise waters. 

    Post-passeggiata (walk) of the local seaside villages, it’s time for a 3-course seafood lunch inside an ancient military fortress with the most stratospheric views on this side of the Adriatic Coast.  This is postcard-picture-perfect pristine coastline at its best!

    Next stop is Loreto, world-renowned pilgrimage site and home to a stunning renaissance basilica. Return to Ascoli in the late afternoon for some shopping at the local boutiques or chilling in the piazza. 

    Your trip to Italy wouldn’t be complete without indulging in a gourmet pizza pie! Consult your exclusive The Italian On Tour Dining Guide and wind up your evening with dinner at one of Ascoli’s multiple Gambero Rosso award-winning pizzerias located walking distance from your hotel.


    Meals: Breakfast, 3-course Seafood Lunch paired with wine – designed just for The Italian On Tour guests

    Activity: 2 hours leisurely sightseeing by foot of Le Marche’s seaside villages on the Adriatic coast. Afternoon stroll to visit the town and Basilica of Loreto.

    DAY 4: Cook Cucina Italiana (Italian Cooking) with a local chef

    Enjoy a later start to your day with a leisurely breakfast or take in some solo-exploration.

    Early risers can head to the local farmer’s market to discover seasonal ingredients and partake in a slice of everyday Italian life or check out the latest Italian fashion at the market stalls.

    Mid-morning, be welcomed into the home of a locally renowned chef (featured in La Cucina Italiana) with a gorgeous spread of homemade organic pastries and savory bites, before readying yourself to discover the secrets to Italian cooking inside an authentic frescoed villa typical of Le Marche.

    You’ll get the best taste of local cuisine with your exclusively curated cooking class where you’ll learn how to make one of Ascoli’s signature dishes, followed by a beautiful organic tasting menu of traditional Marchigiani fare.

    After cooking up a storm, you can return to your hotel or optionally you can meet up with Chantelle or Giovanni to visit our favorite place for locally made leather goods, handmade ceramics & the best shop in town to get gourmet goodies to bring back home.

    Your evening is free.

    Now that you’re feeling full-on Italiana head out to the piazza for the local evening ritual of Apericena (Italian style tapas) and a post-gelato passeggiata (stroll).


    Meals: Breakfast, Mid-morning Snack at the Villa before you cooking class, Multi-course organic Lunch (please note that menu varies with the season to offer you the freshest and most flavorful local dishes)

    Activity: 12 hours standing on your feet in the morning while you prepare a meal with a local chef (can’t stand the whole time, no worries, pull up a chair and relax, this is your vacation after all!)


    Today’s adventure will take you underground, beneath the ancient Roman city of Fermo.  

    Step inside an amazing architectural feat – the largest roman cisterns in all of Europe! 

    Then onward to visit a 16th century palazzo which houses important paintings from Venetian & Le Marche school, including a Rubens, and the ancient Globe Room (considered by National Geographic One of the World’s Most Beautiful Libraries) which contains books from the days of Alchemy.

    Pre-pranzo (before lunch) make your way deeper into Le Marche’s hinterlands to continue your journey through Roman history with a visit to a unique locally-owned and operated winery that has its history rooted in Roman military conquests. 

    Your heart will be conquered by the award winning wines, top olive oil and 360 degree hills so stunning they’ve even named two of their wines after it!  

    This 100 acres estate produces Pinot Nero, Syrah, Montepulciano, Lacrima, Pecorino, Sauvignon, Passerina and Chardonnay grapes, in addition to a variety of fruit trees including olives.

    Kick off your 3-course farm-to-table menu and guided wine pairing curated just for The Italian On Tour guests, with an olive oil taste.  

    Post-pranzo you’ll get to enjoy a guided visit on wheels of the entire 50 hectare estate and snap up panoramic views of Le Marche’s hills that expand all the way to the Adriatic Sea. 

    Next up is a private tour of the Wine Cellar and Gambero-Rosso award-winning wine production – exclusively for The Italian On Tour guests. 

    Optionally, before returning to Ascoli you’ll have time to grab a few bottles of wine and olive oil to bring back home and/or put in an order if you’re looking to purchase a few cases.

    The evening is yours to relax, indulge in the rhythm of Italian life, and have dinner on your own. 

    Meals: Breakfast, 3-course farm-to-table menu and guided wine pairing including coffee, water, bread and a tasting of award-winning olive oil

    Activity: A short walk in the morning to visit the city centre of Fermo and its Roman cisterns and the ancient globe room. A visit to the cellar, relaxing on the vineyard’s terrace, and a guided tour of the estate (don’t worry you won’t’ have to walk the entire 100 acres, you’ll get a private visit via golf cart)


    Get ready for another beautiful day in the Italian countryside — and another exclusive Italian On Tour experience.

    Head south to one of Italy’s largest olive oil producing regions. Upon arrival you’ll be welcomed by a family of local farmers that has been working the same land since 1824.  

    Before lunch, you’ll visit the working farm to see where all the seasonal produce, from the olive oil to the zesty sugo al pomodoro (tomato sauce), is grown and made by La Famiglia (the family). 

    Get a taste for true Italian southern hospitality as you’re invited into their family home to gather around the table for lunch. Cooking and eating among four generations you’ll get a taste of what it is like to have your own Famiglia Italiana (Italian Family). 

    Grateful for this once-in-a-lifetime experience, with your heart and belly full, say your goodbyes and jet back to your homebase in Ascoli.  Rest of your evening is free.


    Meals: Breakfast, Multi-course authentic farm-to-table zero-km lunch paired with wine at a multi-generational family-run farm in Abruzzo’s Olive oil country

    Activity: A visit to the farm to learn about the local seasonal produce and how olive oil is made. This is a relaxing day, as if you were spending a Sunday with your very own Italian family.


    It’s check out day…

    You feel elated and invigorated after your trip with us, you’re having this was the “best trip ever” moment. 

    Should you wish to stay longer in Ascoli or explore Rome, Florence, Venice or connect with the ferry over to Croatia, we’ll be happy to offer you local insider advice on how to get to your next destination. 

    Have some time to burn before embarking on the next leg of your journey?  Head to Ascoli’s Saturday Farmer’s Market, open from 9 -12pm.

    You’ll be driven to Ascoli’s bus or train station to connect to the next leg of your trip. 

    Bid farewell, with a hug and a kiss on each cheek (because after your trip with us you’ll be feeling like an Italian now).  

    Until next time “Arrivederci”! Buon viaggio!

    Meals: Breakfast

    Drop-off: Ascoli Piceno bus/train station. Drop-off available between 8:30 to 12 pm

    “Best trip ever! The itinerary was spot on.”

    “Enough free time, interesting towns, great food and wine. Don’t just consider this tour – it is a must.”


    Bethseda, Washtington, DC, USA

    DON’T FORGET Your Trip Perks


    Get the details on catching your flight home or connecting to the next leg of your Italian adventure. We’ll get your flight and connecting destination info to give you personalized trip planning advice.


    Couldn’t quite fork out the coin for the that luxe Michael Kors bag that you’ve been drooling over for months?  Chantelle will take you to a local hidden gem and spot to pick-up your quality Italian leather lookalikes for a fraction of the cost. 

    Psst…more foodie than fashion lover?  Giovanni has you covered.  Head over to Armando’s (no, that’s not the name of the shop!) to taste hand cut prosciutto and stock up on Italian goodies for your trip back home.


    Whether you want to spend the evening sipping aperol spritz in the piazza or hit-up the local art scene, you’ll get our local expert advice for where to eat, what to see, and what’s happening in town.  

    “When I lost my luggage, Giovanni took his personal time to help me sort things out”

    “This showed me that Giovanni & Chantelle really care about their clients. They really went above and beyond the scope of the tour.


    Squamish, BC, Canada

    “Loved the personal shopping tips!”

    “…and all the food recommendations. Giovanni and Chantelle helped us with buying cheese so we could

    bring some of the experience back with us. “


    Brisbane, Australia


    ✔Packing lists & tips

    ✔What you need to know guides

    ✔Restaurant Recos & a local event listing – so you can make the most of your free time on tour!

    ✔Allergy dining out cards for those who are gluten-free (separate cards for celiacs and gluten intolerant)

    “This is where Giovanni and Chantelle live. They have relationships with the people…every experience is very genuine!”

    This is relaxed touring with a personalised touch where you meet the winemakers or producers…It goes beyond herding people in the hopes they’ll buy merchandise. “


    Brisbane, Australia

    Ready to SIP aperol spritz in the piazza?

    starting at 

    $4,997 USD per person

    Grab your spot for just $549 down

     (pop open the prosecco & get excited for your trip)

    “Take the Plunge!”

    The Italian On Tour® is definitely worth the price!

    Relaxing & hassle free, it was the trip of our lifetimes. After the trip we felt invigorated! Wonderful tour hosts, Giovanni & Chantelle, provide unique experiences that you’d never be able to arrange on your own.

    Larry Cooke

    Charlotte, NC, USA


    (and the ones we get asked alot)

    food and wine tours in italy the italian on tour

    1. Who will I be traveling with?

    Giovanni –  Your Exclusive The Italian On Tour host & Italian Food & Wine expert – Chantelle, and your fellow Italian adventurers. Our guests range in age from their 30s to being in their 70s. When you’re on tour with us, age is just a number because everyone is here to sit back, relax, and experience Italy like a local all while enjoying Italy’s amazing culinary and cultural delights.

    italy tours the italian on tour
    “Giovanni & Chantelle are the perfect balance of tour guides & friends.”

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

    Rachel Ruvo

    North Carolina, USA

    “By the second day we were all “family”

    “Giovanni and Chantelle were awesome.

    We had the time of our lives!”


    Michigan, USA


    “With Giovanni & Chantelle’s local knowledge we were able to experience food and restaurants we would’ve never discovered on our own.”


    Squamish, BC, Canada

    2. I’ve already been to Italy...is this the right trip for me?

    Yes, because this means you already love Italy and you’ve probably already traveled to all of Italy’s major tourist sites, but are dying to experience Italy like a local. When you travel with us you’ll experience a new culture among locals who become friends (and know Italy like the back of their hand!). Your trip will be the perfect balance of vacationing and relaxing so you can indulge in La Dolce Vita.

    “You’ll want to go back & experience their Italy, again and again!”


    Toronto, Canada


    As seasoned travelers, we have high expectations. It’s hard to imagine any other place in Italy that better exemplifies the charms of the country that make it a magnet for travellers. It’s even harder to imagine more engaging, charming and thoughtful guides than Chantelle and Giovanni.


    Toronto, Canada

    3. How about if it’s my first time to Italy - don’t I need to go to the Vatican?

    Just 3 hours from Rome and a train ride away from Venice you can tag on those bucket-list items before or after your trip with us.

    While you’re with us, forget worrying about the language, logistics, or having a bad meal – you’ll travel stress-free knowing we’ve taken the guesswork out of planning your trip. 


    This itinerary has been crafted to ensure you’ll enjoy the best of Italy’s hidden regions.  To offer you the best experience possible this trip has limited to just 4 dates. 

    Looking to visit in November? Check out the Italian Truffle Adventure!

    “It was the best trip ever. The tour of a lifetime!”

    We had taken other tours around the world, but this was our first time to Italy. I was a little skeptical at first, not knowing the region of Le Marche, but to my amazement it turned out to be the best tour we have ever done!  If you’re planning on going to Italy choose The Italian On Tour.  After your trip with Giovanni and Chantelle

    you’ll want to go back to experience their Italy again and again!


    Toronto, Canada

    Our accommodation was perfect in quality and location. The hotel staff were very obliging and nothing was too much trouble for them.


    Melbourne, Australia

    5. Where will I be staying?

    Smack dab in the middle of Ascoli Piceno’s historic centre is your homebase. Locally owned and operated boutique 4-star hotel where you can enjoy extra R&R at the spa after a fulfilling day of visiting vineyards & villages.

    Home to one of Italy’s most beautiful squares, you’ll be walking distance to boutique shops, your perfect scoop of gelato, and streets lined with cafes that have something perfect for everyone’s taste buds.

    The hotel was perfect! Clean, friendly staff, great food and my room was very comfortable with lots of space for luggage.”


    Squamish, BC, Canada

    6. I’m not a “tour person” (I usually plan my own trips). Is this right for me?

    Great! Our guests travel with us because they’re looking for an authentic experience, something that they simply cannot pull-off on their own. Think of this as the kind of trip planned by your local Italian BFFs who just happen to be Italian food & wine experts. 

    “It was a nice balance between feeling like we were vacationing and relaxing but also getting the history and learning about the local culture.” 


    North Carolina, USA

    7. Help! I can’t eat gluten?

    No problem! Your backstage pass to experiencing Italy like a local isn’t off limits because you have to dine gluten-free. 

    Get a behind-the-scenes look at genuine everyday G-Free Italian lifestyle – at no extra cost to you!

    Click here to discover how you can travel gluten-free.


    You’ll be picked up from Rome’s Fiumicino Airport at 11:30 am. Flying into another airport in Italy? The Italian On Tour team will help you plan the best way to meet up with your tour.


    Forget the headache of organizing an airport transfer you’ll meet us at Rome’s Fiumicino airport, hop in your private air conditioned vehicle, sit back, relax, and enjoy the ride knowing you’ll be taken care of.

    10. I’m traveling on my own, is it safe?

    Every single city that our tours are based in are selected for their ease of travel and comfortability to be able to walk freely in the evenings and enjoy the amenities of the town you are staying in. Chantelle as an expat and female traveller enjoy walks in the city during the day and evenings. Plus to help you get your bearing for where everything is in town you get an orientation walk on your first night on tour!

    Didn’t find the answer to your question?

    Or maybe you need help deciding which Italy tour is right for you?

    “It was my first time traveling solo and Giovanni & Chantelle made me feel comfortable and very welcome”

    “Ascoli Piceno is a great base for the tour and as a solo traveller I felt very safe there!”


    Brisbane, Australia

    You answered my questions.

    Italy here I come!

    starting at 

    $4,997 USD per person

    Grab your spot for just $549 down

     (pop open the prosecco & get excited for your trip)

    “It's an experience of a lifetime that is worth every dime!”

    "An immersive experience of Italian Culture, Food & Wine. The best part is that while on tour it feels like you're traveling with good friends."


    Santa Clara, California, USA

    We Get It…Life Happens Guarantee


    (minus the $549 non-refundable deposit)

    Take advantage of this guarantee anytime between the day you book your trip and 150 days before your tour departs.  

    Plus your spot is fully-transferable up to 30 days before your tour departs – just in case you wanna score brownie points with your bff.

    Can’t make it on your original departure date?  No problem! 

    You get one complimentary trip switch that you can use to switch your trip to any of the 2024 dates available for your original itinerary up to 60 days before your tour departs.*

    [*Trip switches are subject to availability. For any other cancellations or rescheduling outside the above policy please refer to the terms and conditions for a complete breakdown.]

    “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 steps in.”

    To get the most out of this Italian adventure, you should…

    Be ready for insider knowledge — you already know the best way to experience a new culture is among locals who become friends (and know Italy like the back of their hand!)

    Want to take the guesswork out of planning your trip. Sit back and relax knowing we’ve taken care of it.  

    Never want to feel rushed. You’re in Italy to soak up the local culture and sticking to a by the minute military schedule is NOT your idea of  vacation.  

    Love Italian food, enjoy walking, picturesque countryside, and off-the-beaten-path places where you can immerse yourself in the local culture – you want a ticket to being Italian for a week.  

    …and never want to stress about all the logistics, having a bad meal, or worry about speaking the local lingo.  

    This means, you shouldn’t pop the prosecco if…

    The flow of Italian lifestyle – dinner at 8pm, shops close for siesta-leisurely meals, and a full glass of vino – isn’t your jam. 

    Exploring picturesque villages by foot doesn’t feel fun. We visit hill-top villages— exploring them means we’ve arranged some private walking tours to give you insight into the history and local culture.

    (Please refer to each individual day in the itinerary for an approximation of the activity level.)

    You’re a picky eater.  Getting to know the local culture means trying a variety of authentic dishes – your meals on tour run the gamet of everything from organic cheeses, seafood and meat.

    Boutique 4-star accommodations with focus on location to amenities, relaxation, character and pure Italian charm isn’t where you want to stay. You’re looking for huge rooms, a swimming pool & accommodations located far outside the city center. (Need extra space? Want to enjoy an evening at the spa? Don’t worry! Upgrades including full access to the spa & breakfast in your room are available)

    “You’re not shuffled in and out of a bus. There are no lines to cue up in. Chantelle & Giovanni take all the guesswork out of planning your Italian vacation.”


    “They take care of where to go, what to see, where to eat: all while experiencing genuine everyday Italian lifestyle and cuisine.  The authentic Italian food was AMAZING! And best of all we had two locals to enlighten each day with their knowledge and experiences.”


    San Jose, California, USA

    Still Reading?

    Then You Should Know This…


    Plenty of people will DIY it and book that too-good-to-be-true big bus tour because they think they’ve gotta see Italy’s famous spots or that they’ve scored a deal of a lifetime.

    And here’s what will happen…

    They’ll wind up being just another tourist on a big bus tour with 50 other people or stranded in the Italian countryside without a clue of where to go, what to see, who to meet, and what to eat.

    …leaving you on the sidelines, missing out on experiencing the real Italy.

    But that isn’t going to be you…

    You want more time relaxing than spending countless hours planning and stressing about all the details

    You want to forget about getting from point A to B, and relax knowing you’ll be taken care of

    You want to enjoy sipping vino rosso under the Italian sun, digging into that second plate of pasta all’uovo made with Nonna’s love, and treating yourself with a second scoop of gelato because you’re in Italy and everyday is a celebration.

    “It was a life-changing trip!”

    What an amazing experience! This was my mom’s first trip to Europe and she can’t stop talking about it.

    Chantelle and Giovanni introduced us to an abundance of upscale, indulgent, fresh Italian food every single day.

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


    Seneca Falls, NY, USA

    READY for a life-changing italy trip?

    starting at

    $4,997 USD per person

    Grab your spot for just $549 down

     (pop open the prosecco & get excited for your trip)

    “They should charge more!”

    Their prices are unbelievably fair. If you’re hesitant about their pricing then I would say don’t go to Italy…”


    North Carolina, USA

    New York Times Bestselling Cookbook Author, and Creator of Nom Nom Paleo



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