For Food & Wine Lovers that want to visit italy without the crowds, UNWIND In WINE COUNTRY & eat your way through the hidden gems of Le marche & umbria  like a local

As seen in:



the italian on tour

Leave the Umbrella Waving Tour Guide (+ Crowded Bus) Behind, Immerse yourself in the Green Heart of Italy, Visit the Birthplace of Raphael, Travel to verdant vineyards that produce World-class Wines & enjoy Incredible Italian Food with…


…and explore Italy’s undiscovered corners of Umbria & Le Marche like a local on this 10-day all-inclusive adventure.

For 9 nights, indulge in personalized service, authentic cuisine and real Italian life.  

Plus, exclusively curated experiences & bespoke day trips (including some of Italy’s most beautiful villages, majestic natural history, biodynamic food producers & award-winning 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 meeting the locals & 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 (like Gambero Rosso award-winning chefs & local sustainable farmers), indulge in top Italian wines, incredible meals, authentic places and exclusive experiences…

…then we’ve got


On this 10 day Food & Wine lovers Journey based in Umbria

You’ll uncover the nuances of everyday Italian life 

Enjoy the best meal of your life moments

Sit, back & relax by unpacking once at One of the Small Luxury Hotels of the World

Just minutes from wine country & where scenes from the original Rome & Juliette were filmed.

And NEVER pull out your wallet for the “extra” activities or get dinged hundreds of dollars in “booking fees” 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, eat zero-km organic authentic Italian cuisine inside an ancient abbey from the year 1000, relax at your 4-star luxury stay with spa 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 & Chantelle’s passion for top quality Italian food and wine is your gateway to local guides, experts, celebrity chef approved honey 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 (that become family) – 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 that is home to Verdicchio wine, the largest underground cave system in Europe, the Birthplace of Raphael, UNESCO heritage, and ethical farmers raising animals as nature intended.  

use the calendar to select from the following available dates:



September 1 to 10, 2024 – just 1 spot left!


September 28 to October 7, 2025

choose from the following available dates:



September 1 to 10, 2024 – just 1 spot left!



September 28 to October 7, 2025


“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

SNEAK PEEK INTO YOUR 10-DAY all-inclusive italian vacation

  • 9 nights boutique 4 star accommodations with a  swimming pool, gym & spa amenities* –  in the Green Heart of Italy
  • All Meals as per the itineraryread each day of the itinerary for a description of each
  • Discover authentic beyond-organic Italian cuisine with an exclusively curated meal dining inside an ancient abbey 
  • Learn about the local cuisine with two organic farm visits.
  • Taste Wine like a local with 3 Winery experiences at Award-winning wineries  in Umbria & Le Marche – plus a wine taste at a regional Enoteca.
  • Privately guided visit to the Largest Underground Karst Cave System in Europe
  • A Privately Guided Walking tour of Gubbio – just for The Italian On Tour® guests
  • 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 & Umbria
  • Privately guided walking tour of Matelica – the City of Verdicchio di Matelica – just for The Italian On Tour® guests
  • Bespoke Privately guided walking tour of Urbino – World UNESCO heritage site home to the most well preserved Renaissance Palace – just for The Italian On Tour® guests 
  • Guided visit of Fabriano, the Unesco City of Creativity, paper-making history where you’ll meet Master artisan papermakers & get a demonstration of traditional paper making
  • All tips for drivers, restaurants and guides included.
  • All entrance fees to monuments included.


  • Private Honey-making experience  with a nationally renowned beekeeper (whose honey is featured on  Michelin-starred menus) &  followed by a visit to an organic farm that has been sustainably raising life-stock and producing organic cheese for over 30 years – designed exclusively for our guests! Followed by enjoy lunch inside an ancient abbey paired with local wines  followed by a visit to their cheese production. 

  • Meet Le Marche’s Top Wine Producer to learn about the latest innovations in wine production,  and dine  on a Curated tasting menu overlooking the hills of Castelli di Jesi! 

  • Welcome Wine Tasting Evening  in Umbrian Wine Countryjust for The Italian On Tour® Guests – with your tour hosts, Giovanni & Chantelle, 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 your accommodations.
  • Drop-off and transfer to Fabriano 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 Fabriano to Rome or elsewhere, Spa entrance/spa services, and any items not mentioned in the itinerary.

YOUR All-inclusive 10-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 accommodations near  the Le Marche-Umbria border. A 17th century monastery masterfully converted to one of the Small Luxury Boutique Hotels of the World.

You’ll be on the near by hills, just a 15 minute walk to one of Italy’s Most Romantic cities where the original Romeo and Juliet was filmed. and enjoy amenities that include a gym, full service spa and a swimming pool. The easy access to the center and historic ambience of this place makes it perfect for your free evenings out explore or staying in and relaxing with a delicious dinner and glass of wine at your luxury historic stay.

Immediately you’ll sense the tranquility of this ancient monastery, setting the stage for a vacation of complete relaxation. Unpack once, and settle into your room. We’ll arrive late afternoon with plenty of time to freshen up and kick off your Italian vacation with a dip in the pool.

Tonight, gather around the dinner table at a local winery that got its start by producing Nebbiolo di Gubbio – which is made from Dolcetto grapes. They currently make IGT wines using the red grapes of Dolcetto, Merlot, Pinot Noir, Cabernet Sauvignon and the wine grapes of Chardonnay, and Petit Verdot.

It’s time to get to know your fellow travelers and new Italian bffs as you Cin, Cin with a glass of the local vino, great conversation, and delicious local eats paired with wine. 

Besides your first night on tour, every night your dinner will be at your hotel and it includes 3-courses and a glass of wine, so that on your free time in the evening you’ll have the freedom to explore their extensive wine list should you want additional vino.

Round out your first evening by relaxing by the fire or hit the sack to catch some Zzz’s before day 2 begins. Buonanotte!

Meals: Panino Lunch, Welcome Winery Dinner paired with wines.

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 at your hotel.

You’ll always be picked up directly from your accommodations before embarking on your adventure of the day.

Just minutes from your homebase on tour is Gubbio: One of Umbria’s Most Ancient Cities.

Once a powerful medieval city state, thanks to its thriving industry of majolica pottery, Gubbio’s architectural masterpieces showcase its heyday.

Nowadays, its modern claim to fame is the World’s largest Christmas tree made of lights that it displays proudly each year on the slope of Monte Ingino and for it’s medieval center that was featured in the original filming of Romeo and Juliet.

After uncovering the hidden gems of Gubbio’s ancient historic center, you’ll head deeper into Umbria’s countryside to lunch to enjoy seasonal local dishes typical of the area paired with wine.

Post-pranzo, you’ll enjoy a guided visit to the cellar before returning to the comfort of your 4-star luxury stay and take in the scenery as you travel back through the Umbrian countryside.

The evening is yours to relax, indulge in the tranquility of wine country, soak up the scenery at the spa/pool and enjoy dinner at your hotel.

As in you’ll never have to worry about where to look for your next meal- everything is taken care of for you on this all-inclusive Italian vacation.


Meals: Breakfast, Lunch, Dinner. 

Activity: Walking tour of varied terrain of the hillside town of Gubbio. Lunch followed by a visit to the cellar and the estate.


Today’s adventure will take you over the border to the Verdicchio di Matelica wine country to visit Matelica a city in the Le Marche region.

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

Energized from your morning espresso, you’ll uncover the history that you can’t find in guidebooks and learn about the silk makers, gorgeous Renaissance architecture of the local theater, and the Ancient Roman ruins hidden beneath the city.

Before making your way to lunch, it’s time for another event arranged just for The Italian On Tour® guests. A visit to the hometown of Verdicchio di Matelica wouldn’t be complete without a wine taste at the regional Enoteca. 

Post-wine tasting, it’s time to re-energize with a leisurely lunch followed by some afternoon sightseeing

Late afternoon/early evening you’ll return to your accommodations with time before dinner to do as your heart desires. Go for a walk into Gubbio’s historic center, enjoy a dip in the pool, soak in the scenery from the comfort of the spa’s rooftop jacuzzi or book yourself a massage to completely unwind before dinner.

This is your vacation after all and it’s our aim to ensure you enjoy the perfect balance of free time & scheduled activities.

Meals: Breakfast, Wine Taste, Lunch, Dinner 

Activity: In the morning 2-3 hours urban walking on flat terrain. Cobblestones and a mix of inclined walking. Too much walking for one day?  You’re free to stop at a cafe (don’t worry we’ll come get you before we leave!) or take the whole day off relaxing at the estate – it’s your vacation after all!


Yesterday, your senses were inspired by history and Umbrian wine. Today your tastebuds will be enlightened by nature with a private visit to a local organic biodynamic honeymaker producing what many consider the best honey in the entire country (including Michelin-starred chefs, like Heinz Beck, that feature it on their menus). This is a once-in-a-lifetime opportunity to discover how truly sustainable honey is produced and taste the difference for yourself.

Post-honey tasting you’ll continue your journey through ethical food production with lunch followed by a visit to an ancient abbey which houses an organic farm.  A farm that honors the passion of the women and men who have managed the Abbey since 1005 by raising their livestock as nature intended: wild & free to roam.

The true definition of happy cows & hogs – their animals enjoy their days on entirely organically cultivated pastures upon the hills overlooking the Esino Valley. 

A stunning valley, where your accommodations are situated, and is currently in the approval process of becoming a UNESCO heritage site (as in a real upcoming spot, that you’ll want to visit while its hidden gem status is still in full effect).

After a day of tasting the gifts of nature’s excellence, you’ll be whisked back to the tenuta (estate) to enjoy some free time to your heart’s content, and have dinner at the estate with your new found friends.

Meals: Breakfast, Multi-course organic lunch with wine, coffee and dessert, Dinner at the estate.

Activity: Relaxing morning of a visit to a honey producer and organic farm that you get to enjoy the products at lunch including pork, beef, and a variety of local cheeses.  Tour of the farm. Evening at the tenuta to enjoy the luxe amenities and have dinner as you please.


Head North to the province of Ancona for a privately guided visit of the Frasassi Caves, the Largest Underground Karst Cave Complex in all of Europe! 

Equipped with walkways & lighting, you’ll be able to access 1.5 km of this crystalline wonderland of stalagmites and stalactites, and the Grotta Grande del Vento, Europe’s Largest Single Cavern, so vast that the Duomo of Milan can comfortably fit inside it!

Inspired by nature’s epic creations, you’ll continue on a journey for the senses at a family-run Slow Food Trattoria that creates authentic dishes in full respect of the land and the local traditional recipes.

Post-wining and dining, enjoy some afternoon sightseeing to Sassoferrato one of Italy’s Borghi più belli d’Italia (Most Beautiful Medieval Villages),  before returning to your home base in the heart of Verdicchio di Matelica wine country.

Your evening is free to enjoy another Bella serata (beautiful evening) filled with R&R and dinner at the estate.

Feeling like you need to give your legs a spin? The estate is equipped with bikes that you can rent for some solo exploration of the pristine countryside.

Meals: Breakfast, Multi-course lunch with wine, coffee and dessert, Dinner

Activity: In the morning 2-3 hours walking on varied terrain, sturdy shoes recommended as the ground can be wet inside the caves.  Afternoon sightseeing, leisurely stroll.


To complement the decadent meals, stunning natural history & fabulous wines, today you’ll be introduced to the art of handmade paper making with a visit to the UNESCO City of Creativity: Fabriano. Fabriano got its claim to fame as one of the earliest places of paper production in Europe. With over 700 years of local papermaking tradition, the city is still renowned today for its fine watermarked paper.

A visit to Fabriano wouldn’t be complete without a live demonstration of hand-made paper making, performed by a Master paper makerjust for The Italian On Tour guests!

Fallen in love with some of the gorgeous paper and notebooks? We’ve got you covered! You’ll have enough time to peruse the handmade paper and stop by for a visit at the Oldest Stationery shop in Fabriano. 

Post-artisan visit & a little optional shopping, it’s about time for another beautiful meal together. Your lunch today is at a modern Osteria  where you’ll get to  treat yourself to a 4-course tasting menu. The cuisine is a flavorful blend of traditional and contemporary with a focus on seasonal ingredients, The perfect compliment to yesterday’s traditional fare.

Buzzing from a morning of culture and amazing food, the rest of the afternoon is yours to indulge as you please.  Perhaps it’s a stroll through the vineyards, a bike ride through wine country, sipping some bubbly poolside, or lounging around with a good book.

Whatever is your jam, you’ll have some free time to take it all in before dinner.

Meals: Breakfast, 4-course tasting menu including wine, coffee and dessert, Dinner at the estate

Activity: In the morning 2-3 hours walking/standing for a walk in the historic center of Fabriano and a visit to the Master papermakers. After lunch you’ll have free time to enjoy the rest of the day as you please.


Wake up and ease into your day with a double cappuccino morning. Early risers can enjoy the serenity of staying at a luxury boutique wine estate with a walk through the vineyards. Or simply savor some free time before you head out to soak up the beauty of Italy’s Verdicchio dei Castelli di Jesi wine country. An area of DOCG wine production known for the Top White Wine in the World made from Verdicchio grapes.

Travel through Le Marche’s hinterland to reach the largest wine cooperative in the entire region that has been producing organic wines since 1980.  Here you’ll enjoy an insightful guided visit of the innovative and sustainable production practices used to make wines from Verdicchio, Montepulciano, Sangiovese, Pecorino, Lacrima, Passerina, Trebbiano, Merlot, Pinot Noir, and Chardonnay.

Vineyards that set the mood for a seafood lunch after a visit to the cellar that produces all the bubbly in house (unlike most wineries outside of the Prosecco hills that send their grapes up to Veneto) using the Classic method in which every single bottle is hand-turned,

You’ll be dining on a bespoke menu (designed just for The Italian On Tour® guests) at a restaurant run by a lovely husband-wife team that is housed in a beautifully restored country home located above the winery’s cellar.

Post-pranzo, take the scenic route back to the tenuta. The rest of your evening is free to have dinner on your own and enjoy some R&R.

Meals: Breakfast, Lunch, Dinner

Activity: Morning visit of the winery, the production facility, and cellar, followed by lunch overlooking Verdicchio dei Castelli di Jesi wine country. Afternoon sightseeing and photo-stop.


Today’s adventure take you east into the hinterland of the Duke of Montefeltro where you’ll discover Urbino, the Birthplace and hometown of Raphael, the Renaissance painter, considered more versatile than Michelangelo and more prolific than Leonardo, with a privately guided walking tour – just for The Italian On Tour® guests.

You’ll get to know the UNESCO heritage of Urbino’s historic center and be awestruck by it’s stunning renaissance architecture said to be one of the most important places during the Italian Renaissance, whose architectural heritage is still fully preserved today. Understanding how Urbino’s people and history shaped Italy’s Renaissance is essential to understanding the local culture and why this is a must visit on your trip.

After working up an appetite, up next is a trip to a Slow Food Agriturismo in Le Marche’s countryside to enoy a rustic lunch of traditional specialities.

Feeling satified after the perfect morning and afternoon of relaxing and planned activities, you’re ready to return to your homebase and soak it all in, rounding out your evening dining in style at your hotel or you can head into Gubbio’s historic center for a night on the town as you’re just a 15 minute-walk from the center.

Meals: Breakfast, Lunch, Dinner 

Activity:  Early-morning head east for a Privately Guided Walking tour of Urbino, 3 hours on your feet, and then relax for a leisurely Sunday lunch in Le Marche’s countryside.


Wake up to another day in Bella Umbria! Take in the sounds of the birds and before heading to an organic farm at the foothills of Monte Cucco.

Not only organic, but this 150 hectare estate uses photovoltaic energy and committed to being greener everyday. When it comes to sustainbility, they don’t just talk the talk, they walk the walk.

Of course no first to a local farm would be complete without tasting the traditional specialities! Post-guided farm-visit we’ll gather round the table to lunch inside the restored ancient farm hourse.

During the drive back to your, you’ll be buzzing from the beautiful sites, sounds, flavors, and feeling grateful for the local connections you made because by now you’re feeling like la famiglia (family)

You’ll have time to pack your bags and enjoy dinner your hotel. 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!

Embracing the Italian art of “Dolce far niente” (the sweetness of doing nothing),  spend your last evening on your trip with getting in one last dip in the pool.


Meals: Breakfast, Lunch, Dinner 

Activity: Morning guided visit of a local farm followed by lunch, afternoon sightseeing, return to your hotel


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 Matelica 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. 

You’ll be driven to Fabriano’s 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: Pick-up at 9 am from your accommodations to make departures leaving after 10 am from Fabriano’s Train station.

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

“Enough free time, interesting towns, great food and wine. Don’t just consider traveling with The Italian On 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.


From Artisan made paper to visiting wine cellars displaying art, we’ll take you to the best local spots to get unique gifts to bring back home.

Psst…more food & wine lover than artisan addict?

We’ll take you to an organic honey producer, and multiple award-winning wineries where you can taste, try & purchase your favorites to take back home.


Whether you want to spend the evening hitting-up the spa, staying in with a good book or taking an evening jaunt to the historic center, you’ll never have to worry where to get your next meal!  Every evening a 3-course dinner is included at your hotel.

“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 before you go guides

✔Detailed photos & directions for where to meet up with your tour –  so you don’t have to stress about if you’re in the right location or not!

✔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 vino by the vineyard?

starting at 

$7,997 USD per person

Grab your spot for just $997 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 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 1 dates in September.

September is the month of the wine harvest & it’s the perfect weather for enjoying the evening dining al fresco, and  exploring Umbria’s undiscovered treasures.

“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

10 day food and wine tour umbria italy

5. Where will I be staying?

Smack dab in the middle of the Green Heart of Italy is your homebase at the Park Hotel Ai Cappuccini. A beautifully restored Monastery from the 1600’s converted into One of the Small Luxury Boutique Hotels of the World. Locally owned here you can dine in style, take a dip in the pool and enjoy extra R&R with a full service spa after a fulfilling day of visiting villages, epic natural sites, local artisans, world-class winemakers & organic food producers.

Unbeatable for its proximity to the center, it’s the perfect setting to completely unwind on your Italian vacation, while providing you with all the amenities & tranquility to perfect the Italian art of “Dolce far Niente”.

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 bespoke 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?

Your backstage pass to Italy isn’t off limits because you have to dine gluten-free.  Although the Italy Uncorked is NOT available gluten-free you can still get a behind-the-scenes look at genuine everyday G-Free Italian lifestyle – at no extra cost to you – when you join any of tours that can accommodate gluten-free travellers.

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 solo, 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.

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”

“As a solo traveller I felt very safe!”


Brisbane, Australia

You answered my questions.

Italy here I come!

starting at 

$7,997 USD per person

Grab your spot for just $997 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

pay for your italy trip in 3 just instalments

italian tours

secure your spot

with just $997 USD down per person

  • Pop the Prosecco because when you make down your deposit your pricing is locked-in. 
  • Unlike, many other companies, with us your price never is subject to increases, even if our costs go up.
food tours italy

2nd instalment

$2997 USD per person

  • plus any single supplements or room upgrades
  • Payable by 180 days before your trip’s departure date
  • You’ll get a reminder 5 business days before your next instalment, so you’ll never have to stress about making a late payment
italy tours

last instalment

your remaining balance

  • Payable by 90 days before your trip’s departure date
  • Cin, cin! You’re all set to travel Italy like a local. We can’t wait to meet you in Italy!



as in you pay what you see, no surprises ever!


“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 & taking the stairs is an impossible feat. We visit Europe’s Largest Underground Cave system – seeing it means walking on varied terrain.

(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.

Small Luxury Hotel  steeped in history with focus on spa amenities (including a swimming pool & gym), relaxation, delicious local fare and true Italian hospitality isn’t where you want to stay. You’re looking for accommodations located in the city center. (Need extra space?  There are suites upgrade availabile)

“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

$7,997 USD per person

Grab your spot for just $997 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



Get your Gluten-Free Italy Survival Guide...


The Top 10 Tips To Avoid Vacation Glutenation on Your Trip to Italy

Your Gluten-Free Italy Survival Guide is on its way!

Pin It on Pinterest