TASTE OF ITALY

5 day Italy itinerary for food & wine lovers that want a backstage pass to experiencing Italy like a local

 Leave the Umbrella Waving Tour Guide (+ Crowded Bus) Behind, Sink into 5 days of La Dolce Vita and Take a Bite out of Italian life With…

TASTE OF ITALY

…and explore Italy’s hidden regions like a local.


For 4 nights, indulge in
personalised service, authentic cuisine and real Italian life. 

Plus, exclusively curated day trips (including some of Italy’s most beautiful medieval villages).

“WE GOT TO SEE THE REAL ITALY!”

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

JENNIFER LEVESQUE

Mooresville, North Carolina, USA

“WE WANTED TO BE ITALIAN FOR A WEEK”

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

RACHEL RUVO

North Carolina, USA

Must-Answer Question for Food & Wine lovers 

Ready to Experience Italy Like a Local

What’s the difference between visiting Italy and actually experiencing genuine Italian life and authentic cuisine?

Possible answers…

►  Rolling up in a coach bus packed with 50 people on a whirlwind “Ultimate Italy” tour (because heck you haven’t been to Italy if you didn’t check Rome, Venice & Florence off your bucket-list?!).

►   Slowing down and choosing a beautiful villa (think under the Tuscan Sun kind-of-beautiful) hidden away from it all in the Italian countryside.

►   DIY planning with TripAdvisor and scoring that deal on Groupon to save those big bucks!

►   Purchasing a self-guided itinerary, hiring one of those fancy drivers, white gloves top hat and all, to take you on your   “golden ticket” itinerary.

Sorry. Wrong answers. 

(Yes, even the tour one!)

HERE’S THE THING…

You’re probably thinking booking that “ultimate Italy tour” will check off the sites, but you know you’ll be exhausted from fighting your way in lines, and wasting your precious vacation days on a crowded bus. 

Oh, and nickel and diming your way because the activities mentioned in that Groupon deal were “just suggestions” and “not included in the price.” 

And secretly you know those done-for-you free independent traveller journeys weren’t put together by locals.

Without that insider knowledge it’s hard to have that “Wow! I can’t believe this is my life!” Italian moment…

…even harder to find authentic places for food and wine, and darn near impossible to mingle with the locals.

Which makes planning your trip to Italy trip (you know – the thing you’ve dreamed about checking off your bucket-list since your first slice of pizza napoletana) one big tourist trap! 

Guess what?

That won’t be you…on tour with us!

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): 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 achievableable 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…

YOUR BACKSTAGE PASS TO ITALY WAS BORN.

“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.

STEPHANY BRANHAM

Columbia, South Carolina, USA

Here’s the thing…

 

you only need to crave 4 things from your trip to get this exclusive pass.

★Small Group

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. 

★live la dolce vita full out

Meet award-winning winemakers and cook with locals 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.

★ACCESS TO LOCAL EXPERTS

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

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

★MAKE MEMORIES

 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!).  

“OTHER TOURISTS WILL NEVER HAVE THIS EXPERIENCE!”

“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.

RACHEL RUVO

North Carolina, USA

“SINCE OUR GROUP WAS SMALL WE GAINED INSIGHT & ACTUALLY EXPERIENCED ITALY”

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

ANNETTE PETRO

San Jose, California, USA

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

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

SNEAK PEEK INTO YOUR 5-DAY ITALIAN ADVENTURE

 

  • 4 nights 4-star boutique accommodations in the historical center just steps away from one of Italy’s most beautiful squares. 
  • 4 breakfasts, 5 meals including coffee, dessert, and local wines.
  • All tips for drivers, restaurants, and guides included.
  • Privately guided visit to the Largest Roman Cisterns in Europe
  • All private day trips and guides to some of the Borghi piu belli d’Italia (most beautiful medieval villages) throughout Italy’s hidden region of Le Marche
  • Privately guided walking tour of Ascoli Piceno arranged exclusively just for our guests
  • All optional afternoon sightseeing including a visit to Italy’s Narrowest alleyway (as recorded in the Guinness World Book of Records) and local Truffle Country
  • All entrance fees to monuments included.

PLUS THESE EXCLUSIVE EXPERIENCES…

  • Private Cooking Experience using seasonal local and organic ingredients (designed exclusively for our guests!)
  • Organic and biodynamic wine tasting at a Gambero Rosso award-winning family-run winery (designed exclusively for our guests!)

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, retuurn transfer from Ascoli Piceno to Rome or elsewhere, any items not mentioned in the itinerary.

YOUR 5-day italy ITINERARY

DAY 1: ROME TO HIDDEN ITALY

Benvenuti! You’ll be welcomed to Bella Italia by us – Giovanni and Chantelle! Flick the switch to vacation relaxation mode. 

Be whisked away from Rome’s airport to your boutique hotel, steps from fabulous shops, charming cafes and one of Italy’s most beautiful squares (and an artisan gelateria, perfect for that obligatory daily gelato fix). 

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

Tonight, gather around the dinner table 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 an passeggiata (stroll) in the piazza or hit the sack to catch some Zzz’s before day 2 begins. Buonanotte!

Meals: Lunch, Multi-course Dinner

Pick-up point: Info Point in Terminal 3 located in Rome’s Fiumicino Airport at 11:30 am

DAY 2: THE CITY OF TRAVERTINE, 100 TOWERS & TRUFFLE COUNTRY

Buongiorno! Welcome to your first morning in The Italian On Tour bubble. Everyday begins with breakfast in the elegant courtyard of your boutique hotel. You’ll always be at met at your accommodations before embarking on your adventure of the day.

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

Energized from your morning espresso you’ll explore epic millennial history, gorgeous renaissance architecture, Ernst Hemmingway’s favourite cafe, and hidden churches that’ll make you go “Wow!”.

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

Post-passeggiata (stroll) 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 Vacation Vault for your exclusive Italian On Tour dining guide).

Meals: Breakfast, Multi-course Lunch

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

DAY 3: WINE & ROMAN TIMES

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! 

Continue your journey through Roman history with a visit to a unique family-run organic and biodynamic winery that makes wine the Roman way. David, a sommelier and local winemaker, will welcome you to the cantina for a private tour of the Gambero-rosso award-winning wine production. 

Settle into taste the goods with an exclusive wine tasting paired with local charcuterie and the perfect plate of ragu that’ll make you reach for another splash of vino rosso, or two! 

After lunch, beat your pasta coma with a stroll in Moresco, a quaint hill-top town that is one of Italy’s “Borghi piu belli d’Italia” (most beautiful medieval villages in Italy) before returning to Ascoli.

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

Meals: Breakfast, Multi-course lunch paired with local organic and biodynamic wines

Activity: A short walk in the morning to visit the city centre of Fermo and its Roman cisterns. A visit to the cantina, relaxing on the vineyard’s terrace, and a short afternoon stroll.

DAY 4: Learn the secrets to Cucina Italiana (Italian Cooking)

Wake up and ease into your day with a double cappuccino morning. Head to the local farmer’s market to discover seasonal ingredients and partake in a slice of everyday Italian life or simply enjoy some free time before your cooking experience.

In Italy ingredients change with the season, and so do our chefs.  Depending on the time of year you visit, you’ll discover the secrets to Italian cooking with an Award-winning Master Pizzaiolo (Pizza Maker) or head to the Italian countryside to prepare lunch with a locally renowned chef.

 Be welcomed inside their kitchen for an “The Italian On Tour” exclusive cooking experience. 

Post-cooking, sit down and enjoy the fruits of your labor with a gourmet pizza or a perfect plate of pasta all’uovo that reflects the best of the season.

Late afternoon, join in on some afternoon sightseeing through wine country and squeeze your way through Italy’s Narrowest Alleyway (this one’s in the Guinness world book of records). 

The evening is yours to relax, dig into another plate of handmade pasta, (if you’ve managed to save some room after your cooking experience).

Meals: Breakfast, Lunch (please note that the menu varies with the chef and the season to offer you the freshest and most flavorful local ingredients)

Activity: 12 hours standing on your feet in the morning while you prepare lunch with a local chef (can’t stand the whole time, no worries, pull up a chair and relax, this is your vacation after all!), optional afternoon sightseeing to visit Italy’s Narrowest Alleyway.

DAY 5: ARRIVERDERCI!

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. Be driven to Ascoli’s bus or train station to connect to the next leg of your trip. 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 our local insider advice on how to get to your next destination. 

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 10:30 am

DON’T FORGET Your Trip Perks

★PERSONALIZED SERVICE

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 your personalized trip planning advice.

★INSIDER RECOMMENDATIONS

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.

RACHELLE HYNES

Squamish, BC, Canada

★SHOPPING TIPS

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.

“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. “

ANNA PESTI

Brisbane, Australia

PLUS…A LIFETIME PASS TO THE VACATION  VAULT

✔Packing list

✔What you need to know guides

✔Restaurant recos (all over Italy for your post-trip planning)

✔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. “

BELINDA REILLY

Brisbane, Australia

Ready to be sipping aperol spritz in the piazza?

$2,495 USD per person

Grab your spot for just $495 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…”

RACHEL RUVO

North Carolina, USA

THE 10 QUESTIONS YOU WANT ANSWERED

(and the ones we get asked alot)

1. Who will I be traveling with?

Us! Giovanni and Chantelle and your fellow Italian adventurers. Our guests range in age their late 20s 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.

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.

“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

“I’VE BEEN TO ITALY MULTIPLE TIMES & NO OTHER EXPERIENCE COMPARES.”

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

KELLY SERVINSKI

Squamish, BC, 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. 

4. No dates are available for when I want to travel? What do I do?

We accept departure date requests for a minimum of 6 people. If you know exactly when and what trip you would like to book and are ready to set you dates in stone simply click here to put in your date request. (Please note that date requests are based on availability and are on a first-come, first-serve basis.)

REQUEST DATES ARE NO LONGER BEING ACCEPTED FOR 2020.

“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.”

RACHEL STENDER

Bethseda, Washtington, DC, USA

5. Help! I can’t eat gluten?

No problem! Your backstage pass isn’t off limits because you have to dine gluten-free.  Get a behind-the-scenes look at genuine everyday G-Free Italian lifestyle. Click here to discover how you can travel gluten-free.

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. 

“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!”

LEE FARRINGTON

Melbourne, Australia

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

 

RACHEL RUVO

North Carolina, USA

7. WHICH AIRPORT DO I FLY INTO?

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

8. How do I meet up with my 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.

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

LEE FARRINGTON

Melbourne, Australia

The hotel was perfect! 

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

RACHELLE HYNES

Squamish, BC, Canada

9. 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 famous guests slept (Sting stayed here!) 

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 everyone’s taste buds.

10. I’m traveling on my own, will I be charged a single supplement?

Heck no! You’ll be paired up with another solo traveller. 

Don’t want to share a room? No problem! You can have the privacy of your own room for just $395.

“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!”

BELINDA REILLY

Brisbane, Australia

We Get It…Life Happens Guarantee

 

IF, FOR ANY REASON, YOU CAN’T TRAVEL WITH US, GET YOUR MONEY BACK. 

(minus the $495 non-refundable deposit)

Take advantage of this guarantee anytime between the day you book your trip and 75 days before your tour departs.  

Plus your spot is fully-transferable – just in case you wanna score brownie points with your bff.

Can’t make it this year?  No problem! You can use your $495 non-refundable portion towards any trip booked within one year of the anniversary of your initial booking.

[If you cancel within 74 days of your tour, please refer to our terms and conditions for a complete breakdown.]

You answered my questions. Italy here I come!

$2,495 USD per person

Grab your spot for just $495 down

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

“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.  

➤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 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.)

Boutique 4-star accommodations with focus on location to amenities, character and pure Italian charm isn’t where you want to stay. You’re looking for a spa and swimming pool.

“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.”

ANNE PETRO

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 made with Nonna’s love, and treat yourself with a second scoop of gelato because you’re in Italy and everyday is a celebration.

 

Ready to be sipping aperol spritz in the piazza?

$2,495 USD per person

Grab your spot for just $495 down

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

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

STRESSED ABOUT GETTING GLUTENATED ON YOUR TRIP TO ITALY?

 

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

BOOK NOW