Design Your Trip

Expertly tailored to you!


At “The Italian on Tour” we understand that the best way to experience a new and exciting place is to do so at your own pace. Our tours already offer small group sizes but if you are looking for something more intimate and aligned with your needs, we design personalized tours for a minimum of two guests.



We will take care of every little detail and expertly tailor your tour based on your preferences and budget.

Unlike most customized tours of this kind offered in Italy, you will be accompanied by a Fully-bilingual Guide that was raised in the area, giving you the insider’s scoop to Italy (Want to learn more about your Guide? Click here!).  Our custom tours offer the complete attention of your Guide as well as, exclusive visits to small wine and olive oil producers and cooking classes only available to you.

Our private tours offer a lot of flexibility; you will be free to change your itinerary or leave at a later time for an excursion or an event. You will have the ability to spend a bit of extra time at a castle or take more pictures of the surrounding hills without feeling rushed.  The schedule of your trip will adjust to your preferences, and not vice versa. You will decide how much structure each day has, so you never feel over or underwhelmed.  Whatever your needs may be, we will help you find the right balance for your Italian vacation.

Although all our culinary partners are exceptional, at The Italian on Tour your customized tour, there will offer the ability to visit Michelin-rated restaurants and have private meals in more exclusive locations.

Transportation will be in a private vehicle for your entire stay and the pick-up and drop-off to the airport or train station will also be included in your stay.


Here are just some of the possible experiences that can compose your tour:
  • Signature wine experiences with the original purveyor of the pecorino grapevine
  • A private tasting at one of Italy’s top organic and biodynamic wine producers with a chance to purchase vintages dating back to 1954
  • Shopping for shoes in Italy’s largest shoemaking area (outlets such as: Tod’s, Hogan, Prada, Armani)
  • Hands-on private cooking classes led by a locally renowned chef and sommelier, all set in the back drop of a 17th century villa
  • Visiting Urbino, a world UNESCO heritage site, and the birth place of Raphael who, along with Michelangelo and Leonardo da Vinci, is considered one of the great masters of the Renaissance period
  • Travelling through the countryside of Italy and getting to know a few of Italy’s “Beautiful Borgos” (small medieval towns situated on hilltops)
  • Dining at Italy’s and upcoming new restaurants
  • Enjoying award-winning wines while relaxing with friends and soaking up the beauty of our territory
  • Staying in historical luxury charm 4-star boutique accommodation in Ascoli Piceno, a city older than Rome!
  • Visit one of Hemingway’s former haunts, and sip a cappuccino in one of Italy’s 100 famous historical cafes while taking in the beauty of Ascoli’s famous Piazza del Popolo

Ready to design your trip?

the trip Collection


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