Ascoli Piceno

Taste of Italy

Ascoli Piceno
Dates From
4 nights
5 days
Price From
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Embark on five fantastic days of farm-to-table cuisine and fabulous wine in the up and coming region of Le Marche, Italy.  Set in the backdrop of enchanting medieval villages, truffle territory, and national parks, you will be able to relax and fully immerse yourself in the “Bel Paese”. Unpack once and unwind with a luxury boutique stay in the heart of Ascoli Piceno’s historic centre. Indulge in tasting award-winning wines, a fun hands-on cooking class, and world-renowned regional delicacies, on an itinerary that will give you a true taste of Italian life. Not only will you meet local experts, learn from an Italian chef, but you will also be joined by a Fully-bilingual, 100% Italian, 100% local guide with an International culinary resume.  His expertise and passion for sharing our acclaimed region of Italy will ensure your trip is filled with memories to last a lifetime.  Escape the crowds and travel deeper with a journey of authentic Italy that you have always dreamed about.


  • Four nights double occupancy stay in 4-star Luxury boutique historical accommodations with ensuite bathroom
  • Daily breakfast with local ingredients
  • 5 Meals including wine, coffee and dessert
  • A Private Hands-on cooking class including all your creations to take home
  • A Privately guided walking tour of Ascoli Piceno with a local expert
  • A Wine Tasting Experience
  • A Privately guided walking tour of Offida with a local expert
  • Visits to some of Italy’s Borghi Piu Belli d’Italia
  • Services of your own private Italian on Tour Guide
  • Expert Pre-Trip Travel Advice
  • All coffee and gelato when you are with your Italian on Tour Guide
  • All special events, private tours, and local experts as per itinerary
  • All entrance fees
  • Departure day transfer your hotel to Ascoli Piceno’s train and bus stations
  • Airport pick-up/travel from from Rome’s Fiumicino Airport to Ascoli Piceno
  • All gratuities for drivers, local guides, and service at meals
  • Gratuities for your Italian on Tour Guides
  • Taxes, tips, and service charges


Day 1: Rome to Ascoli

Welcome to Italia! Meet your guide and enjoy a comfortable ride in our private vehicle from Rome’s Fiumicino Airport directly to Ascoli Piceno. No need to wait for buses or taxis, just hop on with your guide and arrive directly at your hotel. Enjoy the scenery of the National Park on the way or simply nap to recover from your jet lag! We will stop on the way for a quick lunch to taste the best panino from Ascoli to Rome. In the late afternoon arrive to Ascoli and settle into your home for the duration of your stay. Your Hotel is located just a stone’s throw away from one Italy’s most beautiful Piazzas making it the perfect location to relax and explore the city by foot. Before dinner meet up with your guide and trip designer for an optional mini-orientation tour of Ascoli Piceno.  After, take in a relaxing evening with a glass of Rosso Piceno (a variety of local red wine) and enjoy your first dinner with your fellow travellers and new-found friends.

Meals: Lunch, Dinner

Activity: Optional pre-dinner stroll to get acquainted with Ascoli Piceno’s historic centre (time-permitting).

Day 2: The Sweet Life

Every day will begin with a delicious breakfast, composed of local products and seasonal pastries, served in the elegant courtyard of your hotel. Your guide will always meet-up with you at your hotel before embarking on the adventure of the day. This morning let’s take a bite out of the sweet life by saying Buongiorno (Good day) to wine country and one of Italy’s most beautiful hill-top villages!  We will drive east down countryside roads to make our first stop of the day: Offida, one of Italy’s Borghi piu belli (most beautiful villages).  Step back in time as we stroll through this quaint town working up an appetite for an afternoon full of wine tasting and true zero-km dining. Bid Arriverderci (goodbye) to Offida’s Old-World charm and Hello to wine and dining Italian style. Today you will meet one of the owners, whose father is the original purveyor of the pecorino vine. She will take you on an exquisite journey of the taste buds, pairing local charcuterie, and rustic dishes with award-winning wines. After a leisurely lunch, you will make your way from the Cantina to the beautiful Vigneto Storico (Historic vineyard) where you have the opportunity to savor your last sip completely immersed in wine country. In the late afternoon, we will return to Ascoli. Your evening is free.  Relax, take an evening walk, and enjoy dinner on your own at one of Ascoli’s many local hotspots.

Meals: Breakfast, Lunch accompanied by wine taste/pairing at an award-winning winery

Activity: 2-3 hours guided walking tour on cobble stone streets, and a leisurely stroll through the vineyards (weather permitting)

Day 3: Italian Cooking 101

Wake up and ease into your day with a relaxing breakfast. Your guide will meet you at your hotel and whisk you away into the Italian countryside for a cooking class at a 17th century villa that once had its life as an abbey.  Admire its beautiful frescos while you get a hands-on cooking lesson from a locally renowned chef that learned her secrets from the best, Nonna (Grandma).  After cooking up a storm take some time to enjoy the fruits of your labor and breathe in the tranquility of this peaceful property with a lunch in the gardens and relaxation by the villa’s pool. In the late afternoon, your guide will meet you at the villa and you will return to Ascoli. The evening is yours to relax, take a stroll, and eat some delicious Italian fare.

Meals: Breakfast, Lunch, and the creations made in your cooking class (please note that the cooking class menu varies with the season in order to offer you the freshest and most flavorful taste of the local cuisine)

Activity: 2-3 hours standing on your feet in the morning during your hands-on cooking class, in the afternoon relaxing poolside (weather permitting)

Day 4: Ascoli Piceno, the City of Travertine and 100 Towers

Today you will meet your local guide and resident Ascolana (Person from Ascoli Piceno) for a privately guided walking tour of Ascoli Piceno, which is heralded for one of the most beautiful squares in all of Italy! By foot we will explore Ascoli’s magnificent piazzas, and visit the beautiful Duomo, all while learning about the art, culture, and history of the powerful people called the Piceni. After working up an appetite we will travel to the land of Tartufo Nero (Black Truffle) for lunch at a family-run establishment where Nonna is known for making the best Olive Ascolane (stuffed olives) in this neck of the woods. After a leisurely lunch with your fellow travellers, we will travel through the countryside to the foot of the Sibillini mountains.  We will enjoy a walk through one of our local mountain villages which was once an old Roman outpost and then make our way to a beautiful panorama of central Italy’s majestic mountain range. In the early evening we will return to Ascoli.  The evening is free to relax, pack your things, and enjoy one last passeggiata (stroll) through Ascoli’s beautiful town squares.  Dinner is on your own.

Meals: Breakfast, Lunch

Activity: 3-3.5 hours urban walking in the morning, late afternoon stroll and sightseeing

Day 5: Arriverderci!

After a final breakfast, it is time to say goodbye to your Italian on Tour guides and your new-found friends. You will be driven to Ascoli’s bus or train station connecting you to the next leg of your trip. Should you wish to stay longer in Ascoli or explore Rome, Florence, or elsewhere, your guides will be happy to help you book your own alternate travel arrangements. Until next time “Arrivederci”!

Meals: Breakfast


Starts Ends Price Status Book
09/07/201913/07/2019$3250 p/p twin shareFully Booked
28/07/201901/08/2019$3250 p/p twin shareOn Request
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17/09/201921/09/2019$3250 p/p twin shareOn Request
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08/10/201912/10/2019$3250 p/p twin shareFully Booked
22/10/201926/10/2019$3250 p/p twin shareAvailable
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10/11/201914/11/2019$3250 p/p twin shareAvailable
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15/11/201919/11/2019$3250 p/p twin shareAvailable
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20/11/201924/11/2019$3250 p/p twin shareAvailable
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25/11/201929/11/2019$3250 p/p twin shareAvailable
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Travel to and from Italy, travel insurance, any other meals not noted in the itinerary, excursions not listed above and any items not mentioned in the itinerary.
Prices subject to currency fluctuation.