Autumn Wine and Food Experience

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AN INSIDER EXPERIENCE for Wine & Food Enthusiasts… 

… that is nothing less than an immersion into Italian culture – from family-run wineries and hands-on cooking classes, to shopping, exploring and dining in medieval hill towns. Plus the chef prepared meals, accompanied by top-notch regional wines, are truly exceptional!

Italy’s history and culture are inseparable from its food and wine, so you’ll enjoy private visits to a variety of cantinas in Tuscany and Umbria – the central regions of Italy where wine has been produced for literally thousands of years – along with seasonal, locally grown foods.

Plus you’ll explore medieval hill towns in some of the region’s most spectacular areas, with panoramas that will take your breath away.

THE REAL DEAL with Paola! 

And speaking of authentic, on your daily excursions and visits, you’ll be accompanied by delightful Paola Donzelli, a native Italian and sommelier who has been working in the world of wine for years, and is truly passionate about its history, its influence on Italian culture and its appreciation – along with just the right foods. Paola makes choosing and appreciating wines an enjoyable experience – and downright fun!


Day 1 ~ Sunday, September 18: Arrival

  • Tour of Villa Poggio alla Trese, trip orientation, aperitivo
  • Dinner

Benvenuti in Italia! Upon arrival at Rome Fiumicino Airport, sit back and relax as you are transported by private van service to the Italian countryside and Poggio alla Trese, your 17th century villa accommodations near the Tuscan town of Chiusi.

After check-in you’ll have the opportunity to explore your surroundings and learn some of the fascinating history of the both the house and the area. Then it’s time to join your own wine guide, and sommelier, Paola Donzelli, for an overview of the days ahead, while enjoying a classic Italian aperitivo. Afterwards, our own chef Lorenza, has prepared a delicious, regional-style dinner, which Paola has paired with a local wine. 

Day 2 ~ Monday, September 19: Parrano

  • Tour, tasting and grape harvest at Cantina Murogrosso, bruschetta lesson and olive oil tasting
  • Breakfast, lunch and dinner

This morning after a delicious breakfast featuring a variety of breads from the local pasticceria, sheep milk yogurt, organic honey, marmalades, seasonal fruits and more it’s off with to Cantina Murogrosso, a small production winery on the border between Umbria and Tuscany, where you’ll meet up with Paola. Make sure you’re wearing comfortable shoes that you can get dusty, because you’ll enjoy a tour of the vineyards before taking part in the actual vendemmia (grape harvest). So fun!

Afterwards, you’ll join Paola in the tasting room, situated above enormous fermentation vats, for a light lunch and wine tasting, featuring a variety of the estate’s wines, along with exceptional local products.

In afternoon, it’s back to the villa for some free time before gathering together fireside for an olive oil tasting, where you’ll learn the ins and outs of making true bruschetta over wood coals, before enjoying dinner together featuring regional dishes with an excellent wine.

Day 3 – Tuesday, September 20: Montepulciano

  • Walk in Vino Nobile vineyard, wine tasting in 14th century cantina, on your own in Montepulciano, gelato stop
  • Breakfast, lunch and dinner

This morning after another delicious breakfast, our private drivers will be transporting you into the heart of Tuscany’s spectacular wine country. First stop is our friend, Susanna Crociani’s, vineyards, planted with the famous grapes used to make the world-renowned Vino Nobile di Montepulciano. Next it’s on to her family’s with its fabulous 14th century wine cellars, where you’ll enjoy a special wine tasting in the atmospheric cantina itself, featuring the estates’s best wines, paired with a simple, delicious lunch. 

Afterwards, you’ll have the opportunity to explore the town of Montepulciano on your own. Be sure to check out the fabulous shops that flank the main avenues of town, as well as the alleyways that lead to spectacular views of the surrounding countryside.

In afternoon, on our way back to the villa, we’ll make making a stop at one of our favorite gelaterie in Montecchiello – a beautifully preserved medieval village, with sweeping views of the Val d-Orica, and one of the most photographed areas in all of Tuscany. This evening, you’ll enjoy apertivo with your fellow travelers, followed by dinner prepared by Lorenza, featuring Tuscan specialities that pair perfectly with Vino Nobile di Montepulciano.

Day 4 ~ Wednesday, September 21: Orvieto, San Casciano dei Bagni

  • Visit to Orvieto, enoteca Orvieto, vineyard aperitivo and dinner
  • Breakfast, dinner

This morning, after breakfast, we head to the ancient city of Orvieto perched on its stunning bluff overlooking the Val di Chiana, and with Etruscan foundations that date back nearby 3,000 years. Besides its rich history, Orvieto is known for its excellent white wine, Orvieto Classico. Here you’ll visit a typical enoteca of the area, situated in the town’s most picturesque piazza at the magnificent cathedral. Then, take some time on your own to explore the avenues and museums, and to visit inside the incredible 13th century duomo with its exceptionally preserved frescoes by Renaissance artist, Signorelli. Lunch is on your own at any one of the town’s inviting cafes or trattorie. 

Afterwards, it’s back to the villa for a bit of relaxation before heading to the medieval village of San Casciano dei Bagni. Here you’ll meet Daniela, and her family, who have invited you for apertivo and dinner in their vineyard – a short walk from the village itself. Along this picturesque route, we’ll be making a stop in an archeological park of ancient, thermal pools, where you’ll also see the ruins of a Roman temple, as San Casciano is a town situated over dozens of hot springs. Amazing!

Day 5 ~ Thursday, September 22: Città della Pieve  

  • Ciambelline lesson, walk in Città della Pieve, natural wine cantina, pizza night
  • Breakfast, lunch, dinner

This morning after a leisurely breakfast at the villa, you’ll be able to enjoy time on your own to relax poolside or take walk along the countryside lane. Then it’s time to join Paola for a fun ciambelline-making lesson before heading out to a local “natural” winery for a wine tasting and light lunch featuring organic foods from the area – all with a stunning, panoramic view. 

In the afternoon, it’s off to the nearby village of Città della Pieve for a visit inside the town’s historic cathedral and a look inside some ancient grottos, where wine has been made for literally centuries. Afterwards, enjoy some time exploring shopping and wandering on your own. Be sure not to miss Francesca’s organic shop, Sonia’s fashion boutique or Fema – an artisan shop that sells exceptional local gastronomic specialties. Afterwards you’ll join Paola for aperitivo in the piazza, before continuing to Lorenza’s restaurant for pizza night!

Day 6 ~ Friday, September 23: Montegiove 

  • Truffle hunt, private castle tour, estate wine tasting
  • Breakfast, lunch and dinner

This morning, after breakfast, you’ll be heading to meet the our friend, Lorenzo, the Marquis of the Castello di Montegiove, and to venture onto his private land with a local tartufaio – truffle hunter – and his truffle-hunting dogs. Here’s hoping we find some truffles! Afterwards, it’s back to the castle (which dates to the 1200s) to enjoy a private, guided tour of the castle and its wine cantina, with Lorenzo himself, followed by a light lunch and wine tasting, featuring the estate’s excellent wines – along with fresh truffles from our truffle hunt. Delicious!

In afternoon, we return to the villa where you can enjoy some free time to relax, take a dip in the pool or walk the countryside lane before joining Paola for a special farewell aperitivo and dinner with wine pairings.

Day 7 ~ Saturday, September 24: Departure

Our drivers will be transporting you this morning to Rome Fiumicino Airport.



Your accommodation are Poggio alle Trese, a 17th century villa, nestled along the border of Tuscany and Umbria, near the town of Chiusi (Tuscany). The villa boasts two kitchens, several lounge areas, dining hall, breakfast hall, sleeping rooms decorated with family antiques, swimming pool, outdoor patios, barbecue “house”, gazebo, wisteria-covered aperitivo terrace and so much more… View photos of Villa Poggio alle Trese here. 


  • 7 days/6 nights at elegant Villa Poggio alla Trese, situated in the picturesque countryside near the charming Tuscan hill town of Chiusi
  • Group transportation by private van service to/from Rome Fiumicino Airport on arrival and departure dates. 
  • Private transportation service to/from all towns and sites included in the itinerary
  • All breakfasts
  • All regionally inspired dinners with local wines, along with menus carefully created with wine and food pairings in mind 
  • Most lunches
  • Daily wine and food-related activities, including private tastings, exclusive tours and visits, participation in the grape harvest, wine & food pairings tips, lessons on Italian wines and foods,  and much more
  • Truffle hunt
  • Saffron tasting
  • Aperitivo and dinner in the vineyard
  • Pizza night!
  • Visit to an enoteca
  • Evening aperitivo hour for chatting, sharing and relaxing
  • Activities and experiences to remember for a lifetime
  • A few surprises!
  • Accompaniment by sommelier, Paola Donzelli, along with Pamela Haack and team Strada Toscana

Not included: Airfare, meals, alcoholic drinks, buses, trains or boat transportation outside of that which is specifically listed in the trip package, trip cancellation insurance, gratuities for villa staff and drivers

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. The quality of the trip is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.


  • Dates: September 18-24, 2022
  • Trip Price:
    • $3,040 USD per person, double occupancy with ensuite bathroom
    • $3,040 USD per person, single occupancy with shared bathroom (max 2 of same gender per shared bathroom)
    • $3,240 USD per person single occupancy with ensuite bathroom
  • $500 deposit is required to secure your space on this trip
  • View our Terms, Conditions and Cancellation policy here