Wine Lovers Harvest Tour, September 12-18, 2021

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AN INSIDER EXPERIENCE for Wine Enthusiasts 

Authentic, hands-on and fabulously approachable, the Wine Lovers’ Harvest Tour features hand-selected 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.

Italy’s history and culture is steeped in wine. From one of Montepulciano’s top-notch Vino Nobile wineries to a local farmhouse where you’ll see how locals have been making wine for centuries, diversity is hands-down the magic of this amazing journey into Italian wine.


Although the focus of the Wine Lovers’ Harvest Tour is on wine, don’t think for a second that it’s all about wine! Since wine is an integral part of Italian culture, the two are quite simply inseparable. So this carefully crafted tour is also an immersion into Italian culture, history and (of course) food!

Get ready to explore medieval villages and interact with locals in a way that most travelers can only dream of.

And have your camera ready! You’ll be visiting some of Tuscany and Umbria’s most spectacular areas, with panoramas that will take your breath away. It’s like traveling in a living postcard.

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. Forget about stuffy wine classes and superficial tastings meant only to impress…Paola is not only down-to-earth, her philosophy about the enjoyment of wine, and the foods served along with it, is approachable, enjoyable and downright fun!

AN INSIDER EXPERIENCE for Wine Enthusiasts 

  • Dates: September 12-18, 2021
  • Accommodations at historic Villa Poggio alle Trese
  • Private ground transportation to/from Rome Fiumicino Airport
  • Private ground transportation to numerous wine cantinas (wineries) and medieval villages in Tuscany and Umbria
  • Fun, daily wine experiences with your own private sommelier
  • Hands-on participation in the local grape harvest
  • All breakfasts and most lunches
  • All dinners with food and wine pairings – plus menus you can adapt at home
  • Activities and experiences to remember for a lifetime
  • A few surprises!
  • Accompaniment by sommelier, Paola Donzelli, along with Pamela Haack and team Strada Toscana


Day 1 ~ Sunday, September 12: 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 13: 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 14: 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 15: 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 16: Città della Pieve  

  • Walking tour of Città della Pieve, saffron tasting, aperitivo in the piazza
  • Breakfast, lunch, dinner

After another delicious breakfast at the villa, it’s off to nearby Città della Pieve, where you’ll enjoy a fascinating walking tour with our friend, Bianca, of this beautifully preserved medieval hill town, including a look inside some ancient grottos, where wine has been made for literally centuries. After exploring, you’re in for a treat as we stop at our friend, Alessandro’s, saffron shop for a special saffron tasting and light lunch, along with a sampling of his exceptional organic wine, made from the vineyards that flank the villa where you’re staying. 

After lunch we head back to the villa for a bit of rest before returning to Città della Pieve to continue your guided tour with Bianca where you’ll learn about Renaissance artist, Perugino – born in Città della Pieve and teacher of Raffaello –  and view some of his precious masterpieces, followed by 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, we’ll meet up for aperitivo at one of Paola’s favorite places in the pizza before continuing to Lorenza’s restaurant for pizza night!

Day 6 ~ Friday, September 17: 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 “aperi-cena” with wine pairings.

Day 7 ~ Saturday, September 18: 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. Please note that although group transportation is provided to/from the airport in Rome, some of our guests choose to extend their stay in Italy before and/or after the trip. After you’ve registered, we’re happy to provide contact information for our favorite hotels in Florence, Rome and Venice – as well as a link to book train tickets.
  • Private transportation service to/from all towns and sites included in the itinerary
  • All abundant breakfasts, featuring fresh-baked Tuscan pastries, organic sheep milk yogurt, local cheeses, seasonal fruits, organic cereal, fresh eggs and cold cuts plus Italian caffè, cappuccino and herbal teas.
  • All regionally inspired dinners with local wines, along with menus carefully created with wine and food pairings in mind 
  • Most lunches
  • Daily wine related activities, including wine tastings, private cantina (winery) visits, participation in the grape harvest, wine & food pairings, lessons on Italian wines, vineyard walks and much more
  • Entrance fees
  • Private castle tour
  • Truffle hunt
  • Saffron tasting
  • Aperitivo and dinner in the vineyard
  • Pizza night!
  • Visit to 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.

Wine Lovers’ Harvest Tour