Tuscany & Umbria

7 Nights/8 Days

Starting From $3000


Explore the central Italian regions of Umbria and Tuscany, the latter of which is one of the most popular tourist destinations in the country. Populated with sloping hills covered with vineyards, luscious green woods, idiosyncratic medieval villages with their own peculiar features, and spectacular valleys, this area of the country is famous for its long tradition of producing some of the best Italian wines, olive oils, cheeses and meats. Start off in the famous Chianti region, where wine is a religion, before passing through the beautiful town of Siena – home of the famous and sometimes fatal Palio horserace - as you head south. Reach the romantic Val d’Orcia to admire its Tuscan landscapes, dive into its woods to hunt for truffles, and then learn how Italian “nonni” make the local “pici” pasta. Top your experience off with an indulgent visit to the Perugina chocolate factory in Perugia: the icing on the cake for this astounding adventure through central Italy.


Arrive in Florence and be privately transferred to your hotel in the renowned Chianti region. Here you will be warmly greeted by your host and be able to relax after your flight with a welcome aperitif. After unpacking, head to a boutique winery for a delicious welcome dinner. Overnight in Radda in Chianti.
*Transfer from Rome Airport also available with a small supplement.
Meals : Welcome Dinner
Head out for your first day in the beautiful Chianti landscape, which is dappled with vineyards, olive groves and plentiful medieval castles. Make your first stop at Badia di Passignano, a unique wine estate where you will enjoy a tour and a tasting, before indulging in a traditional Tuscan lunch. Next you will head to Greve in Chianti for a walking tour, where you will discover the town’s medieval streets and piazzas, Piazza Matteotti being one of the highlights. You will then get the chance to explore Greve’s Wine Museum, where you will learn about Chianti’s heritage and deep-rooted traditions by observing many historic artefacts collected from the surrounding areas. After this educational experience, head to Castello di Verrazzano, where Giovanni da Varrazzano, the explorer who discovered the Bay of New York, was born in 1485. Then enjoy a well-deserved dinner in a rustic farmhouse before heading back to your hotel to rest and prepare for tomorrow’s adventure. Overnight in Chianti.

Meals : Breakfast, Lunch, Dinner, Wine Tasting
In the morning, visit the beautiful town of Siena, the city which famously warred with Florence for dominance and also hosts the famous, sometimes fatal, Palio horserace. Then enjoy lunch at farm that produces the popular pecorino cheese, before heading to Volpaia, a historic village with wine running through the heart of it - literally, as a network of pipes transport wine across various buildings that comprise the winery, like veins pumping the hamlet’s life source around it! Here you will enjoy a delicious dinner in a farmhouse before heading back to your accommodation. Overnight in Chianti.
Meals : Breakfast, Lunch, Dinner
Head south in the morning towards Valdichiana, passing through the magnificent Valdorcia along the way. You will see breath taking and iconic views of luscious green rollinghills, rolls of haystacks dotted along the fields, medieval castles, ancient hilltop towns, charming rural farmhouses, neat rows of vineyards, cypress tress and golden wheat fields, making the journey more than just a means of getting from A to B! En-route you will stop off in the villages of San Quirico d’Orcia and Bagno Vignoni (famous for its hot springs), which have both been renowned since the Middle Ages due to their positions on the old via Francigena – the route pilgrims followed from Canterbury to the Holy Land. After a busy afternoon exploring, enjoy dinner served in an outstanding estate located near Montepulciano. Overnight in Montepulciano.

Meals : Breakfast, Dinner
Start your day with an exciting truffle hunt in the Valdichiana Senese woods, where – accompanied by a professional truffle hunter who will tell your stories and legends of the area - you will experience first-hand what an intense experience searching for the fancy fungi can be. Then, to top the experience off, enjoy a truffle infused lunch before heading to a rustic Tuscan farmhouse for a wine tasting, followed by a cooking class. Here you will learn to prepare pici pasta, the most famous pasta dish in the province of Siena. Overnight in Montepulciano.

Meals : Breakfast, Lunch, Dinner
In the morning, visit the fascinating Avignonesi winery in Cortona, which is unique due to producing its wine with innovative biodynamic and organic methods. Here you will enjoy a typically Tuscan lunch, before heading to Montalcino – which is famous for giving its name to the high-quality Brunello di Montalcino wine – in the afternoon for a walking tour. You will also experience an exquisite wine and cheese tasting in the town, accompanied by local producers. In the evening, you will enjoy a romantic dinner, charmingly located in the courtyard of a stunning villa. Overnight in Montepulciano.
Meals : Breakfast, Lunch, Dinner, Wine Tasting
Pass along Lake Trasimeno as you make your way to the region of Umbria. Here you discover where the well-known Montefalco and Sagrantino wines are produced, before enjoying a lunch in the town of Passiganno del Trasimeno. Then, you will head to the picture-perfect city of Perugia, where you will be able to indulge in the Wonka-esque world of Perugian chocolate. Visit the city’s chocolate museum to get some informative information, before heading into a chocolate factory itself to see first-hand how the sumptuous sweet is made. Make your way out of Perugia and head to the Italian capital where you will arrive late afternoon. Take some time to relax in “the Eternal City” before enjoying a final farewell dinner in Trastervere – a bohemian area of the diverse city. Overnight in Rome.
Meals : Breakfast, Lunch, Dinner
Bid farewell to Italy as you are transferred to Rome Fiumicino Airport.
Meals : Breakfast

Departure Dates/Pricing

Dates Double Single Triple
Sat 21 September '19
Sat 19 October '19
Sat 23 May '20
Thu 02 July '20
Sat 19 September '20
Sat 14 November '20
* Rate in US$, per pax


  • Learn the secrets of expert winemakers
  • Hunt for truffles with a legendary “trifolaio” (truffle hunter)
  • Enjoy wine-tastings in authentic farmhouses and historic wineries, where delicious vino is paired with cheese and salami to create a taste sensation
  • Visit ancient wineries including Antinori and Verrazzano, which have played a pivotal part in the development of Italian wine
  • Discover the “religious” wine tradition of Chianti
  • Immerse yourself the delightful Val d’Orcia
  • Explore the ancient streets of walled medieval towns
  • Meet Italian “nonni” and learn how to make “pici” pasta at a local farmhouse
  • Visit the Perugina Chocolate Factory in Perugia and indulge in the sumptuous Wonka-esque world Perugian chocolate
  • Visit the unique Avignonesi winery, which produces delicious, high-quality wine through innovative biodynamic and organic methods
  • Relax in the tranquil setting of a Tuscan spa

What's Included

  • A visit to the chocolate museum in Perugia
  • 1 “pici” cooking class
  • 1 truffle hunting
  • 2 wine tastings paired with artisanal cheeses and charcuterie in local wineries
  • 7 dinner in local farmhouses, wineries and restaurants
  • 5 lunches in local farmhouses, wineries and restaurants
  • Guided visits of Greve in Chianti, Siena, San Quirino d’Orcia, Bagno Vignoni, Montalcino, Perugia
  • 1 night in Rome
  • An expert tour Guide
  • 3 nights in Montepulciano
  • 3 nights in Chianti
  • Transfers as per itinerary
  • Daily breakfast

Tour Information

Tour Code: CT03
Tour Type: Small Group Journeys
Tour Category: Food & Wine Tours
Departure Type: Guaranteed Departure
Starting Point: Florence, Italy
Ending Point: Rome, Italy
Grade/Difficulty: Moderate
Duration: 7 Nights/8 Days
Transport Mode: Walking + Car/Minivan
Scheduling: Small Group Fully Escorted
Languages: English
Children Allowed: Yes
Min. Pax: 2
Max. Pax: 18


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