8 Days Self Drive Food and Wine Tour of Tuscany from Rome

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Escorted Tours
difficulty Very easy
Wheelchair Not Accessible

8 Days Self Drive Food and Wine Tour of Tuscany from Rome

Depart for a fascinating Self Drive Tour, in a region that holds more than 2000 years of history, Tuscany. During 8 days, you will live art, culture, food and traditions, tasting delicious local specialties.

Let the art of the "Cradle of the Renaissance”, Florence, enchant you
Set your cooking talent free, during our Cooking Lesson
Taste the most famous wines of Tuscany
Explore the heart of Chianti and the beauties of Siena, San Gimignano, Montepulciano, Pienza and Montalcino
Dine in some of the traditional restaurants of Tuscany

Day 1 – Rome

Arrive at Rome Leonardo da Vinci International Airport and reach your hotel in the heart of this Eternal City. Spend the day at leisure. Overnight stay in Rome.

Day 2 – Rome, Florence

Depart to Florence after breakfast. Check into your hotel and tour the city center. The main attractions of Florence tend to be within walking distance. Marvel at the beautiful Duomo, Piazza della Signoria and Ponte Vecchio. Indulge in a delectable dinner at an authentic local restaurant serving superfine Italian specialities. Overnight stay in Florence.

Day 3 – Florence

After breakfast, meet your guide and embark on your guided walking tour of the core of Italian Renaissance. Refresh yourself at one of Florence’s oldest ice cream parlours that has a variety of 33 different flavours and its utilization of top local produce, including pistachios from Bronte, a Slow Food Presidium product, saffron and cardamom. In the afternoon, we will enrol in an enriching cooking class in the historical city center followed by a light dinner. Overnight stay in Florence.

Day 4 – Chianti area

Make your way to Tuscany after breakfast. Dedicate the day to enjoy the marvellous Chianti hills, situated along the Via Chiantigena (an ancient road connecting Siena with Florence). Meet the winemakers of the Biodistretto (Bio district) at Tenuta Fontodi in Panzano for a tour of the cellars and tasting session. Head over Greve in Chianti and sample some delicious salami at Antica Macelleria Falorni. After which, we will enjoy some organic cheeses (including baby goats cheese and fresh ricotta) at Podere Le Fornaci, where they manufacture these cheeses from the milk of the goats that graze in the Chianti hills. In the afternoon, we will learn about cashmere making, from its origins to the end product of hand weaved accessories at a small bucolic farm. Head back to Greve and spent the rest of the day at leisure. Indulge in a delectable dinner at Trattoria Mangiando Mangiando (or in a similar structure) before returning to your hotel in Chianti for an overnight stay.

Day 5 – Siena and San Gimignano

In the morning, depart to Siena, a city with one of the most distinguished medieval architectures in all of Italy. Stroll through the alleyways of this enchanting city, marvelling at its gothic architecture and art-filled piazzas.
Check out the famous site of Siena’s horse race, the Palio at Piazza del Campo. Drop by the many famous patisseries and try out delectable traditional sweets such as the Panforte. Shop at leisure. Along the way to San Gimignano and passing by the ancient Via Francigena, grab lunch prepared by some of the traditional local produce such as the Certaldo onion (Slow Food Presidium), and the organic extra virgin olive oil from San Gimignano at the cozy farmhouse Il Castagnolino. Be enlightened by the professionals here on the process of manufacturing organic olive oil. In the afternoon, we will join a guided visit of San Gimignano, one of the most intact medieval villages in Italy. Keep your eyes peeled at the many imposing ‘skyscrapers’ of the 13th and 14th centuries. Wander through the narrow and characteristic streets leading up to the top of the village for breath-taking views of the city’s surroundings. Pop by one of the many quaint cafes in the area and sample fine local Vernaccia wine. Return to the hotel and retire for the night.

Day 6 – Montepulciano and Pienza

Depart for Montepulciano in the morning. Montepulciano is one of the most charming and well-preserved medieval villages. Perched on a cliff 605m above sea level, this city offers stunning panoramic views over the surrounding hillsides. Head down to the Enoteca Contucci winery for a free tasting session and discover the magnificent town center. We recommend going over to the old Osteria dell’Acquacheta for lunch due to its rustic and familial atmosphere. Try out some of Tuscany’s best cuisine, such as the Pici all’Aglione. Depart for Pienza, the epitome of a renaissance city renowned for its Pecorino cheese. Visit a Pecorino cheese factory and discover the secrets of cheese making and some sampling. Return to the hotel for an overnight stay in the Chianti area.

Day 7 – Montalcino, Florence

Make your way to Montalcino, world-famous for its Brunello, one of the most excellent red wines in the world. Montalcino boasts over 3,000 hectares of vineyards, half of which is dedicated to fermenting Brunello.  Drop by Mastio della Rocca, home to the Enoteca La Fortezza to purchase some exceptional local produce, delectable honey and sample some fine wines. Have a delicious lunch at Osteria di Porta al Cassero in Montalcino. After which, shop at leisure. In the afternoon, we will visit one of the leading wine manufacturers in the region for wine sampling and a guided tour of their cellars. Head back to Florence and retire for the night.

Day 8 – Departure

After breakfast, head to Florence Airport for your return flight.

  • Rome
  • Florence
  • Chianti
  • Siena
  • San Gimignano
  • Montepulciano
  • Pienza
  • Montalcino
  • Florence
  • Departure
  • 7 nights in hotel 4*
  • Breakfast
  • Private guides as per program (Florence, Siena and San Gimignano)
  • Dinners and lunches as per program
  • Tastings of local products, wines and oils as per program
  • Cooking class in Florence
  • Visit to Chianti Cashmere Farm
  • Trasport
  • City taxes
  • Tips (optional)
Meeting point: 

Meeting point information and local telephone numbers at your destination are included on your Confirmation Voucher.


We suggest wearing comfortable clothes and shoes.
Please note that transportation is not included. If you need to rent a car, please contact us for a quote.
Kids under 2 years old travel for free.

Confirmation will be received within 48 hours of booking, subject to availability. Once your booking is confirmed we will email you a voucher. This is your ticket and proof of purchase.