This leisurely self drive tour offers a unique journey through Tuscany. Tuscany has been popular with visitors for many years. This itinerary enables you to sample the highlights of this part of Italy with the benefit of the local knowledge of our partner in Italy. You will explore a region of sprawling vineyards, rolling hills, charming old cities, masterpieces of art and gourmandise: visit magnificent Florence, the “Cradle of the Renaissance”, Siena, famous for the Palio horse race, the Chianti area, Montepulciano and Montalcino, known all over the world for their prestigious wines, San Gimignano with its tall towers. Visit wineries and cellars, sample excellent wines, rare cold cuts, Pecorino cheese and olive oil and shop for delicacies in the many food shops.

Italy Tuscan countryside

Discover Tuscany – Curated Self Drive AG14

During the tour, the participants will not only discover delightful food and wines but also the most interesting monuments, works of art, churches and natural landscapes of the region:

Private walking tour of Florence, the cradle of the Italian Renaissance, and the Ponte Vecchio bridge, followed by lunch in a local restaurant as well as cooking lesson and dinner on a separate day

Siena, where the famous Palio race is run in the ancient Piazza del Palio square

San Gimignano, a UNESCO World Heritage site, with its wonderful medieval towers and the San Gimignano 1300 Museum, with visit to local farm with light lunch.

the Chianti area, with its wonderful hills and vineyards, where some of the best Italian wines and food are produced. Tastings of local produce are included.

Montepulciano, one of the most characteristic and intact medieval cities in Italy, where we include a tasting of local cheeses

Pienza, the perfect example of a renaissance city, famous for its Pecorino cheese

Montalcino, a beautiful art city which is famous for its Brunello, one of the best red wines in the world

Italy Florence
Italy – Florence

Florence area 7 nights |

Your itinerary

Day 1 – Arrival

Arrival at your hotel near Florence. Time to settle in before a welcome dinner and overnight stay. (D)

Day 2 – Florence

Morning departure for Florence. Private guided tour of Florence. Walk through the historical centre of this amazing city and visit the Santa Croce church (outside), known as the “Pantheon of Italian Glories” where many illustrious Italians such as Michelangelo, Galileo, Rossini and Machiavelli are buried. The visit also takes in the other religious buildings (the Baptistery, the Duomo and Giotto’s bell tower – outside) and the houses of power in the old city (the Piazza della Signoria). Lunch at typical restaurant. Free afternoon to stroll along Florence elegant streets. We suggest a break at one of Florence’s oldest ice cream parlours that offers more than 33 different flavours. Return to the hotel and overnight stay. (BB, L)

Day 3 – Siena, San Gimignano

Morning: we suggest to visit Siena, one of the most important and most beautiful architecture in the city, including the Museum delle Contrade (each horse in the famous “Palio”, runs for a different Contrada or district). We suggest to sample of some delicious traditional desserts like the Panforte in one of the most famous pastry shops in town. Free time for shopping. On the way to San Gimignano along the ancient Via Francigena, lunch with some of the traditional local produce such as the Certaldo onion and organic extra virgin olive oil from San Gimignano in a little family-run farmhouse. Visit and have a talk on the techniques used in producing organic olive oil. We suggest, in the afternoon, a visit to the famous towers and the San Gimignano 1300 Museum with its storyboards, multi-media exhibits, street scenes and a ceramic recreation of the city as it was back in 1300. Return to the hotel and overnight stay. (BB, LL)

Day 4 – Radda in Chianti, Greve in Chianti

Entire day dedicated to discovering the Chianti hills along the Via Chiantigena (an ancient road connecting Siena with Florence crossing over the Chianti hills). Visit a winery in Radda in Chianti where you will meet the wine producer and visit to the cellars, at the end enjoy a wine tasting. Proceed to Greve in Chianti where we suggest visiting the little historical town centre. Stopping at the historical butchers where since the 1729 they have produced local specialities such as Prosciutto Saporito (Cured Ham) di Greve, cured products from the surrounding Senese hills as well as the wild boar from the well-known Finocchiona to the Noble Salamis of Chianti. We suggest you make time for a tasting of salami. We can recommend a local Trattoria where you can take lunch. In the afternoon we have scheduled a visit to a winery in Greve in Chianti for a wine and oil tasting. Return to the hotel and overnight. (BB, T, T)

Day 5 – Montepulciano, Pienza

Morning departure for Montepulciano, one of the most characteristic and intact medieval cities in Italy which from a height of 605 metres above sea level offers amazing views over the surrounding hillsides. Visit typical winery for a free tasting, and then explore the wonderful town centre of Montepulciano. For lunch, we recommend a traditional, local Osteria with its rustic and family run atmosphere. Here, you may sample some of Tuscany’s best recipes (such as the Pici all’Aglione). In the afternoon, proceed to Pienza, the perfect example of a renaissance city, famous for its Pecorino cheese. Visit a Pecorino cheese producer, learn something about the cheese-making process, and sample the fare. Return to the hotel and overnight stay. (BB, T)

Day 6 – Montalcino

Morning departure for Montalcino, famous for its Brunello, one of the best red wines in the world. Montalcino, however, is also a beautiful art city, which dominates 3,000 hectares of vineyards (1,500 for Brunello alone). We suggest a visit to the Mastio della Rocca which is home to the Enoteca La Fortezza where it will be possible to buy some local products and the exceptional honey, a local speciality. Free time. Return to Florence area and join a cooking class dedicated to the Tuscany tradition, followed by dinner. Overnight stay to the hotel. (BB, C, D)

Day 7 – Departure

Departure (BB)


Moxley & Co special inclusions

  • Private walking tour of Florence.

  • Welcome dinner

  • Lunch in typical local restaurant

  • Cooking lesson followed by dinner

  • Wine tasting

  • Regional food tastings

Indicative prices

All of our holidays are individually tailored to suit your needs and timescale.

As a guide, this 7 day suggested holiday will cost from £1,499 per person including international flights from UK, accommodation, car hire, tours and experiences as shown based on two sharing.