A tour to 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 worldwide for their prestigious wines and 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.

During your holiday, you will have the unique chance to sample several Slow Food Presidia products – high-quality, traditional foods and beverages at risk of “extinction” – and other local delicacies from Slow Food’s recommended quality producers of food, wine and one of Florence’s oldest ice cream parlours – Perché no! (Translated Why not?!). You will also have a chance to taste delicious, authentic dishes of the regional cuisine when eating at restaurants selected from the Slow Food in the Osterie d’Italia guide – small trattorie that still use fresh, local produce and traditional recipes for their dishes. You will also sample wines and/or local typical products at wineries, bakeries, pastry shops, fresh produce markets and more in Montepulciano and Montalcino vineyards.

The tour is not just about food and drink, however, as it also takes in historic monuments, works of art, churches and natural landscapes of the region – from Florence to Siena, San Gimignano, a UNESCO World Heritage site, with its wonderful medieval towers and the San Gimignano 1300 Museum to Pienza, the perfect example of a renaissance city, famous for its Pecorino cheese. All surrounded by the beautiful hills and vineyards of Chianti and Tuscany.


Your Itinerary

Day 1: Arrival

Arrival in Florence Airport. Private transfer to the hotel in Chianti Area. Time to settle in, welcome dinner in hotel and overnight stay. (D)

Day 2: Florence

Morning departure with private car to Florence. Meet your local guide for a half-day private 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 and a precise selection of raw materials (including pistachios from Bronte, a Slow Food Presidium product, saffron and cardamom). Return to the hotel and overnight stay. (BB, L)

Day 3: Siena, San Gimignano

Morning departure by private car to Siena. Meet your local guide for a full-day private tour of Siena & San Gimignano. Siena is a city with some of the most important and most beautiful architecture, including the Museum delle Contrade (each horse in the famous “Palio”, runs for a different Contrada or district). We suggest sampling 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 (Slow Food Presidium), and the 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, to visit the famous towers and the San Gimignano 1300 Museum: 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

The entire day is dedicated to discovering (in your private car) 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 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 a historical butchers, where since 1729 they have produced the specialties of the local [norcineria], the Prosciutto Saporito (Cured Ham) di Greve and all types of cured products from the surrounding Senese hills, as well as wild boar, from the well-known Finocchiona to the Noble Salamis of Chianti and Classical Chianti. We recommend a typical trattoria for lunch. In the afternoon you visit 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 in your private car to Montepulciano, one of Italy’s most characteristic and intact medieval cities, which from a height of 605 metres above sea level, offers amazing views over the surrounding hillsides. Visit a typical winery for a free tasting, and then explore the wonderful town centre of Montepulciano. We recommend a rustic, family-owned osteria for lunch, where you may sample some of Tuscany’s best recipes (such as the Pici all’Aglione). In the afternoon, we 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 in your private car to 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 exceptional honey, a local speciality. Free time. Return to the Florence area and join a cooking class dedicated to the Tuscany tradition, followed by dinner. Overnight stay at the hotel. (BB, C, D)

Day 7: Departure

After Breakfast, check out and private transfer from the Hotel to Florence Airport. (BB)





Moxley & Co special inclusions

  • Welcome dinner
  • Private tour of Florence with lunch in a typical local restaurant
  • Full-day private guided tour of Siena
  • Full-day private guided drive in Chianti hills
  • Private guided tour of Montepulciano
  • Wine tasting
  • Private guided tour of Montalcino
  • 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 £3,306 per person, including international flights from the UK, accommodation, a private car with a guide, tours and experiences as shown based on two sharing.