Discover Tuscany – Curated Self-Drive

** Premium Itinerary with local insights **

Trip Commences and finishes: Florence, Italy | 7 day premium itinerary | From £1,499pp

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.


Detailed Itinerary

Day 1: Arrival

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

Meals: Dinner

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.

Meals: Breakfast, lunch

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.

Meals: Breakfast, light lunch

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.

Meals: Breakfast, two tastings

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.

Meals: Breakfast, tasting

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.

Meals: Breakfast, cooking class, dinner

Day 7: Departure


Meals: Breakfast

Important Details

Program may be subject to change depending on the availability of the local excursions the opening of the sites, which may vary in accordance with time of the season.

What’s Included:

  • 6 nights accommodation in Tuscany on bed & breakfast basis
  • Private walking tour of Florence
  • Welcome dinner
  • Lunch in typical local restaurant
  • Cooking lesson followed by dinner
  • Wine tasting
  • Regional food tastings
  • International flights departing UK

This 7 day itinerary starts at £1,499 per person and all holidays can be tailored to your exact needs. 

To discuss and plan your incredible trip to Tuscany with a destination expert, please follow the link below and our travel partner will be in touch.

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