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Chianti Walking & Wine
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At a glance
Experience the magic of Italy in Tuscany
Trip Highlights
Start Destination
Castellina in Chianti
End Destination
Castellina in Chianti
What's included
  • All breakfasts
  • 5 dinners
  • 3 wine tastings
  • All accommodation (see below)
  • All transport and listed activities
  • Tour leader throughout
  • Flights from London (if booking incl. flights)

All breakfasts 5 dinners and 3 wine tastings are included. Breakfast is usually a continental style buffet. Of the 5 included dinners, three are taken at Villa Casalta and a reasonable amount of wine is included. Two are taken in local restaurants (drinks not included). Vegetarian choices are available - please advise us of dietary requirements on booking.

Day 1
Fly to Pisa
Fly to Pisa; transfer to Villa Casalta.
Day 2
Visit the mediaeval market town of Greve in Chianti and the hilltop village of Montefioralle; afternoon wine tasting.
We head to the mediaeval market town of Greve in Chianti walking through a magnificent setting of olive groves and vineyards. On the way, we will stop in the fortified hilltop village of Montefioralle, considered the most ancient 'borgo' in Chianti. We return to our farmhouse in time for a tasting of the local wine before dinner. Total walking approx. 9 km
Day 3
Travel to Siena and explore the stunning historic centre; learn about Tuscan and Italian wines at the Wine School.
Using a combination of bus and train we make our way to the centre of Siena for a day exploring this fascinating city. We have time for visits to the numerous museums and stunning Duomo, to relax in one of the many outdoor cafés in the main square, the Piazza del Campo, home of the world famous Palio horse race, and a visit to one of the many boutique shops specializing in local products and cutting edge Italian fashion. In the afternoon we also have the fantastic opportunity to learn about Tuscan wines on a 2-hour fun interactive course at the Tuscan Wine School.
Day 4
Circular walk from our lodge to the tiny village of Fonterutoli and back to Castellina.
This morning we will set out for a local history walk, covering the route from Villa Casalta to Castellina in Chianti before breaking for lunch in charming Castellina. This afternoon we take a short bus ride to start our walk around picturesque Fonterutoli; famed for acclaimed Chianti Classico wine. We will take a stroll through local woodlands where we may be lucky enough to spot the prized Cinta Senese Tuscan pigs! Total walking approx. 12 km
Day 5
Free day.
Today is free to rest any potentially tired legs at the poolside. Alternatively, your leader can advise on local Chianti wine tasting tours and cooking classes, offer assistance for unguided walks, or help you plan a day trip to Montepulciano.
Day 6
Discover the magnificent city of Florence, considered the birthplace of the Renaissance.
Our destination today is the magnificent city of Florence, the birthplace of the Italian Renaissance with an enormous wealth of historical sites, museums, galleries, churches and architectural delights. Most of the great artists, thinkers and builders from Renaissance history passed through or lived in Florence when it was under the rule of the Medici family, the most famous patrons of the 16th century. But Florence is not just a Renaissance showpiece: once you have had your fill of the historical trail there are many other things to see and do, including scouring the markets and chic boutiques or watching the world go by in the city's numerous café-bars or restaurants.
Day 7
Walk to picturesque San Gimignano with free time to explore; afternoon wine tasting.
After a short transfer to the quaint hamlet of San Donato, we walk through the farm grounds following the pathway to Montauto and on up to the picturesque mediaeval town of San Gimignano. The walk is not long and should take approximately 2 hours. The afternoon is spent exploring this beautiful town including visits to the Palazzo Comunale, Pinacoteca and Torre Grossa and there is some free time to wander and soak up the atmosphere. Before returning to the Villa, we enjoy a wine tasting in the nearby Villa Il Palagetto, where excellent Vernaccia wines are produced. Total walking approx. 10 km
Day 8
Fly to London
Transfer to Pisa; fly to London.
Prices & Availability
Chianti Walking and Wine Tour 5/5

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