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A Tuscan Harvest

Chianti, Castles and Tuscan Cooking

A relaxed walking holiday where we stay in two luxurious hotels - the first converted from a former Papal villa, the second an historic palace in the centre of a Tuscan village. One hotel has a pool and beautiful gardens, the other has a Spa.

This guided walking holiday in Tuscany brings you the best of central Tuscany. Experience superb guided hikes taking you off the beaten track. Visit Tuscan gardens and castles, drop in to wine estates, chat to the winemakers and taste their wines and olive oil. Enjoy delicious meals, accompanied by fabulous local wines, showcasing the wonderful fresh produce that is at the heart of Tuscan cooking. Have fun making fresh pasta with a celebrated local chef in the sixteenth century kitchen of a private country villa.  

The tour starts and ends in Pisa, Tuscany.  Many people choose to extend their walking holiday in Italy by visiting the Cinque Terre coast, Rome, Siena, Bologna or Florence.  For more details visit our City Guide page.  See more photos of this tour.

€2,795 per person
Single supplement:

Our tours are genuinely all-inclusive - learn more about what we offer. 

What's Included?
  • Experienced and knowledgeable guides who will look after your every need and bring this stunning area to life
  • 7 nights' accommodation in two fabulous hotels
  • All meals including wine.
  • Gourmet picnic lunches each day and snacks en route
  • Dinner in a variety of superb restaurants.
  • Museum visits and food/wine tastings as per itinerary
  • Support vehicle, enabling you to walk as little or as much of the trail as you please
  • Transport to/from Pisa in air-conditioned minibus
  • Comprehensive pre-trip information.
  • Luggage transported for you so all you need to carry is a small backpack with water etc.
Tour Dates
28th October 2016 - 4th November 2016

Day 1
Meet Pisa Airport at 1pm. Drive(2 hours) to La Suvera, our luxurious hotel converted from a former Papal villa, where we stay for 4 nights. Time to settle in and relax before we meet for a welcome drink in the gardens followed by a delicious dinner.

Day 2
Walk in the wooded hills of the "Montagnola". See the Renaissance gardens of Villa Cetinale and visit the beautiful garden and chapel at Celsa Castle. Picnic in the open countryside with views across to the towers of Siena. (16km/10miles). This evening we visit the pretty hilltop town of Casole d'Elsa near our hotel where we have dinner in a cosy trattoria.

Day 3
We depart the hotel on foot and follow former merchant trails up into the Montagnola hills, passing through ancient woodlands and coming upon an abandoned castle. Pass a small former quarry, once used for the lovely “pietra serena” stone typical of this area and descend to an pretty hamlet overlooking the valley of the River Elsa. Picnic in the open countryside before returning to the hotel. (8km/5 miles). Later in the day experience a Tuscan cookery lesson with a charismatic local chef in the 16th century kitchen of a nearby private villa.  Enjoy a relaxed evening with lots of opportunities for hands-on involvement!

Day 4
A leisurely start to the day before we drive to Siena and have time to explore this World Heritage city with a private tour of some of the lesser-known artistic gems. Enjoy a delicious lunch at a lively trattoria in the heart of the medieval city. Free time in the afternoon to shop and visit the sights before we return to our hotel. Casual pizza dinner in a nearby town.

Day 5
This morning we depart from La Suvera and drive to the heart of the Chianti Classico region. We visit one of the oldest churches in Chianti near the village of Panzano before walking through vineyards and woodlands to a local organic winery. Private tour of their cellars to taste their wines and olive oil before a picnic lunch on the estate. In the afternoon there is the opportunity to continue on foot to the market town of Greve-in-Chianti. (13km/8miles) We stay the next three nights at the four-star Palazzo Leopoldo in the hilltop village of Radda-in-Chianti. Dinner in the village this evening.

Day 6

Starting above the village of Radda-in-Chianti we climb up to the ridge of the Monte dei Chianti and the highest point in the region, Monte San Michele. From here we have views to the Arno valley and beyond to the Apennine mountains. Fabulous leisurely lunch at the renowned Ristoro di Lamole high in the Chianti hills before returning to our hotel. Time to relax before a light buffet dinner. (10km/6.3miles)  See our Blog for more on today's restaurant.

Day 7

Magnificent final walk in Tuscany in the more rugged region of Eastern Chianti. We pass through perfectly preserved villages en route to the magnificent Brolio Castle, owned by the Ricasoli family since the 11th century. Brolio Castle provides stunning views to Siena, the Tuscan Crete to the south and to the Chianti hills to the west. Visit the gardens and family chapel before a short drive back to Palazzo Leopoldo. Final dinner in a beautiful Radda restaurant. (16km/10.1miles)

Day 8
Return to Pisa Airport for 11am.

Extra Info

Shortest day: 8km/5miles
Longest day: 16km/10.1miles

There are 5 days of walking on the trip and one free day. In terms of terrain this is one of our more gentle itineraries. There are some long days of hiking, however, as on all tours there is always van support with the opportunity to walk a half-day and spend the afternoon at the hotel. We walk on strade bianche (gravel roads), through vineyards, along woodland tracks and quiet tarmac roads. This area of Tuscany is one of rolling hills with some significant ups and downs. Sturdy walking boots, with good ankle support, are recommended. Many guests like to hike with walking poles and these are very useful, especially on steeper sections and on the occasional stony or muddy descent.  To see how we grade the walking we have a simple comparison of all our tours taking into account ascents/descents, distances and terrain.

We have compiled a Reading List for ideas for books to enjoy on your walking tour.

Walking Gear
For helpful hints on what to wear, visit our Kit List page.

Buying Wine
We are often asked where guests can buy back home the wines tasted on the tours.  Our wine page has a few helpful pointers.


Spring and autumn are delightful times to walk in Tuscany. Warm, sunny days with cooler mornings and evenings.

May/September:Max 24°Min 15°Rainfall 55mm

Today's weather in Siena

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