A Tuscan Harvest

Chianti, Castles and Tuscan Cooking

This is classic Tuscany with the tour celebrating the region's unmistakable landscape, abundant vineyards and strong culinary heritage.  The hikes take us off the beaten track to remote castles, formal gardens and the vineyards of Chianti where we meet local winemakers to taste their wines and olive oils.   A free day in Siena offers the chance to explore this medieval jewel and see the Piazza del Campo where the legendary Palio horse-race is run twice each year.  We have fun with a local chef making our own pasta in the sixteenth century kitchen of a private country villa.  We get to enjoy a variety of fabulous restaurants along the way which showcase the very best of Tuscan cooking and the region's world-famous wines.

The tour starts and ends in Pisa, and our pick-up and drop-off points are Pisa Centrale train station and Pisa airport. 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. The next departure of this tour will be 25th September - 2nd October 2021, and we will have a new-look itinerary which will be published shortly.

"Our holiday in Tuscany was absolutely amazing, and you took great care of us. We loved never having to make a decision regarding accommodation, food or wine. Thank you from the bottom of our hearts for the great memories." Norma Likely


Cost: €2,995 per person
Single supplement: €325

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 Highlights

  • Cooking class with delightful local chef
  • Beautiful hiking in classic Tuscan countryside
  • Visit to Siena with private guided tour


Mostly gentle walking on gravel roads and farm trails. Rolling hills so lots of up and down but no major climbs.

Shortest/Longest Day: 9km/5.7miles: 16km/10.1miles

We have graded this hike a Level 2. Some of our tours are more challenging than others, so see how we grade our hikes to make sure you choose the right one for you. If you are interested in this tour then you might also like to take a look at The Jewels of Piedmont.


La Bagnaia: A medieval estate which has preserved its character and history in the heart of the Tuscan countryside

Palazzo Leopoldo: Four star hotel, formerly a noble residence, in the delightful centre of Radda-in-Chianti

Tour Dates

25 September 2021 - 2 October 2021