A Tuscan Harvest

Chianti, Castles and Tuscan Cooking

This is a classic Tuscan tour with our itinerary 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. Dinner on the final evening is in the outstanding Arnolfo Ristorante – one of very few 2 Michelin-starred restaurants in Italy.

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. 

"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: €3,675 per person
Single supplement: €375

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, including Arnolfo Ristorante, with 2 Michelin stars
  • 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.

Your Health and Safety

See our new protocols to ensure the safety and wellbeing of both our guests and HH staff.

Tour Highlights

  • Beautiful hiking in classic Tuscan countryside
  • Visit to Siena with guided tour of artistic gems
  • Cooking class with delightful local chef and dinner in one of Italy's finest restaurants


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

Shortest/Longest Day: 8km/5miles: 14km/9miles

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.


Villa Le Barone: Historic family-owned villa in the heart of Chianti with lovely gardens and pool

Palazzo San Lorenzo: Four-star hotel with spa facilities, formerly a noble residence, in the medieval town of Colle Val d’Elsa

Tour Dates

28 September 2024 - 5 October 2024 27 September 2025 - 4 October 2025