A Tuscan Harvest
Chianti, Castles and Tuscan Cooking
Tour Dates
27 September 2025 – 4 October 2025
Tour Cost
€3,675 per person
Single supplement: €375
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.
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.
Our tours are genuinely all-inclusive – learn more about what we offer.
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
Walking/Terrain
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.
Accommodation
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
Itinerary
LEAVE BLANK
Day 1
We meet at Pisa Centrale Train Station at 10am. Our first stop is in the village of Passignano with its medieval abbey nestled amongst the vines. After a tour of the abbey we enjoy a delicious lunch in a local Osteria. In the afternoon we continue our drive through Chianti to our beautiful hotel just outside the town of Panzano, where we stay for 4 nights. Time to settle in and perhaps have a dip in the pool before enjoying a welcome drink in the garden and dinner in the hotel.
Day 2
We walk into Panzano and experience its small weekly market and delightful shops, including the now famous Chianti Butcher – Dario Cecchini. From the village we follow quiet country lanes and farm trails with panoramic views of northern Chianti. We picnic in the countryside by a remote chapel. In the afternoon a short walk brings us back to the hotel. Later in the day we drive to the lively town of Greve-in-Chianti. There is time to visit the renowned wine cellars and browse the shops before dinner in a local restaurant.
(8km/5miles)
Day 3
We head out from the hotel on foot. Firstly we enjoy expansive views over stunning scenery before following a quiet trail through the woods, climbing gently to a small hamlet. We visit a boutique wine producer for a private tasting before a leisurely lunch at the renowned Ristorante Lamole, high in the Chianti hills. We return to the hotel by minibus and there is time to relax in the gardens. In the evening we stroll to a charming church nearby with magnificent views over the vineyards bathed in the evening sunshine. After our long, lazy lunch we enjoy a light evening picnic as the sun is setting.
(8.5km/5.2 miles)
Day 4
We head out on foot from the hotel. Our trail leads across rolling hills from castle to castle, passing through vineyards and olive groves with far-reaching views towards Florence and the Apennine mountains. We picnic near a fortified village overlooking the countryside before continuing along an ancient trail through the woods to arrive at the imposing castle of Verrazzano. We visit the gardens and wine cellars and enjoy a glass of wine before returning to our hotel. Dinner in the hotel restaurant.
(14 km/9 miles)
Day 5
We depart Villa Le Barone after breakfast and drive to Siena. We explore this World Heritage city with a tour of some of the lesser-known artistic gems and enjoy a delicious lunch at a lively trattoria. Free time in the afternoon to shop and visit the sights before we head to Colle Val d’Elsa. We check in to the four-star Palazzo San Lorenzo in the old part of town where we stay for 3 nights. Dinner in a local restaurant this evening in Colle.
Day 6
A beautiful walk through pretty farmland takes us past some lovely villas and farmhouses with fabulous views to San Gimignano and beyond. We picnic in the gardens of a private villa before returning to the hotel. Later in the day we drive to a charming country villa to enjoy a fabulous hands-on cooking class with a local chef. We taste some local wines from the Chianti Colli Senesi and dine on the fruits of our labour.
(10km/6.2miles)
Day 7
Our final hike follows a section of the famous medieval pilgrim route the Via Francigena. We hike from the fortified village of Monteriggioni towards Colle Val d’Elsa, passing vestiges of castles and abbeys as we travel through history on foot. Picnic in the countryside before heading to a local gelateria for the best ice cream in the region and maybe a coffee too! In the afternoon there is time to explore the beautiful medieval town of Colle Val d’Elsa with its craft shops and glass workshops. Our final dinner is at the magnificent Arnolfo Ristorante, one of very few restaurants in Italy with two Michelin Stars.
(10km/6.2miles)
Day 8
We return to Pisa Centrale Train Station for 11 am.
