Holidays to Tuscany and Italy: Hiking Holidays > A Tuscan Harvest

Click an image to enlarge and for <slide show>
A Tuscan Harvest
A Tuscan Harvest
A Tuscan Harvest
A Tuscan Harvest
A Tuscan Harvest

A Tuscan Harvest

A Tuscan Harvest – 8 Days 

Chianti, Castles and Tuscan Cooking 

A relaxed walking holiday where we stay in two beautiful 

and luxurious hotels in the heart of Tuscany. Borgo Pretale 

is a 4-star hotel converted from a remote medieval village in 

an idyllic, peaceful location near Siena. The hotel has a pool 

and beautiful garden. 

Palazzo Leopoldo is a former manor house situated in the small yet vibrant village of Radda-in-Chianti. The 

hotel has a Spa. 

This guided walking holiday 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. Private cooking demonstration at a historic villa with a local chef. 

What is included? 

• 7 nights’ accommodation in two 4 star hotels 

• Two experienced and knowledgeable guides who will look after your every need and bring this stunning area to life 

• All meals including wine. 

• Gourmet picnic lunches each day and snacks en route 

• Dinner in a variety of superb restaurants. 

• All Museum visits and 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. 


Day 1 

Meet Pisa Airport at 1pm. Drive (2 hours) to Borgo Pretale, our hotel converted from a Medieval hamlet, 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, past the 

Renaissance gardens of Villa Cetinale and the beautiful garden 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. 

Day 3 

Beautiful walk through the hills near Siena, discovering some the 

evocative churches and abbeys hidden in the woods which tell of a time when the trails were busy with merchants and pilgrims. Picnic in the open countryside. (9km/5.7miles). Later in the day experience a cookery demonstration of Tuscan cuisine with a private chef at a nearby country house, with plenty of opportunity for hands-on involvement. 

Day 4 

After a relaxed start to the day, we drive to Siena and have time to explore this beautiful medieval gem of a city. Discover some of the lesser-known artistic gems and enjoy a fabulous lunch at a lively trattoria in the heart of the city. Time to relax by the pool in the afternoon before a light dinner in the hotel. 

Day 5 

We depart Borgo Pretale and drive to the heart of the Chianti Classico region. Visit one of the oldest churches in Chianti near the village of Panzano in Chianti before walking through vineyards and woodlands to a local organic farm. Private tour of their cellars to taste their wines and olive oil before a picnic lunch on the estate. In the afternoon, opportunity to continue on foot to the market town of Greve-in-Chianti. We stay the next 3 nights at four star Palazzo Leopoldo in the village of Radda-in-Chianti. Dinner in Radda this evening. (13km/8.3miles) 

Day 6 

Starting above the village of Radda-in-Chianti we climb up to the ridge of Monti dei Chianti and the highest point in the region, Monte San Michele. From here you have views to the Arno valley and beyond to the ridge of the Appenine Mountains. Fabulous leisurely lunch at the renowned Ristorante Lamole high in the Chianti hills before returning to our hotel. Time to relax before a light dinner. (10km/6.3miles) 

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 returning to our hotel for a memorable last night 

dinner. (16km/10miles) 

Day 8 

Return to Pisa Airport for 11 o’clock. 


Shortest day: 9km; 

Longest day: 16km 

There are 5 days of walking on the trip.We walk on strade bianche (gravel roads), through vineyards, along woodland tracks and quiet tarmac roads. There is always van support with the opportunity to walk a half-day and spend the afternoon at the hotel. This area of Tuscany is one of rolling hills with some significant ups and downs. 

Sturdy walking boots, with good ankle support, are recommended. 

Walking poles would be an advantage, especially on steeper sections. 


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

Sept: Max 24° Min 18°. Rainfall 55mm 

Dates: 21st - 28th September 2014 Fully booked!

Cost: £2146.00 per person Single supplement £180.00