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Your walking holiday in Italy

Wine Trails of Classic Tuscany | Guided Group

Total Distance 26 miles (41km) | Average distance per day 6 miles (10km)

Embark on a great Italian journey over rolling hills, through medieval villages, and into bustling cities. Enjoy stretching your legs in the sun, testing delicious food and wine and discovering some of Italy’s best culture and history. You will spend your holiday wandering the Chianti vineyards and the iconic Tuscan landscape. You will also explore historic Montalcino and Montepulciano, take in the sights of marvellous Siena and soak up the atmosphere of Renaissance Florence.

What not to miss

  • Tuscan landscapes
  • Wine tastings
  • Hills
  • Siena and Florence
  • Local cuisine

What’s included

  • Meals (breakfasts, 2 lunches)
  • Transfers (minibus, train)
  • 4 nights standard hotels, 3 nights standard guesthouse
  • Airport transfers
Your walking holiday in Italy

Wine Trails of Classic Tuscany | Guided Group

Day 1

Arrival in Pisa.

You will begin your adventure in Pisa where we will meet up and then make our way to Castellina in Chianti, a country town with Etruscan and Roman origins. The first accommodation is located in a region known for its wine.

Day 2

Round Tour Chianti country | Distance 4 miles (7km) | Elevation +/- 150m.

Your first walk will begin at the chapel of Santa Maria, close to the town of Volpaia. This walk takes you through vineyards and up the Chianti hills to the beautiful village of Volpaia. You will continue the walk through the Tuscan countryside before descending back into Santa Maria Novella for your picnic lunch. In the afternoon we will take a bus to Radda where you will have time to walk around before heading to Rocca della Macie for our wine tasting of the iconic Chianti Classico.

Meals included: breakfast, lunch

Day 3

Round San Gimignano | Distance 6 miles (10km).

Today’s walk will take you along the famous ancient pilgrimage path of the Via Francigena (which stretches from Canterbury to Rome). You will set off from the medieval town of San Gimignano where you may be able to stop the town’s thirteen medieval towers after setting off. You will then have time to explore the beautifully-preserved medieval trade town and relax, walk up to the Torre Grossa, or visit the Duomo after lunch.

After lunch we plan to visit the Sovestro winery for a tasting of some of the local San Gimignano white wine. We then continue to Monteriggioni, a beautifully preserved fortified hill-top village, where we can walk around the walls before driving back to Castellina later this afternoon.

Meals included: breakfast

Day 4

From Castellina to Pienza.

Today we will travel to the beautiful city of Siena. Here you will have the chance to discover the incredible history of this town such as how it was once Florence’s rival in terms of trade. You will get to walk around the city and visit the market, the central square, Il Campo, and the beautiful Duomo (cathedral) or the impressive Piazza del Campo. After spending the day here, we will head to the town of Pienza in southern Tuscany. Pienza, our base for the next three nights, is a Renaissance town and, in 1996, was declared a UNESCO World Heritage Site.

Meals included: breakfast

Day 5

Round Tour Montepulciano | Distance 7 miles (12km) | Elevation +/-350m.

We will leave in the morning from Pienze, for our fifth day’s walk. We will walk to the village of Montichiello, but not before walking along the traditional ‘strade bianche’ and along one of the most admired cypress tree avenues in Tuscany. Once at Montichiello, we will have our well-earned lunch and rest a little before heading for the world-famous temple of San Biagio. After visiting the 16th century church, we will head to Montepulciano which is renowned for its fantastic food and wine. If time allows, we will explore some of the town’s underground cellars, and taste the traditional wine, before heading back to Pienza by local bus.

Meals included: breakfast

Day 6

Round Tour Montalcino | Distance 7 miles (12km) | Elevation +/- 450m.

On your penultimate day, we will drive to San Quirico D'Orcia, a beautiful town that lies along the Via Francigena pilgrimage route. After strolling through the town, we will make our way downhill and cross the Asso river, as the while you will have stunning views over the vineyards and hills and maybe even the towers of Siena, which are sometimes visible on the horizon. Our final destination is the hill-top town of Montalcino. We have some free time to explore and the chance to enjoy a wine tasting of the famous Brunello di Montalcino wine before heading back to our accommodation.

Meals included: breakfast, lunch

Day 7

From Pienza to Florence.

On the last day, we will leave Pienze for the wonderful city of Florence. The spiritual home of the Renaissance, Florence is considered by many to be one of the most beautiful cities in Italy. Upon arrival, you will get a guided tour of the city, before being free to see whatever tickles your fancy. You may want to see the Ponte Vecchio, the oldest and most famous bridge in Florence and the only one that was not demolished during the German retreat of 1944, or the Cathedral of Santa Maria del Fiore with its giant dome that dominates the city skyline. Early evening is the perfect time to walk up to the Piazzale Michaelangelo for a great view over the city.

Meals included: breakfast

Day 8

End in Pisa.

We say “arrivederci” and “a presto”!

Meals included: breakfast

This tour is operated by our preferred local partner.

Your walking holiday in Italy

Wine Trails of Classic Tuscany | Guided Group

Your walking holiday in Italy

Wine Trails of Classic Tuscany | Guided Group

Note: The accommodation listed below is indicative, it is not guaranteed and is subject to availability. Alternative accommodation of an equal standard may be used.

Villa Cristina, Castellina

Ideally located at a five minute-walk from the heart of the town of Castellina, this cosy hotel offers an outdoor swimming pool and a garden.

Hotel San Gregorio, Pienza

3-star

The Hotel Residence San Gregorio, surrounded by a garden with swimming pool, offers classic style spacious suites and a restaurant serving delicious food.

Classic Hotel Florence, Florence

3-star

This beautiful 19th Century refurbished villa offers elegant rooms with antique furnishing. It is ideally located and surrounded by quite gardens.

Your walking holiday in Italy

Wine Trails of Classic Tuscany | Guided Group

Package Prices 2019 (Flights and Transfers Included)

2019 Departure Dates Nights Adult Price  
21 April – 28 April  7 £1,199 Enquire now
12 May – 19 May  7 £1,199 Enquire now
02 June - 09 June  7 £1,199 Enquire now
08 September – 15 September  7 £1,245 Enquire now
22 September – 29 September  7 £1,215 Enquire now
06 October – 13 October  7 £1,199 Enquire now

Package prices are indicative, please contact one of our Activities Experts for more information.

Tour Only Prices 2019

2019 Departure Dates Nights Adult Price  
21 April – 28 April  7 £975 Enquire now
12 May – 19 May  7 £975 Enquire now
02 June - 09 June  7 £975 Enquire now
08 September – 15 September  7 £975 Enquire now
22 September – 29 September  7 £975 Enquire now
06 October – 13 October  7 £975 Enquire now

Extras

Single room supplement: from £250

Solo travellers

On this tour we do not require you to pay a surcharge for travelling alone. We will arrange for you to share accommodation with another traveller of the same gender and if we cannot match you up we will provide a single room at no extra charge. If you prefer not to share a single supplement is payable to guarantee your own room. The cost of the single supplement is listed above.

Your walking holiday in Italy

Wine Trails of Classic Tuscany | Guided Group

Total Distance

26 miles (41km)

Average distance per day

6 miles (10km)

Suitability

Walks on 4 days for between 3.5 to 5 hours. You will be walking on a mix of 'strade bianche', compacted gravel roads typical of Tuscany, as well as farm trails and mule tracks on undulating hilly terrain. 

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