Walking Holidays in Italy - Tuscany - Short Break Walks

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Our Tuscany Short Break begins in the stunning capital city of the region, Florence, regarded by many as the birthplace of Renaissance. You stroll through vineyards where the world-famous Chianti wines are produced before arriving at the historic town of Impruneta. More vineyards await you with opportunities to sample these delicious wines before you arrive at the scenic village of Chiocchio.

The Area

Beauty, relaxation, history and wine! This perfectly describes the mesmerising heart of the Chianti wine-growing area. You will be walking through vineyards where the world-famous Chianti wines are produced, you will also be able to enjoy plenty of these along the way. It is from this area alone that Chianti can boast its black-rooster seal, “gallo nero”. You will also be able to indulge in the delicious food and olive oils of the Tuscan region. 

Day 1: You will be collected from Florence airport and transferred to your first hotel in Florence. Overnight Florence.

Day 2: Begin in the outskirts of Florence. Pass Renaissance villas and traditional villages, until you reach hills peppered with cypresses, olive groves, vineyards, villas and hilltop hamlets, and later a serene wooded valley. Overnight Impruneta.

Ascent: 445m (+70m from centre of Florence). Descent: 290m. Distance: 11 ¼ miles (from centre of Florence), 9 ½ miles (from the outskirts). Time: 6 hours (from centre of Florence), 5 hours (from the outskirts). 

Day 3: Start the day in the wide piazza at the heart of Impruneta. Wander through beautiful vineyards and olive groves until you descend to the small town of Ferrone. From Ferrone, follow a long gradual ascent to the Poggio al Mandorli, continue towards Chiocchio. Overnight Chiocchio.

Ascent: 340m. Descent: 315m. Distance: 6 ½ miles. Time: 5 hours.

Day 4: You will be collected from your last hotel in Chiocchio and transferred back to Florence airport.

Extra Nights

Why not add an extra night or two in Siena? This stunning World Heritage Site city is well worth exploring.

Price in GBP£ Price in USD$

Tuscany – Short Break Walks



Not Included


3 night’s accommodation



Lunches & drinks with meals


3 breakfasts



Travel Insurance (required)


2 dinners





Private car transfers between Florence airport and first/last hotels





Additional people transfer’s as indicated in itinerary





Baggage transfers between hotels (1 bag per person @20kg)





Route notes & walking map




Optional Extras





‘With flights’ includes typical flight prices between London and Florence. Flights from many local airports are also available (exact prices for your dates are available on request)

All prices valid for 2020/21 - Prices are per person in GBP / UK £


With Flights

Without Flights

Extra Night

Single Supplement* per night

01 Apr – 21 Apr

01 Oct – 17 Oct





22 Apr – 30 Sep





18 Oct – 31 Oct





*If at least two travelling. Please call to discuss availability and transfer supplements for one person travelling alone.

POA – Prices upon application

Extra nights in Siena (based on two people in a shared twin/double room including breakfast):

    4* hotel in Siena for £65 per person


Price in GBP£ Price in USD$

Hotel Park Palace 4*, Florence

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This is a real Florentine-style villa near the Boboli Gardens and Ponte Vecchio on the opposite side of the river to central Florence. The hotel is surrounded by a magnificent garden in which there is a swimming pool with lounge chairs and beds. The historical centre of Florence is only a 20 minutes’ walk away where one can visit all of the most famous monuments like the Duomo, Palazzo Pitti, and the Uffizi.

All rooms feature free Wi-Fi, television, telephone, safe, air conditioning and private bathroom with WC, shower/bath and hairdryer.


Hotel Bellavista 3*, Impruneta

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This family hotel is now being run by its 4th generation since it opened in 1906. It is renowned for its warm, welcoming hospitality, which makes you feel at home in a typical antiquated Tuscan environment with all of the modern-day comforts. The hotel is situated in the main square at Impruneta near the basilica of Santa Maria. The popular restaurant, serving traditional Tuscan food and its own wines, is on the top floor and you can eat outside in the summer, with the “bella vista” ahead of you.

All rooms feature free Wi-Fi, television, telephone, safe, air conditioning and private bathroom with WC, shower/bath and hairdryer. 


Locanda Il Gallo, Chiocchio

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This charming hotel & restaurant had an authentic Italian feel in each room. It is very comfortable and is set in a great location for walkers. Their restaurant offers a wide choice of delicious dishes, all made the traditional way – very inviting after a long day’s walking!

All rooms feature free Wi-Fi, television, telephone, air conditioning, minibar and private bathroom with WC, shower/bath and hairdryer. 


Availability Information

The trek is available from April to October. The best time to visit Tuscany is from April to June and from September to October when weather is usually good, it is not at its hottest and there are fewer tourists. 

Please note our best to go information is generally referring to the walking which may fall in the early or late season in some places. This may mean that not all tourist facilities will be open at the time you visit.  

When to book your walking holiday in Italy - Tuscany - Short Break Walks

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