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Guided Walking holiday in Tuscany, Italy

Italy • Tuscany • Val d’Orcia Walking Holiday

Brunello country - one of the joys of this walking holiday in Tuscany, ItalyPerfect walking holiday landscape in the Val d'Orcia, Tuscany, ItalyOur walks in Tuscany often follow footpaths lined by cypress treesA wooded walking location in the Val d'Orcia, Tuscany, ItalyA typical magnificent landscape on this guided walking holiday in Tuscany, ItalyWe pass beautiful farms as we walk through the Val d'Orcia,Tuscany, ItalyThe rolling landscape of Tuscany that we find on these walking holidays
Slide show with 7 images

Classic Tuscany 
A gorgeous walking holiday wandering through vineyards, past abbeys and zigzagging around hillsides of the Val d’Orcia in the heart of classic Tuscany. A dream location for this walking holiday in Tuscany

A typical itinerary on this walking holiday in Tuscany

Arrival day

Leaving Rome we arrive in medieval San Quirico d’Orcia in time for dinner.

San Quirico to Bagno Vignoni

A uniquely different day spent crossing the Crete Senesi – one of the most amazing landscapes in Italy. Walking in the near desert region has a gentle bleakness with occasional houses and lines of cypresses, the only signs of habitation

Ancient Sant’Antimo Abbey

From Montalcino, home of the famous Brunello wine, we walk an ancient route to the Abbey of Sant’Antimo. A day of olive groves and woodlands of oak and laurel.

Gelati in Buonconvento

After visiting a beautiful abbey, we pass through typical wine country with wonderful views and abandoned farmhouses before reaching ancient Buonconvento for a gelato.

Free day

Take a rest from walking and visit Siena, laze in the hotel gardens, relax by the pool or enjoy a spa treatment.

Monticchiello to Montepulciano

Leaving the small medieval hamlet of Monticchiello we find ourselves walking the dusty white tracks that snake their way through fields and forests to the ancient 5th century BC Etruscan town of Montepulciano.

Via vineyards to Pienza

Departing San Quirico, with its twisted medieval alleyways, we follow gentle footpaths through vineyards across the Renaissance new town of Pienza.

Departure day

We depart after breakfast for Rome airport.

Note: This is a selection of the many options available on this walking holiday in Tuscany, Italy. Weather conditions, group interests and the tutor will influence the final itinerary.

Where we stay on this walking holiday in Tuscany, Italy


Hotel Casanova

Our very comfortable and welcoming hotel just outside the walls of San Quirico D'Orcia offers en suite rooms, poolside views of countryside peace and quiet and a wide choice of typical Tuscan cuisine and wines.The hotel offers a wonderful, newly refurbished spa with pool, jacuzzi, sauna and beauty treatments. All rooms have air conditioning, TV, internet access, telephones and minibar. The perfect base for a walking holiday in Tuscany.
Bedroom in Hotel Casanova, a very comfortable base for our walking holidays in Tuscany, Italy Lounge in Hotel Casanova, a very comfortable base for our walking holidays in Tuscany, Italy
Swimming pool at Hotel Casanova, a very comfortable base for our walking holidays in Tuscany, Italy
Newly renovated spa in Hotel Casanova, a very comfortable base for our walking holidays in Tuscany, Italy Relax at the newly renovated spa in Hotel Casanova, a very comfortable base for our walking holidays in Tuscany, Italy
Airport transfer time
Approximately 2¼ hours
Dates and prices
We don’t have any planned dates for this location, but if you would like to be kept updated, why not register your interest now! Alternatively, have you considered one of our other fabulous locations?
If you would like to travel as a private group, dates can be arranged at any time to suit you. Please contact us.
What's included
5 full days of walking with professional local guide
7 nights in en-suite accommodation
5 lunches and 6 dinners with wine
All transfers and transport
Free use of spa facilities
Personal welcome at Rome airport
Visits to Montepulciano, Pienza and Montalcino
Visit vineyard and wine tasting
Gregorian Monks chanting in Sant’Antimo Abbey
Where we stay
Getting there
Underfoot
Mostly white tracks and footpaths.

Guided walking holidays

Best field staff
Tour managers with superb local knowledge ensure insider access
Talented, considerate and well-respected tutors
Highly experienced and entertaining walking guides
Best office team
We know the locations, tutors and local guides
We are polite, friendly and always here to help
Our hotels are all chosen by our trusted and experienced staff
Talk to us
Speak to a Specialist
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We’re here Monday to Friday 09:00 – 17:00
Save money
Choose a single supplement-free holiday
Bring a non-participant partner or friend
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