Walking Holidays in Tuscany

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Spring and Autumn
The best of the Val d’Orcia - a UNESCO World Heritage treasure
7 Nights
Luxuriate in gorgeous landscapes, rich history and fabulous cuisine on a Tuscany walking holiday in the Val d’Orcia, a UNESCO World Heritage treasure.

On this trip we bring you the best hillwalking in Tuscany. Spend your days amidst cypress trees, vineyards and olive groves, whilst venturing into exquisite hilltop villages steeped in medieval and Renaissance history. Set against an idyllic backdrop of rolling hills, this holiday showcases the infinite variety of a world-celebrated destination for walkers and culture seekers.Each day, you choose a longer rambling hike or a shorter, more leisurely walk, setting off each morning with comprehensive route notes and maps that will guarantee you a succession of enchanting days out.

A walking holiday in Tuscany is almost too good to be true – and certainly a ‘must’ for every walker’s bucket list. Travel writers wax lyrical about the unassuming abundance of masterpiece art, architecture, culture and gastronomy in a region famed for its red wines. It’s all here: dreamy landscapes of terracotta farmhouses, ancient villages and gentle hills are linked by a network of walking trails called Strade bianche. Our local towns are among the most alluring in Europe, whilst further afield historic giants, notably Siena and Florence, can easily be included in a wider itinerary.

In its classically Tuscan location, our accommodation at Il Rigo will enchant you. Two beautifully converted country houses on a working farm combine to provide a  uniquely charming springboard for your days out. Owned by an award-winning Italian cook, expect to eat and drink supremely well over sociable dinners with like-minded guests. And prior to dinner, join us for an aperitif, an opportunity to chat with other guests and glean information to plan your days. Either way, your evenings will be the perfect conclusion to a memorable day in glorious surroundings.

At a glance


Spring 2024
23 – 30 March
30 March – 6 April
6 – 13 April
13 – 20 April
20 – 27 April

Autumn 2024
21-28 September
28 September – 5 October
5 – 12 October
12 – 19 October
19 – 26 October


Single Supplement – £195


On this holiday you have a choice of two walks each day, one longer than the other. Depending on the walks you choose, expect to walk for 3 to 7 hours each day with between 320-600m of ascent.

Office Hour

This is a popular feature of our Tuscany holidays. Each early evening (except Wednesday) join us in Il Rigo’s vine-covered courtyard for an informal and relaxed pre-dinner drink. We can answer any questions you might have about your Walk Pack, and help you to choose and/or plan your next day’s walk. Alternatively, simply drop by for a drink with us and other guests before dinner.

What’s Included

Airport Transfers – between Pisa Airport/Siena Rail Station & Agriturismo Il Rigo. 
7 Nights Half Board
– at Agriturismo Il Rigo (bed, breakfast and 3-course dinner with wine).
Walk Pack Collett’s holidays are all about memorable walks!  Your pack contains comprehensive route notes and maps for trouble-free self-guiding at your own pace on all our featured walks, each one a tried and tested gem.
Collett’s Walk Team – we are here to support you with all things walks-related and ensure you get the very best out of your stay.
Transport to/from trailheads – on three of the five walk days (with return transport as necessary) as stated in the Itinerary.
Local Wine Tasting – try some world-celebrated local wines before dinner on the Thursday of your stay.

Not included – packed lunches, available to purchase at Il Rigo.


This holiday is based at Agriturismo Il Rigo near San Quirico in the Val d’Orcia. The best option for this holiday is to fly in and out of Pisa Airport

Airport Transfers – from Pisa Airport (3hrs) and Siena Rail Station (1hr) are included.
These depart Pisa Airport at 1500 (your flight must land before 1430) and we aim to pick up in Siena at 1700. Expect an early start on your departure day as the return transfer will leave Il Rigo at 6am (your flight home from Pisa must depart after 1100). 

Private Airport Transfers – available at a supplement, are ideal if you’re travelling in a group and/or plan to arrive into another airport such as Rome or Florence – please contact us for a quote.

Fly-driving – this option suits guests who would prefer complete flexibility throughout their stay (especially on their arrival and departure days, and the mid week rest day).


This trip is ideal for parties with varying levels of fitness, as you can do different walks and still enjoy the same holiday. We’ve designed a special itinerary made up of two walks each day: one easier route, and one that’s harder or longer. On this trip, people of similar fitness levels soon get to know each other and walk together, though of course those who prefer to walk independently can venture out on their own. We want you to explore this paradise just as you wish!


Sat - Arrive

Arrive in the Val d’Orcia, with its rolling wheat fields and luscious vineyards. You’ll stay in the heart of the Tuscan countryside, nestled between the villages of San Quirico and Pienza. Upon arrival, you’ll be warmly welcomed at the wonderful Agriturismo Il Rigo by the owners Mathias and Luisa, and our Walks Team.


Sun - Pienza & Capella Vitaleta

Choose between :

Easy/Moderate version: 12.5 km, 3 – 5 hours walking, 310m ascent
The opening walk of the trip is a lovely route that takes in some of the iconic sights of the Val D’Orcia, including the UNESCO World Heritage town of Pienza. Arriving in this medieval hilltop town for lunch, gives you ample time to explore this historic hilltop town before enjoying the rolling hills of the Val d’Orcia on the way home.

Moderate/Hard version: 14 km, 4 – 6 hours walking, 440m ascent
An early morning extension takes you via Capella Vitaleta and the ever photogenic Podere Belvedere before reaching Pienza.


Mon - Fortified Hamlets & Historic Spa's

Choose between :

Easier Option: 13.5 km, 4 – 5 hours walking, 340m ascent
On today’s shorter option, you’ll walk through the olive groves and Vineyards that surround San Quirco before reaching an old Medici stronghold in the hamlet of Vignoni Alto.  

Harder/Longer Option: 18 km, 5 – 6 hours walking, 304m ascent
The longer of the two walks today visits one the the most iconic sights in Tuscany, the historic hamlet of Bagno Vignoni, famous for its hot springs. With sweeping views across the valley the walk returns to Il Rigo in the early afternoon. 

tuscany-hillwalking-holidays-montalcino (4)

Tue - The Majestic Montalcino

Moderate Walk: 15.5 km, 4 – 6hours walking, 510m ascent
Leaving from Agriturismo Il Rigo, this walk follows the ancient Via Francinega pilgramage path as you meander through the Brunello Vineyards that surround the wonderful hilltop town of Montalcino.

Today a short transfer (included) will collect your from Montalcino at the end of the day.



Wed - Rest Day

Your rest day is the perfect opportunity to do something different – such as visit Siena, treat yourself to a spa in Bagno Vignoni, or book yourself onto a cookery class to remember….

A fantastic option for your mid-week rest day

Lorenza, the mother of Il Rigo, is an award winning Tuscan chef and she offers traditional Tuscan cookery classes from her family home in the centre of San Quirico d’Orcia. She just requires at least 48 hours notice in order to ensure fresh ingredients and a minimum group size of 4. The class starts at 10:45am at a price of €70 per person. Wine is available but not included in the price of the class.

With Lorenza’s expert guidance you will prepare together a four-course menu, including the preparation of hand made fresh pasta. Recipes change according to the season, but they are always traditional and Tuscan. Aprons are provided, as is water, coffee, an aperitif and a small appetizer, before the group sits at the table and enjoys the fruits of its labour over a four course lunch.


Thur - The rolling Val d'Orica countryside. Evening Wine tasting

Choose between :

Easier Option: 11.5 km, 3 – 4 hours walking, 206m ascent
A lovely walk through the rolling countryside so synonymous with the Val d’Orcia. Extended views acroos to Montalcino and Montepulciano await along with those across to the northern Crete Senesei region.

Harder/Longer Option: 17 km, 5 – 7 hours walking, 351m ascent
The longer walk of the day extends the morning’s route to incorporate the iconic Cipressi, a ring of Cypress trees set amidst the wheat fields.

As Tuscany, and more importantly the Val d’Orcia, is home to some of the world’s best wines, we organise a wine tasting this evening before dinner (included).


Fri - Monticchiello & Montepulciano

Choose between :

Easier Option: 9.2 km, 3 – 4 hours walking, 320m ascent
Starting at the wonderful village of Montichiello, todays shorter walk reaches approaches Montepulciano through the famous Vino Nobile vineyards before arriving in the iconic hilltop town just after lunch.  

Today a short transfer (included) will take you to Montichiello in the morning.

Harder/Longer Option: 15.5 km, 4 – 6 hours walking, 530m ascent
Starting in Pienza the walk today passes through the wonderful walled village of Montichiello before passing through the vineyards from which the famous Vino Nobile di Montepulciano wine is made. The walk ends by passing the San Biaggio Cathedral and climbing through the historic street of Montepulciano. 

Today a short transfer (included) will take you to Pienza in the morning.


Sat - Departure

Our transfer service generally departs very early, at around 6am – in order to reach Pisa Airport in time for mid morning return flights.

Need to Knows

Transport to/from trailheads: Some of our walks start from (and end at) Il Rigo. However, where transport is required at either end of a walk, this is arranged by us as per the itinerary and is included in the price of your holiday. Il Rigo is quite rural, 25 minutes on foot from the small town of San Quirico. Consider having a car at your disposal if you want to fit in around your walks, visits to local places of interest.

Booking Conditions – be sure to read our full terms and conditions here before booking.

At Your Own Risk – please read the important notes here.

Travel Advice – check your government’s travel advisory for up-to-date information and advice about your destination. For UK citizens, check the latest Foreign, Commonwealth & Development Office advice here.

Passport & Visa –  any questions should be directed to the relevant embassy of your destination country; find out more here. It is your responsibility to be in possession of a full passport, valid for your chosen destination.

Travel Insurance – having adequate and valid travel insurance is a condition of booking with us. Details of our insurance partner, Campbell Irvine, are here.

Health Information – You should carry either an European Health Insurance Card (EHIC) or a Global Health Insurance Card (GHIC)  Neither is an alternative to adequate travel insurance. For more information visit https://www.gov.uk/foreign-travel-advice and https://travelhealthpro.org.uk/

ABTA – Independent travel advice and help is always available from ABTA by calling 020 3117 0599 or visiting www.abta.com.

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