Tuscany Walking Holiday

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Spring and Autumn
The best of the Val d’Orcia - a UNESCO World Heritage treasure
7 Nights
Indulge in Tuscany's beauty, history and cuisine on a Val d’Orcia walking holiday, a UNESCO World Heritage site.

Explore hilltop villages surrounded by cypress trees, vineyards, and olive groves against the backdrop of rolling Tuscan hills. Each day offers a choice between longer hikes or leisurely walks with detailed route notes and maps, and our Walks Team are there to help you find the right routes for your needs throughout your holiday.

Tuscany’s allure lies in its art, architecture, culture, and renowned red wines. Experience dreamy landscapes, ancient villages, and gentle hills connected by walking trails. Stay at Il Rigo, a charming family run farmhouse. Owned by an award-winning Italian cook, this Tuscan walking holiday alos offers delightful dinners and sociable evenings. With nearby historic towns like Siena and Florence, this trip promises an unforgettable experience.

Take a look through this page for everything you need to know about this amazing walking holiday in Tuscany, and when you’re ready, click the ‘Enquire’ or ‘Book Now’ buttons, complete the information and let our skilled enquiry team help you make this holiday a reality.

At a glance


Spring 2024
6 – 13 April – Sold out
13 – 20 April – Sold out
20 – 27 April – Sold out

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 Sunday 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

Example Flights:
London Stansted
London Heathrow
London Gatwick

Airport Transfers on Saturdays – 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 1130). 

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).


Each day you have the choice of two walks, one longer than the other, making it the perfect holiday for couples who like to vary their walks and also for small groups made up of people with different levels of fitness. On this trip, like-minded walkers soon get to know each other and often team up to walk together. Others choose to venture out independently on their own. Whatever you do, we want you to explore this paradise just as you wish!


Sat - Arrive

Arrive in the Val d’Orcia, with its rolling wheatfields and luscious vineyards. You’ll stay in the heart of the Tuscan countryside, nestled between the villages of San Quirico and Pienza. On arrival, you’ll be warmly welcomed at the enchanting Agriturismo Il Rigo by our own Walks Team and your hosts, Matthias and Luisa, who own Il Rigo and the surrounding land.


Sun - Pienza & Capella Vitaleta

Choose between :

Easy/Moderate Option: 12.5 km, 3 – 5 hours walking, 310m ascent
The opening walk of the trip is a delight that takes in one of the most iconic sights of the Val D’Orcia, namely the UNESCO World Heritage town of Pienza. Arriving in this exquisite medieval hill-top town in time for lunch gives you ample time to explore its historic and architectural treasures in the early afternoon, before marvelling at the rolling hills of the Val d’Orcia on the way home.

Moderate/Hard Option: 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.
Winetasting: as Tuscany, and more importantly the Val d’Orcia, is home to some of the world’s best wines, join us for a complimentary winetasting before dinner this evening.


Mon - Fortified Hamlets & Historic Spas

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 Quirico 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 most iconic sights in Tuscany, the historic hamlet of Bagno Vignoni, famous for its hot springs. Sweeping valley views characterise the walk back 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

This walk follows the renowned ancient pilgrimage trail, known as the Via Francinega. Your destination is magical Montalcino, surrounded by the Brunello vineyards that produce one of the most celebrated red wines in the world.

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….

Lorenza is Luisa’s mother the matriarch at Il Rigo and Luisa’s mother. She is also an award- winning chef. She offers traditional Tuscan cookery classes from her family home in the centre of San Quirico d’Orcia. With her 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. Subject to availability (and first-come, first-served), Lorenza requires at least 48 hours notice in order to ensure fresh ingredients. Maximum group size is 4. The class starts at 10.45 and costs €70 per person. Wine is available but not included in the price.


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

Choose between :

Easier Option: 11.5 km, 3 – 4 hours walking, 206m ascent
A charming walk through countryside so synonymous with Tuscany and the Val d’Orcia. Enjoy extended views to Montalcino and Montepulciano and also the northern Crete Senesei region.

Harder/Longer Option: 17 km, 5 – 7 hours walking, 351m ascent
The longer walk today extends the morning’s route to incorporate the iconic and much-photographed Cipressi, perhaps Tuscany’s best example of a ring of Cypress trees, all set against golden wheatfields.


Fri - Monticchiello & Montepulciano

Choose between :

Easier Option: 9.2 km, 3 – 4 hours walking, 320m ascent
Today a short complimentary transfer takes our more leisurely walkers to the exquisite village of Montichiello in the morning. Starting from Montichiello, today’s shorter walk approaches Montepulciano through the famous Vino Nobile vineyards before arriving in the hill-top town, another Tuscan gem, just after lunch.

Harder/Longer Option: 15.5 km, 4 – 6 hours walking, 530m ascent
A short complimentary transfer will take you to Pienza. Starting here, the harder walk today passes through the walled village of Montichiello, before passing through the vineyards that produce the famous Vino Nobile di Montepulciano red wine. The walk ends by passing the impressive San Biaggio Cathedral and then climbing up through the historic streets of Montepulciano. It’s a fitting finale to end a week of wonderful walks.


Sat - Departure

Onward independent travel or Collett’s airport transfer.
Our transfer service is likely to depart early, at around 6am, in order to get guests to Pisa Airport in time for mid-morning 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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