Women only Walking in Tuscany tour
21 – 26 September 2026
TOUR DESCRIPTION
Walking in Tuscany is a journey designed as a six-day experience, giving you the freedom to shape your wider travels in Italy or Europe before, or, after the tour.
This gentle walking journey through the heart of Tuscany is an invitation to slow down, breathe deeply, and immerse yourself in one of Italy’s most beautiful landscapes. Set high in the Val d’Orcia countryside, Podere Spedalone is one of those places that gently resets your pace. Surrounded by rolling hills, cypress lined roads and open skies, it feels timeless, grounded and quietly restorative.
For this walking tour, I’ve chosen to keep the stay here intentionally small allowing the group to remain intimate and experience unhurried. The group is limited to 6 ladies only. Mornings begin with light filtering through stone windows, the scent of coffee drifting through the farmhouse, and the simple pleasure of knowing you don’t need to be anywhere in a rush.
Evenings are equally special – honest Tuscan food, long tables, good conversation and the kind of stillness that’s becoming harder to find. With fewer guests, there’s space to settle in, to be known by name, and to feel part of the rhythm of the place rather than a visitor passing through.
This is not about having more.
It’s about having enough – space, beauty, connection and ease.
WOMEN ONLY
30% deposit to book your place
ZAR 43 500 single
ZAR 35 500 pp sharing- INCLUDED IN THE TOUR:
- Airport transfer from Rome or Florence
- Accommodation: Podere Spedalone – rooms are limited
- Full board
- Cooking class
- Wine tasting
- Professional English-speaking tour guides
- Not Included: International flights, travel insurance (I can assist), visas, personal drinks, optional activities, gratuities and tips.
Because of the limited number of rooms, early enquiries are recommended.
Your Local Guide In Tuscany
We will be led by a wonderful local Italian woman, Federica, who will be with the group throughout as our driver and on-the-ground host. She knows this region intimately – from the quieter back roads to the villages and landscapes that define daily life here. We will also be joined by local walking guides on selected walks, adding depth and insight to the landscapes you explore.
This shorter, well-paced tour allows space, whether that means arriving early, lingering longer in Italy, or continuing on to spend time with family elsewhere in Europe.
Our Tour
ITINERARY
DAY 1
A Tuscan Welcome
Ciao bellissime!
Your morning transfer from Rome or Florence takes you to the enchanting Renaissance town of Pienza, set high above the rolling hills of the Val d’Orcia – a UNESCO World Heritage landscape famed for its symmetry, light and timeless beauty.
San Quirico d’Orcia to Bagno Vignoni
After lunch at Podere Spedalone, meet your host and learn about the next few days. Your journey begins in the village of San Quirico d’Orcia, with a gentle walk along the ancient Via Francigena – a historic pilgrimage route that has carried travellers, seekers and storytellers through Tuscany for centuries. The path unfolds across open countryside, with cypress-lined horizons and the unmistakable calm of the Val d’Orcia, arriving in the unique village of Bagno Vignoni, famous for its steaming thermal waters that fill the central piazza. Towards evening, settle in for a relaxed aperitif followed by dinner, enjoying your first taste of Tuscan hospitality in a setting that feels both timeless and quietly magical.
Transfer to Podere Spedalone: A morning transfer will be coordinated from Rome or Florence, ensuring a smooth and relaxed start to your time together.
Walk: Easy | 5 km
Accommodation: Podere Spedalone – 14thcentury farmhouse
Meals: Lunch, dinner
DAY 2
Pienza & The Iconic Vitaleta Chapel
After breakfast, a short transfer takes you into Pienza, where your guide will share the story of this perfectly proportioned Renaissance town, created as an ideal city during the 15th century.
From here, you set out on a beautiful walk through classic Tuscan scenery towards the much photographed Vitaleta Chapel. Poised gracefully on a gentle hill, the chapel’s simple elegance – framed by cypress trees and soft, undulating fields – captures the very soul of Tuscany.
A relaxed picnic lunch is enjoyed along the way before continuing the walk. Transport will return you to the Agriturismo later in the afternoon.
Walk: Moderate | 10.5 km
Meals: Breakfast, picnic lunch, dinner
DAY 3
Montalcino, Sant'Antimo & Brunello
Today’s walk unfolds in the celebrated Montalcino region, leading you to the Abbey of Sant’Antimo. This 12thcentury Romanesque monastery sits serenely among vineyards and olive groves and is considered one of Tuscany’s most evocative spiritual sites.
Along the way, you’ll stop for a light lunch and Brunello wine tasting at a local cellar, gaining insight into the craftsmanship behind one of Italy’s most prestigious wines – renowned for its deep ruby hue, bold aromas and remarkable aging potential.
You’ll appreciate every step of today’s walk – especially after the wine!
Walk: Moderate | 9 km
Meals: Breakfast, lunch, dinner
DAY 4
Montefollonico & Montepulciano
This morning begins in Montefollonico, a quietly enchanting hilltop village where life still moves at a gentler pace. Wander its narrow lanes and step into the workshop of a local artisan ceramicist, offering a glimpse into a craft shaped by tradition and time. A visit to a beautifully kept panoramic garden follows, a peaceful spot to pause and take in sweeping views of the Val d’Orcia.
From here, set off on foot towards Montepulciano. The walk is one of the loveliest of the week, unfolding through the rolling vineyards of Vino Nobile. In September, the vines are heavy with ripening grapes, and Montepulciano rises steadily in the distance.
The final ascent into Montepulciano is undeniably steep. It’s known as the queen of hilltop towns. For this reason, you will take a small red tourist bus from the Temple of San Biagio (the end point of your walk) up to the Fortezza.
After lunch, time to explore its Renaissance palazzi, winding streets and vibrant piazzas.
Walk: Easy | 6 km
Meals: Breakfast, lunch, dinner
DAY 5
Podere Spedalone - Cooking, Rest & Renewal
Today is devoted to the simple pleasures of Tuscan living. Begin with a hands-on cooking class at Podere Spedalone, learning traditional recipes rooted in local produce and family tradition.
The remainder of the day is yours to enjoy at leisure. Relax by the outdoor pool, treat yourself to a spa experience, wander the grounds, or simply sit with a glass of wine and take in the sweeping Val d’Orcia views.
Meals: Breakfast, lunch, dinner
DAY 6
Farewell Tuscany - Transfer to Rome or Florence
After breakfast, your transfer will take you back to Rome or Florence.
As your journey through Tuscany’s rolling hills, ancient villages and vineyarddotted landscapes comes to an end, we hope the beauty, warmth and flavours of this region stay with you long after you return home.
Thank you for being part of this walking adventure. May the spirit of Tuscany continue to inspire your steps.
Buon viaggio e arrivederci.
Meals: Breakfast
Our walking/hiking trip to Florence and Tuscany, with The Adventurous Ewe women’s tour group, was wonderful! Well organised, all bases such as travel and transfers, meals, accomodation and hiking destination , superb and remarkably excellent. Highly recommended! Thank you Mandy for ensuring we had a most memorable Tuscany hiking experience!
This was my first group tour other than family trips and I had such a good time. We enjoyed delicious food and wine, and the company of fellow travellers was great fun. The views from the top of the Apennines are spectacular, and there was always gelato to revive the company. I am sold on small group tours and am so appreciative of Mandy who was attentive and organized and has become a friend. I’m trying to decide between Portugal and Turkey for next year and definitely Morocco in 2026.
This was a suberb tour, walking the hills of Tuscany.It was beautifully crafted taking us through Chestnut forests, old towns like Lucca and Barga, and relaxing for two days in inspiring Florence. The accommodation was wonderful and the food and wine plentiful and delicious.I would highly recommend The Adventurous Ewe to any one wanting a fun,relaxed holiday with a small group of like minded ladies.