The Val d’Orcia region, famous for its rolling hills, winding cypress-lined roads, charming farmhouses, and hilltop villages, is the backdrop for this exciting journey. You'll hike scenic, accessible trails that are perfect for travellers new to walking adventures, making it an ideal choice for those wanting to dip their toes into international hiking.
Each day, you’ll explore quaint medieval towns, enjoy authentic Tuscan cuisine, and immerse yourself in local culture. From visiting the iconic village of Montalcino to soaking in the rejuvenating thermal springs of Bagno Vignoni, this trip has it all - stunning landscapes, cultural insights, and plenty of moments to bond with your fellow adventurous women.
Whether you’re ticking Tuscany off your bucket list or simply looking for a friendly, supportive environment to try something new, this tour is designed to inspire confidence and create lasting friendships.
● Explore Pienza - Discover this charming hilltop town with stunning views and historic sites.
● Hike Through Montepulciano & Monticchiello - Visit these picturesque Tuscan villages and enjoy a local winery lunch.
● San Quirico d'Orcia - Walk through scenic countryside to a lesser-known, authentic Tuscan village for a relaxing picnic.
● Relax in Bagno Vignoni’s Thermal Springs - Unwind in ancient thermal waters known for their therapeutic benefits.
● Visit Sant'Antimo Abbey - Hike through the Brunello wine region and explore this beautiful Romanesque abbey.
● Brunello Wine Tasting - Enjoy wine tasting at a local vineyard, sampling the famous Brunello di Montalcino.
● Walk with Like-Minded Women - Share this adventure with a group of welcoming, supportive women, making new friendships and memories along the way.
● Engage with Locals - With your expert local guide, you will gain insider knowledge of the region and have the opportunity to interact with the people who call this beautiful area home.
We’ll kick off the adventure by meeting at Florence Airport for a late morning transfer to the charming hilltop town of Pienza. With its stunning views and rich history, it’s the perfect place to start our journey. Once we’ve settled into our cosy hotel, we’ll enjoy a leisurely lunch filled with local specialties before stretching our legs on a relaxed hike to Petroio and Sant’Anna in Camprena. Afterwards, feel free to explore the village at your own pace. As the day winds down, we’ll gather for a tour overview accompanied by an aperitivo, followed by our first group dinner – the perfect time to get to know one another and share our excitement for the days ahead.
Meals: Lunch, Dinner
Accommodation: Hotel in Pienza
Today, we’ll hike through the breathtaking Tuscan countryside, stopping by the postcard-perfect villages of Montepulciano and Monticchiello. Along the way, we’ll enjoy lunch at a local winery – because what’s a trip to Tuscany without a bit of wine tasting? After returning to Pienza, you’ll have time to explore the historic Papal Palace and cathedral. We will meet for dinner and the evening will be spent together, reminiscing about the day’s adventures.
Meals: Breakfast, Lunch, Dinner
We’ll start our day hiking through the open countryside to the medieval village of San Quirico d'Orcia, where you can shop for local treats at the deli and enjoy a laid-back picnic in a beautiful rose garden - why not top off lunch with a well-deserved gelato? Later, it’s all about relaxing by the pool and watching the Tuscan sunset. Tonight, we’ll get together for a presentation on the Via Francigena, giving us a deeper connection to the history of the paths we’ve been walking, followed by dinner at the hotel restaurant.
Meals: Breakfast, Dinner
Accommodation: Hotel Palazzuolo
Today’s hike takes us to the quaint village of Bagno Vignoni, where the famous thermal springs have been soothing visitors for centuries. After stopping for lunch in the lovely hamlet of Vignoni Alto, we’ll wind our way through vineyards and oak forests until we reach Bagno Vignoni. Spend the afternoon soaking in the thermal pools or treating yourself to a massage - it’s all about relaxation today! We’ll head back to San Quirico in the evening, where you can enjoy dinner on your own and chat about the day with your new friends.
Meals: Breakfast
Accommodation: Hotel Palazzuolo
On our last full day, we’ll embark on one of the most rewarding hikes of the trip, walking through lush woodlands and iconic Brunello vineyards to the historic Sant’Antimo Abbey. After a picnic lunch in the peaceful surroundings, we’ll visit a Brunello winery to learn about the art of winemaking and indulge in a tasting. In the evening, we’ll wrap up our adventure with a celebratory dinner in Montalcino - the perfect chance to toast new friendships and reflect on the incredible journey we’ve shared.
Meals: Breakfast, Dinner
Accommodation: Hotel Palazzuolo
It’s time to say goodbye - but not before one last breakfast together. Afterward, we’ll transfer back to Florence Airport for your departure. Book your flight for after 2 pm to ensure a smooth, relaxed end to this adventure. Take with you new friendships, unforgettable experiences, and the empowerment of having explored this incredible region alongside other adventurous women.
Meals: Breakfast
Adventurous Women Tour Leader
Local Guide
5 nights at 3-star hotels w/breakfasts (one with pool)
4 dinners
2 lunches
2 wine tastings
All transportation and entrances during the trip
Bagno Vignoni thermal pools entrance
One city tour with guide (Montalcino)
Use of walking poles
2 Lunches
4 Dinners
5 Breakfasts
Flights to/from Florence
Travel Insurance (recommended)
- - Detailed Trip Notes will be provided well in advance of your departure, to help you plan & prepare.
Notice of cancellation must be in writing, with an email as an acceptable form of communication, directly to Adventurous Women with the following conditions:
No refund is available after departure of a tour has commenced.
We highly recommend taking trip cancellation cover through your travel insurer to cover you for unforeseen circumstances that may lead you to have to cancel your participation in the tour.
