Stroll through the vineyards and olive groves of Tuscany
Explore the mediaeval charm of hilltop towns like Montepulciano and Siena
Savour the flavours of local cuisine and world-renowned wines
Experience the tranquillity of the peaceful village of Montichiello
Marvel at the stunning views of the iconic Tuscan scenery from the hilltop town of Pienza
Visit the isolated Sant’ Antimo Abbey, a gem of Romanesque architecture
Welcome to the enchanting town of Montepulciano, a mediaeval jewel nestled in the heart of Tuscany. As you step into this charming town, you’ll be greeted by the aroma of local cuisine and the sight of ancient buildings. Spend your day exploring the cobblestone streets, visiting the local shops, and soaking in the rich history. As the sun sets, enjoy a glass of the famous Vino Nobile di Montepulciano as you prepare for the adventures that await.
Begin your day by exiting Montepulciano through one of its historic gates. Your journey takes you through the serene countryside, past vineyards, and olive groves, to the tranquil village of Montichiello. Continue your journey to Pienza, a UNESCO World Heritage Site known for its Renaissance architecture and stunning views of the Val d’Orcia.
15 km; 470 m of elevation gain and 520 m of elevation loss
Today’s walk offers breathtaking views of the typical Tuscan scenery of cypress trees, rolling farmland, and olive groves. Stop in San Quirico d’Orcia, a walled town with an elegant 12th-century church and ornate gardens. Pass through Vignoni and arrive in Bagno Vignoni, a spa town known for its thermal baths.
14 km; 310 m of elevation gain and 490 m of elevation loss
Today, you will leave Bagno Vignoni and follow dry riverbeds through a wild environment, with the castle on the hill, Ripa d’Orcia, dominating the view. Ascend into the mediaeval village of Castelnuovo dell’Abate.
13 km; 500 m of elevation gain and 470 m of elevation loss
Start your day with stunning views of the valley and its iconic Tuscan scenery. Visit Sant’ Antimo, an isolated abbey known for its Romanesque Cistercian architecture. After exploring the abbey, continue across the land to Montalcino, a hill town known for its Brunello di Montalcino wine.
13 km; 490 m of elevation gain and 470 m of elevation loss
Today’s walk takes you through the famous Brunello wine region, past vineyards, and olive groves, and into the Tuscan landscape of the Crete Senesi. As you enter Buonconvento through its gate, explore its picturesque streets. Art lovers can admire works of famous Sienese painters in the Museum of Sacred Art of the Val d’Arbia. The town’s name means “happy, fortunate place,” and as you wander its tranquil streets, you’ll understand why.
16 km; 280 m of elevation gain and 520 m of elevation loss
Begin your journey from Buonconvento, walking through the Valle dell’Ombrone towards Lucignano. You’ll make your way to the town, passing through the gates of Monteroni d’Arbia. There you can admire the impressive Grancia di Cuna, a fortified farm that once held wheat reserves for the republic of Siena.
10 km; 230 m of elevation gain and 310 m of elevation loss
Depart from Lucignano and journey through the Valle dell’Ombrone, offering unforgettable views of the Tuscan countryside. Your destination is the historic city of Siena, a UNESCO World Heritage Site known for its mediaeval cityscape, rich history, and vibrant culture. Here, you can explore the city’s renowned museums, indulge in its famous cuisine, and witness the grandeur of its architecture.
16 km; 230 m of elevation gain and 110 m of elevation loss
As your journey comes to an end, take some time to reflect on the unforgettable experiences and memories you’ve made. Whether it’s the stunning Tuscan landscapes, the rich history, or the delicious local cuisine, this trip to Italy will surely be one to remember. Safe travels!
Not enough? Why not spend a few more days here! Extend your holidays with a pre- or post-holiday extension. Accommodation, sightseeing, and activities can be arranged. Add as many extra days to your holiday as you wish.
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Tour design and organisation
24/7 service and support during your holidays
GPS navigation with an easy-to-use app
7x accommodation with breakfast in 3/4* hotels
Step into a world where time slows down, where the sweet life, or ‘la dolce vita,’ isn’t just a phrase but a way of being. It’s time for a journey that takes you to the heart of Italy, not through the hustle and bustle of its cities but through the serene beauty of the Tuscan countryside. Here, the charm of mediaeval hilltop towns competes with the allure of sunflower fields, olive groves, and rolling vineyards.
Your adventure will take you through some of the most picturesque towns in Tuscany, from the wine-lovers paradise of Montepulciano to the architectural marvel of Siena. Along the way, you’ll discover the Renaissance splendour of Pienza, the tranquil beauty of Castelnuovo dell’Abate, and the mediaeval charm of Lucignano, among others.
Each town is a gem waiting to be explored, set against the backdrop of Tuscany’s iconic rolling hills and cypress-lined roads.
Our walking holidays are designed with leisure in mind. The hikes are gentle, the pace is relaxed, and there’s plenty of time to explore on your own. You’ll traverse some of the most scenic parts of the Via Francigena, an ancient pilgrimage route, and focus on the most picturesque cities between Montepulciano and Siena.
At Tuscany Walking Holidays, we take care of all the details so you can focus on enjoying your holiday. We oversee the accommodation availability and secure all the bookings, provide a detailed written handout with a day-by-day itinerary, and offer GPS navigation with a user-friendly app.
So, are you ready to swap your office chair for a seat at a Tuscan trattoria, your daily commute for a stroll through a vineyard, and your alarm clock for the morning sun streaming through your window? Come and lose yourself in the Tuscan countryside with us.
Our walking holidays in Tuscany are primarily focused on leisurely exploration, offering a delightful experience without significant elevation gain. However, it’s important to note that certain stages of the Via Francigena can be quite long. In addition, we also offer other holiday options that include more demanding hikes. Regardless of the holiday you choose, we aim to provide a high-quality experience catering to different fitness levels. So, whether you prefer leisurely strolls through the picturesque Tuscan countryside or more demanding hikes to push your limits, we have options to suit your preferences and ensure a fulfilling journey.
Absolutely! Our hiking holidays are designed to be inclusive and can be enjoyed by people of various age groups, including children. Most of our tours do not include technically demanding terrain. We believe in the importance of providing opportunities for children to embrace the outdoors and experience the joys of hiking. While a minimum age of eight is recommended to ensure safety and engagement, our tours are generally suitable for individuals who possess basic physical capabilities and can comfortably walk for a few hours daily.
For our walking tours, we highly recommend wearing sturdier hiking shoes that provide ample support, particularly during long hiking days and on uneven terrain. Hiking shoes are designed specifically for outdoor activities, offering features such as sturdy soles, enhanced traction, and ankle support. They are well-suited to handle various terrains, including gravel paths, rocky trails, and uneven surfaces commonly encountered during our walking tours. Opting for appropriate footwear ensures comfort and stability and minimises the risk of foot fatigue or potential injuries.
We highly recommend making an advance booking to ensure accommodation availability. Securing your reservation early increases the likelihood of obtaining your preferred options. If you wait until the start of the season or during the season, availability in hotels and apartments may be limited, and we may not be able to guarantee your desired arrangements.
It’s important to be aware that accommodations at the destinations are in high demand, especially during the summer season. To secure your preferred type of housing, we strongly recommend booking early. By doing so, you increase the likelihood of obtaining the accommodation that best suits your preferences. While the availability of specific lodging options may vary, we assure you that we will make every effort to provide you with the most suitable accommodations based on your preferences. Our team is dedicated to ensuring your stay is comfortable and enjoyable, and we strive to meet your specific requirements to the best of our ability.
Our tours are meticulously planned and designed to be easily navigated by independent travelers. The destinations are well-marked and accessible, allowing you to explore at your own pace. As such, it is unlikely that you will require a guide during your tour.
To ensure you have all the necessary information and guidance, we provide a comprehensive handout that covers essential details about the routes, points of interest, and practical tips. This enables you to enjoy the freedom and flexibility of a self-guided holiday, where you can fully immerse yourself in the experience and discover the beauty of each destination at your leisure.
However, if you prefer to have a guide accompany you during the tours, we are more than happy to accommodate your request. Simply let us know in advance, and we will make the necessary arrangements to provide you with a knowledgeable guide who can enhance your journey with insightful commentary and assistance.
The best time to go on a walking holiday in Tuscany is during the early spring and fall seasons. During these periods, the weather is pleasant, and the crowds are fewer, allowing for a more tranquil and enjoyable experience.
In the early spring, typically from March to May, you can witness the region come alive with vibrant blossoms and lush greenery. The temperatures are mild, making it perfect for exploring the picturesque landscapes of Tuscany on foot. Additionally, the tourist crowds are relatively smaller during this time, providing you with a more intimate and serene setting to immerse yourself in the beauty of the surroundings.
Similarly, the fall season, from September to November, offers a delightful time to visit. The weather remains pleasant, with comfortable temperatures ideal for walking and exploring. The autumn colours add a captivating charm to the landscapes, creating a picturesque backdrop for your walking tour. With fewer visitors compared to the peak summer months, you can fully appreciate the tranquillity and authenticity of the region.
It’s worth noting that the summer months in Tuscany, particularly July, and August, can be quite hot and crowded. While the region maintains its allure during this time, the higher temperatures and increased tourist influx may impact your overall experience. However, if you plan accordingly and take precautions against the heat and the crowds, summer can still offer enjoyable walking opportunities in Tuscany.
In cases of light rain or mild weather disturbances, hiking can often still be safely managed as long as it does not pose any significant risks. The stunning landscapes of Tuscany can take on a unique charm under a drizzle, offering a different perspective and an enchanting experience.
However, in situations where the weather becomes more severe, such as heavy rainstorms or thunderstorms, our team will assess the situation and make appropriate adjustments to ensure your safety. This may involve modifying the planned routes, seeking shelter, or postponing the activity until the weather improves.
Those who like a good adventure and limitless flexibility should go on a self-guided tour. We prepare the itinerary and book your accommodations while you enjoy the journey without our guide, being fully in charge of all the daily decisions. While you’ll have the full support of our team in case of any emergencies or concerns, a certain level of self-reliance is required.
Experience the great outdoors on a private guided tour tailored just for you. The tour is for those who want a hastle-free adventure and enjoy the flexibility of a small private group and not stress about the details of everyday planning. The guide will be fully at your disposal to make this experience as personalized as possible, maximizing the enjoyment during and after the tour.
For solo hikers or hikers who wish to meet other like-minded souls, don’t want to stress about tour-planning and other annoying details. We’re going to find you a group of like-minded outdoor enthusiasts and take care of all the other details. The tour will be led by our guide, who’ll make sure everything runs smoothly, ensuring maximum hiking enjoyment.
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