Montepulciano to Siena Walking Holidays
Wander amidst Tuscany’s olive orchards and vineyards
Delight in the culinary offerings and famous vintages of the region
Experience the calm ambiance of the quiet village of Montichiello
Take in breathtaking panoramas of classic Tuscan landscapes from the elevated town of Pienza
Discover the secluded Sant’ Antimo Abbey, a masterpiece of Romanesque design
Uncover the mediaeval allure of elevated towns like Montepulciano and Siena
Itinerary
You’ve arrived in the captivating town of Montepulciano, a mediaeval treasure situated in Tuscany’s core. As you enter this delightful locale, the scent of local dishes and the sight of time-honoured structures welcome you. Wander through its stone-paved lanes, explore local boutiques, and immerse yourself in its abundant history. As evening approaches, savour a glass of the renowned Vino Nobile di Montepulciano, setting the mood for the adventures ahead.
Start your day by leaving Montepulciano through one of its ancient gates. Your path leads you across peaceful farmlands, by vineyards and olive orchards, to the quiet hamlet of Montichiello. From there, proceed to Pienza, a UNESCO World Heritage Site celebrated for its Renaissance design and awe-inspiring vistas of the Val d’Orcia.
15 km; 470 m of elevation gain and 520 m of elevation loss
Today’s trek provides awe-inspiring panoramas of quintessential Tuscan landscapes — cypress trees, undulating agricultural lands, and olive orchards. Make a stop in San Quirico d’Orcia, a fortified town featuring a refined 12th-century church and decorative gardens. Continue through Vignoni and reach Bagno Vignoni, a spa village famous for its hot springs.
14 km; 310 m of elevation gain and 490 m of elevation loss
After a calm night and a soothing dip in the morning, follow arid riverbeds through untamed surroundings, with the Ripa d’Orcia castle overlooking the scene. Climb up to the medieval settlement of Castelnuovo dell’Abate.
13 km; 500 m of elevation gain and 470 m of elevation loss
Begin your day with mesmerising views of the valley and its iconic Tuscan landscapes. Pay a visit to Sant’ Antimo, a secluded abbey renowned for its Romanesque Cistercian design. After your abbey visit, traverse the countryside to Montalcino, a hilltop town famous for its Brunello di Montalcino wine.
13 km; 490 m of elevation gain and 470 m of elevation loss
Your walk today guides you through the celebrated Brunello wine territory, alongside vineyards and olive orchards, and into the Crete Senesi’s Tuscan landscapes. Upon entering Buonconvento through its gateway, roam its scenic lanes. For art aficionados, the Museum of Sacred Art of the Val d’Arbia houses works by notable Sienese artists. The town’s name translates to “happy, fortunate place,” and as you explore its peaceful lanes, you’ll see why.
16 km; 280 m of elevation gain and 520 m of elevation loss
Set out from Buonconvento, trekking through the Valle dell’Ombrone towards Lucignano. You’ll enter the town after passing through Monteroni d’Arbia‘s gates. Here, marvel at the imposing Grancia di Cuna, a fortified granary that once stored wheat for the Sienese republic.
10 km; 230 m of elevation gain and 310 m of elevation loss
Leave Lucignano and traverse the Valle dell’Ombrone, offering unforgettable panoramas of the Tuscan landscapes. Your final destination is the historic city of Siena, a UNESCO World Heritage Site celebrated for its mediaeval layout, rich heritage, and lively culture. Here, you have the opportunity to explore the city’s famous museums, savour its renowned dishes, and admire its architectural splendours.
16 km; 230 m of elevation gain and 110 m of elevation loss
As your adventure concludes, take a moment to ponder the indelible experiences and memories you’ve gathered. Whether it’s the breathtaking Tuscan vistas, the deep-rooted history, or the mouthwatering local dishes, this Italian excursion will undoubtedly be a memorable one. Wishing you safe travels!
Want to make some changes?
Pricing
Included in price
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
Luggage transfer
Description
Enter a realm where the clock ticks slower, where the famed ‘la dolce vita’ is not merely a saying but a lifestyle. Prepare for an expedition that leads you into Italy’s soul, bypassing the urban frenzy to bask in the tranquil allure of the Tuscan landscapes. Here, the enchantment of ancient hilltop villages rivals the beauty of sprawling sunflower meadows, olive orchards, and vine-laden hills.
Your journey will guide you through some of Tuscany’s most visually stunning towns, from Montepulciano, a haven for wine aficionados, to Siena, a city that’s an architectural wonder. En route, you’ll encounter the Renaissance elegance of Pienza, the peaceful allure of Castelnuovo dell’Abate, and the mediaeval magnetism of Lucignano, to name a few.
Our walking holidays prioritise your comfort and leisure. The trails are easygoing, the tempo is unhurried, and ample free time is built in for personal exploration. You’ll navigate some of the most picturesque segments of the Via Francigena, an age-old pilgrimage trail focusing on the most scenic towns between Montepulciano and Siena.
At Tuscany Walking Holidays, we manage all the intricacies so you can concentrate on relishing your vacation. We handle accommodation arrangements, furnish you with a comprehensive, written day-to-day plan, and supply GPS guidance through an intuitive app.
So, are you set to exchange your desk chair for a cosy spot in a Tuscan eatery, your daily drive for a leisurely walk amid vineyards, and your morning alarm for the first rays of sunlight filtering through your window? Come discover the Tuscan landscapes with us.
Location
Start planning today!
Things to know
Our tours are designed to cater to a broad range of people, but some days can be quite challenging, with long distances and significant elevation gain. We aim to minimize this as much as possible while ensuring a high-quality experience. To fully enjoy our tours, you should be accustomed to walking for 4-6 hours, overcoming around 600 meters of elevation gain.
However, Alta Via 1 hut-to-hut hikes and Tour du Mont Blanc are more demanding and require a higher fitness level. On these tours, you may need to hike up to 8 hours per day and tackle substantial elevation gain.
Yes, our hiking holidays are appropriate for children who are physically prepared and have a good balance. However, to guarantee the safety and enjoyment of our young participants, we suggest that they should be at least eight years old to join our tours.
Proper footwear is crucial for our walking tours. We recommend wearing sturdy hiking shoes with ankle support for all our hikes. The terrain can be uneven, rocky, and slippery. Wearing sneakers can be dangerous, especially if you are not accustomed to hiking on such surfaces, as they do not offer enough protection and support. Robust shoes also provide the necessary support when your legs get tired during long hikes.
Yes, we highly recommend booking in advance to secure your spot. The earlier you book, the better the chances are of getting your preferred options. If you book close to the start of the season or during the season, we may not be able to guarantee availability in the hotels and apartments. Therefore, it is best to make reservations as soon as possible to avoid any inconvenience.
It is essential to note that accommodations at the destinations of our walking tours are in high demand during the summer season. Therefore, early booking is crucial to secure your preferred type of housing. However, we assure you that we will always try our best to provide you with the most suitable lodging based on your preferences. Rest assured that we will do everything possible to ensure that your stay is comfortable and enjoyable.
Our tours are well-organized, and all the destinations are easily accessible and straightforward to navigate. Therefore, it is unlikely that you will require a guide. Our comprehensive handout will provide you with all the essential information while still allowing you the freedom of a self-guided holiday.
However, if you prefer to have a guide, please let us know, and we will make the necessary arrangements for you.
Most of the accommodations we provide offer vegetarian and vegan options for breakfast. Additionally, you will find no shortage of vegetarian and vegan menus in restaurants during the tour. However, it is worth noting that some mountain huts on Alta Via 1 or Tour du Mont Blanc may not offer vegan meals. In such situations, it is advisable to bring your own food to ensure that your dietary needs are met.
The best time to go on a walking holiday in Italy varies depending on the location you plan to visit. Destinations such as the Amalfi Coast, Cinque Terre, and Sicily are best visited during early spring and fall when the weather is pleasant, and the crowds are fewer.
However, in areas like the Dolomites or around Mont Blanc, hiking is not possible when there is snow high up in the mountains. Therefore, the hiking season in these areas is limited from late June to late September. It is advisable to plan your trip accordingly to get the best out of your walking holiday in Italy.
We can best advise you after receiving a filled-out inquiry form.
While hiking in light rain is manageable, it is important to note that hiking during a storm can be dangerous. It is advisable to schedule hikes early in the day during the summer months to avoid thunderstorms. However, if the weather forecast predicts severe weather, it is best to reschedule your walk for another day or explore different tour options.
Your safety is our top priority, and we will always work with you to find a suitable solution in case of inclement weather.
Most of the destinations for our walking tours in Italy have excellent public transportation. While renting a car can provide flexibility, several locations cannot be comfortably accessed by car. Instead, we suggest relying on public transport to reduce stress and have a more environmentally friendly experience.
We provide all the necessary information for buses, trains, and ferries to ensure that you can reach your destination with ease. By using public transport, we can also reduce our carbon footprint and contribute to a more sustainable travel experience.