Stroll through the historic streets of Siena, a UNESCO World Heritage Site
Savour the renowned wines of Montepulciano
Discover Pienza, a gem of Renaissance architecture
Enjoy breathtaking views from the hilltop town of Cortona
Explore the vibrant city of Perugia, rich in history and culture
Immerse yourself in the art and architecture of Florence, the cradle of the Renaissance
Welcome to the enchanting city of Siena, a UNESCO World Heritage Site nestled in the heart of Tuscany. As you step into the city, you’ll be captivated by its mediaeval brick buildings and the fan-shaped Piazza del Campo, known worldwide for the famous Palio horse race. Visit the magnificent Siena Cathedral, a masterpiece of Italian Romanesque-Gothic architecture, and marvel at its intricate façade. As the day unfolds, explore the city’s narrow winding streets, filled with traditional shops and cafes. End your day with a delightful Tuscan meal, savouring the flavours of local dishes like Pici pasta and Panforte.
Spend the morning discovering more of Siena’s hidden gems. In the afternoon, embark on a scenic train journey to Montepulciano, a mediaeval and Renaissance hill town famous for its Vino Nobile wine. Upon arrival, a transfer will whisk you away to your hotel. Spend the evening at leisure, perhaps sampling some of the local wine and soaking in the stunning views of the surrounding vineyards.
Today, a short bus ride takes you to Pienza, a charming Renaissance town nestled in the heart of the picturesque Val d’Orcia. Spend the day exploring its quaint streets, visiting the beautiful Pienza Cathedral, and sampling the town’s famous pecorino cheese. In the afternoon, set off on foot across the stunning landscape back to Montepulciano, enjoying the serene beauty of the Tuscan countryside.
14 km; 600 m of elevation gain and 500 m of elevation loss
Start your day with a leisurely walk from Montepulciano to Valiano, a quaint village surrounded by lush vineyards. From Valiano, a transfer will take you to the hilltop town of Cortona, known for its stunning views over the Chiana Valley and Lake Trasimeno. Spend the rest of the day exploring Cortona’s charming streets and vibrant squares, and don’t miss the chance to visit the Museo Diocesano, home to works by Fra Angelico and Luca Signorelli.
14.5 km; 200 m of elevation gain and 450 m of elevation loss
Today’s journey takes you on a walk from Cortona to Tuoro, a town steeped in history and known for the Battle of Lake Trasimeno. As you traverse the scenic paths, take in the breathtaking views of the surrounding countryside. Spend the night in Tuoro, resting up for the next day’s adventure.
14 km; 300 m of elevation gain and 550 m of elevation loss
Board a train to Perugia, the capital of Umbria, a city renowned for its defensive walls dating back to the Etruscan period. Spend the day exploring the city’s rich history, from the mediaeval centre to the beautiful Palazzo dei Priori. Don’t miss the chance to sample some local Umbrian cuisine, such as the delicious torta al testo.
Start your day with a bus ride to Tavernelle, a town with a rich history. From there, walk to Panicale, a charming mediaeval village known for its beautiful frescoes and panoramic views of Lake Trasimeno. After a day of exploration, take a bus back to Perugia for a well-deserved rest.
16 km; 240 m of elevation gain/loss
Bid farewell to Perugia as you board a train to Florence, the cradle of the Renaissance. Spend the day immersing yourself in the city’s world-renowned art and architecture. Visit the iconic Duomo, stroll across the Ponte Vecchio, and explore the masterpieces housed in the Uffizi Gallery. As the sun sets, enjoy a traditional Florentine steak paired with a glass of Chianti.
Embark on a walk to Fiesole, a town known for its archaeological sites and panoramic views of Florence. Spend the day exploring the Roman amphitheatre, the Etruscan walls, and the Franciscan Monastery. Return to Florence in the evening, perhaps enjoying a gelato as you stroll along the Arno River.
17.5 km; 400 m of elevation gain/loss
Your Italian adventure comes to an end in the beautiful city of Florence. Spend your last morning reminiscing about your journey, perhaps visiting the Mercato Centrale for some last-minute souvenir shopping. As you prepare for your departure, take one last look at the city’s stunning skyline, a beautiful reminder of your unforgettable journey through Italy. 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
9x accommodation with breakfast in 3/4* hotels
Transfers as per itinerary
Can we paint a picture for you?
You’re meandering through a patchwork of vineyards, their ripe grapes glistening under the Tuscan sun. The gentle undulation of the emerald hills stretches out before you, a living canvas of Italy’s heartland. On the horizon, the stone towers of a mediaeval town rise, whispering tales of yesteryears and inviting you to uncover their secrets.
These are the Walking Holidays in Tuscany and Umbria, in essence.
Your journey will take you through the charming towns of Siena, Montepulciano, Pienza, Cortona, Perugia, and Florence. Each town, a treasure trove of history, art, and culture, offers its unique charm.
From Siena’s shell-shaped Piazza del Campo to the Renaissance beauty of Pienza. From the hilltop town of Cortona to the vibrant city of Perugia and finally to Florence, the cradle of the Renaissance.
The hikes are leisurely, allowing ample time to soak in the scenery, delve into the local culture, and truly experience the Italian way of life. You’ll walk through some of the most picturesque cities in Tuscany and Umbria, with plenty of time to discover hidden gems, sample local delicacies, and simply sit back and enjoy the view.
We oversee and book all the accommodations, ensuring you have a comfortable place to rest after a day of exploration. We provide a detailed handout with a day-by-day itinerary, complete with GPS navigation via a user-friendly app.
You’ll also receive local recommendations to help you discover the best each town has to offer. And if any logistical issues arise, we’re here to solve them, so you can focus on enjoying your holiday.
Are you ready to swap your office chair for a seat in a quaint Italian café, your daily commute for a walk through sun-drenched vineyards, and your alarm clock for the tolling of a mediaeval bell tower? After all, why just visit Italy when you can walk it?
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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