Traverse the awe-inspiring terrains of Tuscany and Chianti on foot
Delve into the abundant Renaissance heritage of Siena and Florence
Savour the exceptional local wines of the Chianti region
Trek through undulating hills, taking in the spectacular vistas of the ancient towns beneath
Leverage our meticulously designed itinerary and GPS routes to enhance your exploration
Your Chianti walking tour commences with your arrival in Florence. Absorb the city’s ambience as you explore its magnificent Renaissance structures and charming squares. Enjoy a tranquil stroll along the Arno River‘s banks, taking in the city’s renowned landmarks. Venture towards the Piazza della Signoria, a historic and celebrated square in Florence. As dusk falls, indulge in a gastronomic adventure at one of the local restaurants, where you can sample a variety of delectable Tuscan dishes.
Option A: 8 km, 350 meters of elevation gain and 220 meters of elevation loss (3 hours of walking time)
Option B: 16 km and 570 meters of elevation gain/loss (6 hours of walking time)
Kickstart your day with a hearty breakfast, followed by a short 25-minute bus ride into the tranquil hills of Tuscany. Your walk for the day commences in Settignano, where you can select from two distinct trails. Both paths offer a scenic journey through the breathtaking Tuscan landscape, adorned with aromatic cypress trees, verdant olive groves, majestic Renaissance villas, and panoramic views of Florence. Later, meander through the charming and historic town of Fiesole, dating back to the 7th century, where you can discover intriguing Etruscan ruins, a Roman amphitheatre, and a serene Franciscan monastery.
Option A: 11.5 km and 430 meters of elevation gain/loss (4 hours of walking time)
Option B: 10 km and 350 meters of elevation gain/loss (3.5 hours of walking time)
Start your day with a swift transfer to the delightful town of Greve in Chianti, home to some of the region’s best wines. After settling into your hotel, make your way to Le Cantine di Greve to sample over 50 varieties of local wines. Following this, you’ll have two options for your walk of the day.
The first path originates from Greve’s central square, guiding you through the picturesque Chianti Classico region. Here, you’ll be treated to stunning vistas of expansive vineyards and the “azende agricole” farms, known for their iconic Chianti wine production. The alternative route takes you through the verdant, untamed flora of the neighbouring forest, with olive groves and vineyards marking your path. Along the trail, you’ll encounter deserted farms and magnificent villas, with occasional pauses to appreciate the panoramic view from Montefioralle.
12 km; 400 m of elevation gain and 400 m of elevation loss (4 hours)
Your day’s adventure unfolds with a captivating circular walk commencing in the bewitching village of Panzano. Take some time to wander through the quaint medieval streets of this historic town before setting off on your exploration of the undulating hills.
The quintessential Chianti trail presents a harmonious fusion of natural splendour, oscillating between lush forests and sprawling vineyards, offering ample chances to soak in the mesmerizing landscape of Tuscany. As you traverse the trail, you’ll encounter age-old Roman homesteads, infusing your journey with a dash of historical fascination.
16 km; 600 m of elevation gain and 600 m of elevation loss (5 hours)
Kick off your day with a hearty breakfast, followed by a brief car ride to the awe-inspiring Monte San Michele, the pinnacle of the Chianti hills. From this vantage point, you’ll descend into a picturesque valley, enveloped by towering, centuries-old chestnut trees, and proceed towards the charming medieval village of Volpaia, tucked amidst vineyards and fortresses.
Pause at one of the region’s premier wine boutiques, or “enotecas,” to savour a glass of ruby-red wine before resuming your expedition towards the captivating medieval fortified town of Radda in Chianti.
Embark on today’s adventure with a tour of the quaint old centre of Radda, immersing yourself in the sights and sounds of this historical town. Then, navigate the serpentine alleyways leading you to the magnificent church of Santa Maria Novella. As you stroll through the scenic vineyards, feel free to pause at one of the top-notch local wineries for a sampling of the region’s celebrated wines. The vistas from this walk are guaranteed to leave you spellbound.
Today is yours to relish Siena at your own rhythm and uncover its numerous attractions at your leisure. Begin your day with a delectable breakfast before heading to the stunning city of Siena. This city is a repository of Renaissance history and architectural marvels.
Take in the unique shell-shaped square where the exhilarating Palio horse race takes place twice a year, and explore the awe-inspiring Duomo, a masterpiece of Gothic architecture. Meander through the labyrinthine streets and marvel at the medieval palaces and towers that punctuate the city’s skyline.
Regrettably, all good things must come to an end, and your time with us in Tuscany concludes after breakfast. If your flight schedule allows, you’re invited to discover the city at your leisure.
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* hotels
Transfers as per itinerary
Seize this opportunity to embark on a captivating journey through Tuscany’s undulating hills, vineyards, and historic cities, nourishing your artistic spirit in the land of Michelangelo while exploring the enchanting landscape on foot.
The Chianti trail is the ideal way to experience the region’s most iconic landmarks, such as the medieval cities of Florence and Siena. Additionally, you’ll visit charming hamlets like Panzano and uncover ancient Roman homesteads nestled amongst the hills.
This walking tour features a meticulously designed itinerary highlighting the best of the Chianti region without feeling hurried or overwhelmed. You’ll indulge in a leisurely, well-paced walk each day, with plenty of time to delve into each location and absorb the scenery.
You’ll have the chance to sample some of the world-famous wines of the Chianti region, pausing at local wineries for a glass or two. The walking paths meander through forests and vineyards, offering awe-inspiring views, with your daily outings punctuated by visits to historical landmarks like the church of Santa Maria Novella.
And the cherry on top?
Our team handles every detail, from securing accommodations to providing GPS tracks for each route and a written guidebook to assist you. We offer round-the-clock support and coordinate transfers to ensure a seamless experience.
Unleash your adventurous spirit and immerse yourself in the awe-inspiring beauty of the Chianti region, where paradise awaits to be discovered and cherished!
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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