Tuscany Walking Holiday
- Explore rustic sights & rural landscapes of Italy on this guided walking holiday.
- Stay 7-nights in the spa town of Chianciano Terme.
- Embark on 5 walking days in the Tuscan region, including Montepulciano.
- Experience highlights like Val D'orcia valley, Via Francigena & Cortona.
- Enjoy wine tasting in Montalcino & a guided tour of Siena.
Book Your Trip From €1748pp
Book Your Trip From €1499pp
Your Guided Walking Holiday To Tuscany
Join us on a walking holiday through the breathtaking region of Tuscany, famous for its medieval hill-towns, rich artistic history and beautiful landscapes of rolling hills, cypress trees, olive groves and vineyards. Our hikes will be led by experienced walking guides, where we’ll discover some of the best landmarks of Tuscany and the surrounding area. See the impressive Abbey of Sant'Antimo, visit the ‘Dying City’ of Civita di Bagnoregio and follow the route of Via Francigena taken by the Archbishop of Canterbury in the 10th century on his pilgrimage to Rome. We’ll also have the chance to take a guided tour of Siena, a medieval city best known for the Piazza del Campo, where the iconic Palio horse race is held twice a year. It wouldn’t be a trip to Tuscany without wine tasting, where we’ll savour the world renowned Brunello when we visit Montalcino. Our Tuscany walking holidays offer a perfect blend of culture, history and outdoor recreation.
This holiday is a leisurely walking level. The average daily walking distance on leisurely walks is between 6km – 9.5km, with a maximum daily walking duration of 4 hours.
Activity Level: Active
Travel to Tuscany
Arrive in Italy
Today begins our Italian adventure! Let’s travel to the beautiful region of Tuscany, famous for its outstanding history, culture, wine and cuisine and stunning landscape waiting to be explored on our seven night walking holiday.
Upon our arrival, let’s meet our friendly local representative in the airport and travel together to our hotel based in Chianciano Terme. Surrounded by the beautiful Tuscan countryside, Chianciano Terme enchants visitors both with its historic town centre and its spa facilities, rich in mineral healing waters.
San Quirico D'Orcia to Pienza
Walk the San Quirico D'Orcia & Pienza countryside
After an orientation meeting with our local expert walking guide let’s travel by coach to San Quirico D'Orcia. Let’s wander through the captivating medieval town, enclosed by ancient city walls, and take in the beauty of the Horti Leonini garden, an exquisite creation from 1540. We will then strap up our laces and set out on a leisurely hike with our walking guide through the enchanting Val d’Orcia valley. Let’s discover some of the typical Tuscany countryside among rolling hills of green meadows, vineyards, and rows of cypresses before finishing today’s hike in Pienza. Let’s visit this charming town, the birthplace of Pope Pius II, who transformed it into a splendid papal residence during the Renaissance, before returning to our hotel. A packed lunch is included today for you to enjoy en route.
Difficulty: Leisurely / Distance: 7 km / Duration: approximately 3 hours / Incline: 300 m
Val d’Orcia Valley & Brunello Wine Tasting
Explore the Sant'Antimo Abbey & Val'dOrcia Valley
Let’s start todays walking adventure at the impressive Abbey of Sant'Antimo. After visiting what is probably the most beautiful 12th century Romanesque church in Tuscany, let’s set out on a rewarding hike that treats us to panoramic views of the entire Val d'Orcia and Monte Amiata amongst shady woods and magical vineyards. A packed lunch is included today to eat at your leisure.
Difficulty: Leisurely / Distance: 9.5 km / Duration: approximately 4 hours / Incline: 350 m
Brunello Wine Tasting
Our circular route will bring us back to the Abbey Sant’Antimo from where we will travel to the town of Montalcino. Here let’s enjoy a wine tasting of what is considered the king of Italian wines, the red Brunello wine, and unwind after our full day walking in Tuscany
Civita di Bagnoregio, Lake Bolsena & the Via Francigena
Hike the Calanchi Valley to Civita di Bagnoregio
Let’s let's travel to the neighbouring region of Latium as we travel to the village of Lubriano. From here let’s embark on a captivating hike through the 'Calanchi' Valley, characterized by its intriguing eroded gullies. Our trail leads us to Civita di Bagnoregio, an evocative "Dying City" perched atop a pinnacle, offering breathtaking views of the surrounding vast canyon.
Difficulty: Leisurely / Distance: 4 km / Ascent: 150m / Duration: 2 hours
Explore Lake Bolsena & the Via Francigena
After some time at leisure to explore Civita di Bagnoregio, let’s continue to Lake Bolsena and its namesake the town of Bolsena. Enjoy some free time for lunch before we take a short walk along the historic Via Francigena, once traveled by the Archbishop of Canterbury on his pilgrimage to Rome. We will then finish the day at Montefiascone, situated on the highest of the Volsini hills offering a wonderful view down onto Lake Bolsena.
Difficulty: Leisurely / Distance: 3 km / Ascent: 50m / Duration: 1 hour
Let’s uncover more of Tuscany as we take a rest from hiking today to visit the beautiful town of Siena. Our knowledgeable local guide will lead us on a walking tour through the city's historical marvels, including the iconic shell-shaped Piazza del Campo, where the famous "Palio" horse race is held annually. Let’s also admire the grandeur of the imposing cathedral and immerse ourselves in Siena’s vibrant atmsophere. We will then enjoy some leisure time for lunch and further exploration before returning to the hotel in the afternoon.
Chianciano Terme to Montepulciano
Explore the vineyards of Montepulciano
Let’s hike today through some more beautiful landscapes towards one of Tuscany’s highlights, Montepulciano. First let’s wander through the gentle hills surrounding Chianciano Terme adorned with vineyards producing the wine for which this area is famous. After a slight climb we will reach one of the highlights of Tuscany, Montepulciano.
Let’s admire the 15th century church of San Biagio at the foot of the town before having some free time to explore the town's treasures, including the majestic Piazza Grande, the impressive Palazzo Pubblico, and the Cathedral with its intriguing unfinished façade as well as have lunch. During your stroll through the historic centre, why not treat yourself to a visit to one of the ancient underground wine cellars, where you'll have the chance to taste local specialties and the renowned "Vin Nobile."
Difficulty: Leisurely / Distance: 7.5 km / Ascent: 300m / Duration: 3 hours
Explore the Cortona wine area
Let’s discover more of Tuscany as we explore the Cortona wine area on foot. First let’s begin our day’s walking at the Basilica of Santa Margherita before embarking on a picturesque hike to Villa Bramasole, famed as the setting for the film "Under the Tuscan Sun." We will then continue our exploration along an ancient Roman road to the remarkable Eremo delle Celle, a Franciscan hermitage which exudes tranquility. Finally let’s conclude our day’s adventures in Cortona, where steep cobbled paths lead us through narrow streets that open up to lively squares teeming with daily life. Have some time to enjoy this beautiful Tuscan town and have lunch at your leisure before returning to our hotel.
Difficulty: Leisurely / Distance: 6 km / Ascent: 200m / Duration: 2.5 hours
Today it is time to say ‘ciao’ to the beautiful region of Tuscany as we return home. Let’s head to the airport with wonderful memories of our walking holiday in the Tuscan hills.
Know before you go
Will I be met at the airport?
You will be met on arrival at your destination airport and transferred to your accommodation. You will be accompanied on all included excursions by your TD active guide. Your expert local guide is also available to give you tips and advice on any aspect of your holiday.
Do I need a visa?
Please visit our visa page for information on requirements for each countries entry requirements
What if there is an emergency?
We have local representatives in all of our destinations who are available 24/7 as well as an emergency contact number for our offices in Ireland should you ever need it.