Trails of Tuscany & Umbria
Trails of Tuscany & Umbria
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Let yourself be surprised by an unforgettable journey that begins in Tuscany and ends in Umbria, among golden landscapes, vineyards and the spiritual heart of Italy. Over ten days of gentle, scenic walks, you will explore rural trails, medieval villages and vibrant Renaissance cities. A tour of the best of Italy, perfectly combining culture and immersion in iconic landscapes through walking.
- Begin your adventure in Siena, a historic city of red bricks and lively squares, with time to admire its art and cathedral.
- Venture into the Val d'Orcia, walking among golden hills and olive groves until you reach charming villages such as Pienza, Montepulciano and Cortona, all surrounded by vineyards and cypress fields.
- Arrive in picturesque Umbria, where gentle trails will take you through olive groves, sunflowers and the intense green of its nature.
- Enjoy Italian cuisine: Tuscan wines, pecorino cheese, local cold cuts, artisan bread and Umbrian truffles.
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Itinerary
Day 1 - Arrival in Siena
The first day begins in Siena, a medieval gem nestled among rolling hills, where every street seems to tell a story. Arriving in this city is like stepping back in time: brick towers, Gothic façades and vibrant squares that preserve the soul of the past.
Explore the heart of the city, the famous Piazza del Campo, the setting for the historic Palio and a meeting point for locals and travellers alike. Take your time to lose yourself in its narrow streets, enjoy an espresso in the sun or toast with a glass of local wine while you soak up the essence of la dolce vita.
Explore the heart of the city, the famous Piazza del Campo, the setting for the historic Palio and a meeting point for locals and travellers alike. Take your time to lose yourself in its narrow streets, enjoy an espresso in the sun or toast with a glass of local wine while you soak up the essence of la dolce vita.
Overnight in Siena
La Chicca B&B
This family-run accommodation offers spacious rooms with fans and central heating. It is located in an old villa in San Prospero, just outside the historic walls of Siena.
It also has a beautiful garden where you can relax.
*In case this accommodation is not available, you will stay in a similar category hotel.
Day 2 - Siena to Montepulciano
You will have the morning free to continue exploring the Gothic charms of Siena, a city declared a World Heritage Site by UNESCO. Stroll through its medieval streets, stop at a shop selling local products or join in and let yourself be surprised by the local cuisine, tasting homemade pasta dishes, olive oil, cheeses and local wines.
After lunch, you will embark on a picturesque train journey through the Tuscan countryside, full of rolling hills covered with vineyards and cypress trees. The journey takes about an hour and offers views that give you a taste of the beauty of the days to come. You can check timetables and further information about trains on the Trenitalia website.
Upon arrival at the station, you will have a transfer included to your accommodation in Montepulciano, a charming Renaissance village perched on a hill. As evening falls, you can enjoy a glass of the famous Vino Nobile di Montepulciano, while the sun paints the stone facades gold.
Don't forget to bring your luggage with you on this day.
After lunch, you will embark on a picturesque train journey through the Tuscan countryside, full of rolling hills covered with vineyards and cypress trees. The journey takes about an hour and offers views that give you a taste of the beauty of the days to come. You can check timetables and further information about trains on the Trenitalia website.
Upon arrival at the station, you will have a transfer included to your accommodation in Montepulciano, a charming Renaissance village perched on a hill. As evening falls, you can enjoy a glass of the famous Vino Nobile di Montepulciano, while the sun paints the stone facades gold.
Don't forget to bring your luggage with you on this day.
Overnight in Montepulciano
Hotel Albergo Il Marzocco
Located in a tastefully decorated 19th-century country house, this accommodation offers a warm and welcoming atmosphere.
This accommodation features free Wi-Fi, air conditioning and a private bathroom.
*In case this accommodation is not available, you will stay at a similar category one.
Day 3 - Enjoy your day exploring the surroundings of Montepulciano 8,7 miles | 14 km
This morning, you will begin with a transfer to Pienza, a Renaissance town declared a UNESCO World Heritage Site, famous for its architectural harmony and for producing one of the most exquisite pecorino cheeses in all of Tuscany.
Designed in the 15th century as the “ideal city” at the behest of Pope Pius II, Pienza captivates visitors with its balance, history and open views of the valley. Part of the old town and its surroundings served as the setting for the film The English Patient, especially the nearby Monastery of Sant'Anna in Camprena. A walk along the southern wall offers one of the most impressive panoramic views of the Val d'Orcia.
From here, you will begin your walk back to Montepulciano, with the option of stopping at Monticchiello, a fortified village with cobbled streets and perfect spots for a picnic with a view.
If you prefer a quieter day, you can stay and explore Montepulciano at your own pace. The Church of Sant'Agostino, the Palazzo Comunale with its panoramic tower and the Piazza Grande invite you to immerse yourself in their historic atmosphere. For a delicious break, the historic Caffè Poliziano is ideal for a lunch with local style and flavour.
Designed in the 15th century as the “ideal city” at the behest of Pope Pius II, Pienza captivates visitors with its balance, history and open views of the valley. Part of the old town and its surroundings served as the setting for the film The English Patient, especially the nearby Monastery of Sant'Anna in Camprena. A walk along the southern wall offers one of the most impressive panoramic views of the Val d'Orcia.
From here, you will begin your walk back to Montepulciano, with the option of stopping at Monticchiello, a fortified village with cobbled streets and perfect spots for a picnic with a view.
If you prefer a quieter day, you can stay and explore Montepulciano at your own pace. The Church of Sant'Agostino, the Palazzo Comunale with its panoramic tower and the Piazza Grande invite you to immerse yourself in their historic atmosphere. For a delicious break, the historic Caffè Poliziano is ideal for a lunch with local style and flavour.
Overnight in Montepulciano
Hotel Albergo Il Marzocco
Located in a tastefully decorated 19th-century country house, this accommodation offers a warm and welcoming atmosphere.
This accommodation features free Wi-Fi, air conditioning and a private bathroom.
*In case this accommodation is not available, you will stay at a similar category one.
Day 4 - Montepulciano to Cortona 5,8 miles | 9,4 km
Today you will leave Montepulciano behind and venture into the iconic Tuscan countryside, walking among rolling hills, golden fields and small villages perched above the landscape. This peaceful route will take you to Acquaviva, passing through a typically Tuscan setting that looks like something out of a postcard.
From Acquaviva, you will have a transfer included to the charming town of Cortona, where you will arrive in the afternoon. Located at an altitude of 600 metres, this medieval town welcomes you with its serene atmosphere and steep stone streets. It is the perfect place to take a break, find a sunny terrace and enjoy watching the slow pace of local life.
Once in Cortona, be sure to visit the Etruscan Academy Museum, founded in 1727, which preserves a valuable artistic and archaeological legacy. And to end the day, there is nothing better than a walk to Piazza Garibaldi, where the views open up to the valley in a breathtaking panorama.
If you are looking for a longer walk, there is the option of continuing on foot from Acquaviva to Valiano, extending the walk until the final transfer to Cortona.
From Acquaviva, you will have a transfer included to the charming town of Cortona, where you will arrive in the afternoon. Located at an altitude of 600 metres, this medieval town welcomes you with its serene atmosphere and steep stone streets. It is the perfect place to take a break, find a sunny terrace and enjoy watching the slow pace of local life.
Once in Cortona, be sure to visit the Etruscan Academy Museum, founded in 1727, which preserves a valuable artistic and archaeological legacy. And to end the day, there is nothing better than a walk to Piazza Garibaldi, where the views open up to the valley in a breathtaking panorama.
If you are looking for a longer walk, there is the option of continuing on foot from Acquaviva to Valiano, extending the walk until the final transfer to Cortona.
Overnight in Cortona
Hotel San Michele
Located in the former Baldelli Palace, one of the oldest buildings in Cortona, it offers restored spaces that retain their original features.
Its rooms have free Wi-Fi, television, air conditioning and private bathrooms.
*In case this accommodation is not available, you will stay in a similar category hotel.
Day 5 - Enjoy your day exploring the area around Cortona 6,1 miles | 9,8 km
You will start the morning with a short transfer to Ossaia, the starting point for the walk that will take you to the charming village of Tuoro, already in Umbrian territory. The trail crosses gentle hills and offers spectacular views of the Val di Chiana valley and Lake Trasimeno, whose waters sparkle in the background.
As you walk, you will pass through a setting steeped in history. Here, in 217 BC, the Battle of Lake Trasimeno took place, where Hannibal and his Carthaginian troops ambushed the Roman army in one of the most famous confrontations of the Second Punic War.
When you arrive in Tuoro, you can take a break in one of its cafés or explore its small shops, perfect for a drink or to pick up a local souvenir.
In the afternoon, a transfer will take you back to Cortona, where you will spend your second night. Take the opportunity to stroll around at your leisure, find a terrace with a view or simply let yourself be enveloped by the medieval magic that characterises this town suspended in time.
As you walk, you will pass through a setting steeped in history. Here, in 217 BC, the Battle of Lake Trasimeno took place, where Hannibal and his Carthaginian troops ambushed the Roman army in one of the most famous confrontations of the Second Punic War.
When you arrive in Tuoro, you can take a break in one of its cafés or explore its small shops, perfect for a drink or to pick up a local souvenir.
In the afternoon, a transfer will take you back to Cortona, where you will spend your second night. Take the opportunity to stroll around at your leisure, find a terrace with a view or simply let yourself be enveloped by the medieval magic that characterises this town suspended in time.
Overnight in Cortona
Hotel San Michele
Located in the former Baldelli Palace, one of the oldest buildings in Cortona, it offers restored spaces that retain their original features.
Its rooms have free Wi-Fi, television, air conditioning and private bathrooms.
*In case this accommodation is not available, you will stay in a similar category hotel.
Day 6 - Cortona to Solomeo 4,2 miles | 6,7 km
The day begins with a one-hour transfer included to the Sanctuary of the Virgin of Mongiovino, a Renaissance abbey hidden among the forests of Umbria. Before starting the walk, take a moment to visit this peaceful place of pilgrimage and, if you wish, visit Mongiovino Castle, which adds a medieval touch to the start of the day.
From here, you will begin a gentle climb on foot to Panicale, a charming medieval hilltop village offering sweeping views of Lake Trasimeno and the surrounding countryside. Access to the old town is easy, and once inside, you will discover a cosy square with a café perfect for enjoying a light lunch or a glass of local wine, surrounded by traditional architecture and a leisurely pace.
In the afternoon, a transfer included in the price will take you to Solomeo, where you will spend the night. This small restored village, known for its elegance and connection to art and craftsmanship, will be the perfect setting to continue your immersion in the most authentic Umbria.
From here, you will begin a gentle climb on foot to Panicale, a charming medieval hilltop village offering sweeping views of Lake Trasimeno and the surrounding countryside. Access to the old town is easy, and once inside, you will discover a cosy square with a café perfect for enjoying a light lunch or a glass of local wine, surrounded by traditional architecture and a leisurely pace.
In the afternoon, a transfer included in the price will take you to Solomeo, where you will spend the night. This small restored village, known for its elegance and connection to art and craftsmanship, will be the perfect setting to continue your immersion in the most authentic Umbria.
Overnight in Solomeo
Borgo Mandoletto
Located in the countryside of Solomeo, it combines a rural setting with classic décor. This accommodation offers rooms with free Wi-Fi, flat-screen TVs, air conditioning and private bathrooms.
It also has a beautiful, extensive garden and a restaurant serving local cuisine.
*In case this accommodation is not available, you will stay at a similar category one.
Day 7 - Enjoy your day exploring the area around Solomeo 8,3 miles | 13,4 km
The day begins with a transfer included to Cibottola Castle. Explore this ancient fortress with a 4,5 km stretch that winds through rolling hills and open fields, adding a touch of adventure and beauty to the day's itinerary.
Next, you will arrive at the Monte Vibiano Winery, where a unique experience awaits you. Take a tour of the vineyard by car or electric bike, followed by a wine tasting where you can sample some of the region's most representative varieties. The estate, a pioneer in sustainability, offers the perfect break to enjoy the landscape, wine and Umbrian agricultural tradition.
After the visit, you will continue walking towards Castiglione della Valle along a quiet, almost flat path that runs alongside the Nestore River Park. This final stretch offers a relaxed pace, ideal for savouring the natural surroundings after a morning of discovery.
At the end of the walk, a transfer included will take you back to Solomeo, where you can rest or take a stroll through this charming restored village.
Next, you will arrive at the Monte Vibiano Winery, where a unique experience awaits you. Take a tour of the vineyard by car or electric bike, followed by a wine tasting where you can sample some of the region's most representative varieties. The estate, a pioneer in sustainability, offers the perfect break to enjoy the landscape, wine and Umbrian agricultural tradition.
After the visit, you will continue walking towards Castiglione della Valle along a quiet, almost flat path that runs alongside the Nestore River Park. This final stretch offers a relaxed pace, ideal for savouring the natural surroundings after a morning of discovery.
At the end of the walk, a transfer included will take you back to Solomeo, where you can rest or take a stroll through this charming restored village.
Overnight in Solomeo
Borgo Mandoletto
Located in the countryside of Solomeo, it combines a rural setting with classic décor. This accommodation offers rooms with free Wi-Fi, flat-screen TVs, air conditioning and private bathrooms.
It also has a beautiful, extensive garden and a restaurant serving local cuisine.
*In case this accommodation is not available, you will stay at a similar category one.
Day 8 - Solomeo to Perugia 9,2 miles | 14,8 km
The day begins with a transfer included to Monte Tezio, crossing the rolling landscapes of Umbria until you reach this panoramic viewpoint. From here, you will begin a walk steeped in history, following ancient trails that supplied Perugia with drinking water in the Middle Ages. Along the way, sections of the old aqueducts are still preserved, witnesses to a past that blends with the present-day natural environment.
Today's walk will take you to Perugia, which will welcome you with its imposing Etruscan gate, a monumental entrance that heralds the cultural wealth of this ancient city. Crossed by the Tiber River and dominated by the elegant Palazzo dei Priori, the city offers a vibrant mix of history, art and everyday life.
Take the time to explore its characterful streets, visit the National Gallery of Umbria, lose yourself in its markets and shops, or simply enjoy a drink in one of its lively squares.
Today's walk will take you to Perugia, which will welcome you with its imposing Etruscan gate, a monumental entrance that heralds the cultural wealth of this ancient city. Crossed by the Tiber River and dominated by the elegant Palazzo dei Priori, the city offers a vibrant mix of history, art and everyday life.
Take the time to explore its characterful streets, visit the National Gallery of Umbria, lose yourself in its markets and shops, or simply enjoy a drink in one of its lively squares.
Overnight in Perugia
Hotel Fortuna
The Hotel Fortuna is located in a 14th-century building and is decorated with 16th-century frescoes. It offers comfortable rooms with all amenities, free Wi-Fi, air conditioning, and private bathrooms.
*In case this accommodation is not available, you will stay at a similar category one.
Day 9 - Perugia to Florence 3,7 miles | 6 km
Start the day by taking a direct train to Florence, passing through some of Italy's most photogenic landscapes on a journey of approximately two and a quarter hours.
You can check train timetables on the Trenitalia website. Remember to take your luggage with you on the train.
Known as the ‘Athens of the Middle Ages’, Florence is an open-air museum. You will have time to explore its wonders at your own pace and discover its main icons. You can admire the majestic Duomo with its unmistakable dome, tour the imposing Palazzo Vecchio, or visit the Accademia Gallery, where Michelangelo's famous David awaits you.
Florence is the perfect finishing touch to this journey through the heart of Italy, a place where art, history and beauty can be felt in every corner.
You can check train timetables on the Trenitalia website. Remember to take your luggage with you on the train.
Known as the ‘Athens of the Middle Ages’, Florence is an open-air museum. You will have time to explore its wonders at your own pace and discover its main icons. You can admire the majestic Duomo with its unmistakable dome, tour the imposing Palazzo Vecchio, or visit the Accademia Gallery, where Michelangelo's famous David awaits you.
Florence is the perfect finishing touch to this journey through the heart of Italy, a place where art, history and beauty can be felt in every corner.
Overnight in Florencia
Classic Hotel
This family-friendly accommodation is located in a fully restored 19th-century guest house surrounded by lush gardens and centuries-old trees.
This accommodation offers rooms with free Wi-Fi, flat-screen TVs, air conditioning and private bathrooms.
*In case this accommodation is not available, you will stay at a similar category one.
Day 10 - Florence
After a delicious breakfast, it will be time to say goodbye to these spectacular regions of Italy and fly back to your home city.
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Itinerary Map
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Services
Included
- Accommodation in en suite rooms
- Daily Breakfasts
- 2 Dinners
- Wine tasting at the Monte Vibiano Winery on day 7
- Luggage transfers between accommodations on days 4, 6 and 8
- Transfers as specified in the itinerary
- Information dossier with maps and routes
- 24-hour telephone support
- Sustainable travel, we compensate the CO2 emissions of your trip
- Taxes
Extras
- Travel insurance
- Cancellation insurance
- Additional nights
Accomodation
General information
The accommodations with which we collaborate have a private bathroom and all the necessary services to ensure the best comfort available.
Our team checks in situ the quality of all the accommodations offered, so that you have an unforgettable experience during your trip.
The accommodation that we will book for your trip will be selected taking into account our commitment to you: guaranteeing comfort, calm and enjoyment throughout your trip.
We work with quality hotels and country cottages with limited capacity, so we invite you to confirm your reservation as soon as possible.
The name of each accommodation will be provided to you a few weeks before your trip begins.
Room types
It is possible to book this journey in single, double or triple rooms.
All rooms have private bathrooms.
Travel & Transfers
To reach the starting point of this hiking trail, you can fly to Pisa, Florence or Rome airports. From Florence, take tram T2 and then a train to Siena city centre. You can find more information about the train on the Trenitalia website.
From Pisa, you can easily reach Siena by direct bus in two and a half hours with FlixBus. You also have the option of travelling by train, changing at Empoli. From Rome, although the journey takes almost four hours, you can travel to Siena on a direct FlixBus.
To return to your city of origin from Florence, you can fly from Pisa, Florence or Rome airports. Florence airport is just 15 minutes from the city centre and can be reached by bus lines 30 and 35 or tram line T2. If you are flying from Pisa airport, there is a direct train service.
You also have the option of flying from Rome, in which case you will need to take a train from Florence to Termini station and then take the Leonardo Express train to the airport.
You can find more information about trains on the Trenitalia website.
From Pisa, you can easily reach Siena by direct bus in two and a half hours with FlixBus. You also have the option of travelling by train, changing at Empoli. From Rome, although the journey takes almost four hours, you can travel to Siena on a direct FlixBus.
To return to your city of origin from Florence, you can fly from Pisa, Florence or Rome airports. Florence airport is just 15 minutes from the city centre and can be reached by bus lines 30 and 35 or tram line T2. If you are flying from Pisa airport, there is a direct train service.
You also have the option of flying from Rome, in which case you will need to take a train from Florence to Termini station and then take the Leonardo Express train to the airport.
You can find more information about trains on the Trenitalia website.
FAQs
Is luggage transfer included? What are the luggage requirements?
Absolutely! Each traveller has included 1 piece of luggage that we will transfer between your accommodations. It's important that this piece of luggage meets the following criterias:
- Maximum weight of 45 lbs (20 kg).
- Maximum dimensions 65x50x40 cm.
- Must be only 1 piece of luggage without any attachments or accessories.
- Should not contain valuables, fragile items, food or medications.
- Must be correctly identified (booking reference of your trip and the full name of the trip holder).
What is the best time of year to do this trip?
Springtime and the months of April, May, and June are absolutely enchanting. Autumn is a perfect time of year thanks to its mild temperatures, making September and October unmissable. July and August can get very hot, so we recommend starting your walks early to avoid the heat of the day. Please note that before Easter and at the end of October, some local shops and restaurants may have reduced opening hours or be closed for the winter.
What if I'm not able to finish one of the stages?
You can call us to arrange a private transfer for you.
If you prefer, you can also use public transport or local taxis to get to your next accommodation.
What should my physical preparation be?
This route is of medium-low difficulty, making it ideal for people looking for 4 to 6 hours of walking per day with climbs that can be steeper and longer. You do not need to have hiking experience, however, it is recommended that you are in good physical condition and in good health. Some sections of the walk have uneven terrain, including rocky areas.
How far in advance should I book my trip?
We suggest that you make the reservation as soon as possible, as soon as you have decided your travel dates, as this destination is very popular and bookings in accommodation are quickly taken up.
What equipment do I need to bring?
Once you make your reservation we will send you all the detailed information about the specific equipment you need for this route, considering recommendations for shoes, boots, clothes and a day-to day backpack.
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