Trails of Tuscany & Umbria

Arriving in the medieval city of Siena gives the feeling of having stepped back in time. At Siena’s heart is Il Campo; the central piazza and where the Palio horse race takes place twice every summer. After checking in at the hotel, why not head here for a coffee or glass of chilled wine and soak up the Italian ambience and relax into ‘la vita bella’.

On this slow-paced trip there are of course wonderful walks to take in the stunning Tuscan and Umbrian rolling hills, sprawling olive groves and vineyards, but also time to explore the iconic towns at your own pace. You have this afternoon and tomorrow morning free, so we recommend arriving early today to make the most of this first stop in the historical town of Siena.

Siena is a UNESCO World Heritage Site and one of Italy’s must-see attractions. The city is well-known for its wine and cuisine, art, museums, and Gothic architecture. Take time this morning to discover this charming historic town.

Why not add on the "Taste of Siena Food Tour" so you can eat your way through Siena’s hidden corners? Sample tastings of traditional delicacies, local wines, handmade pasta, olive oil and cheese as you walk through the historic centre (tour duration: 3 hrs, 10am start).

This afternoon, take the train (payable locally, approximately 1 hour duration) on a picturesque journey through classic Italian landscapes to Montepulciano. From the train station there is an included transfer to the hotel, where there will be a welcome meeting with our local supplier. The town is known for its red wine ‘Vino Nobile’, so perhaps relax with a glass this evening or purchase a bottle or two to bring home.

This morning starts with an included transfer to Pienza at 0900am. Pienza is said to boast the most delicious pecorino cheese in the whole of Tuscany—why not stop in at one of the shops and get some to take home? This UNESCO World Heritage town was commissioned by the pope in 1459 to the architect Bernardo Rossellino, with the task of designing the perfect town. Parts of the town were used in the filming of ‘The English Patient’, which was largely set in the nearby Sant’ Anna Monastery. Don’t miss taking a short walk along the wall on the south edge of town to take in the panoramic view.

On the walk back to Montepulciano it’s possible to visit one of the quaint cafes or stop for a picnic lunch in Monticchiello, a stunning hamlet with fortified walls.

Alternatively, instead of joining the walk today, there’s the option of relaxing and exploring the town of Montepulciano. The Church of Sant’Agostino is worth a visit as is the Palazzo Comunale, where it’s possible to climb the tall tower to get a view of the surrounding countryside. The historic Caffe’ Poliziano is an ideal lunch spot. Take a wander around the main square of Piazza Grande and the nearby Fortress of Montepulciano with its delightful gardens.

Ascent/Descent: 522m/464m

Leaving Montepulciano, on a half-day walk through the iconic Tuscan countryside of yellow fields and hilltop villages to Acquaviva. From here a transfer is included to Cortona at 1pm, where it’s easy to find a quiet spot to relax in the Tuscan sun and read a good book or enjoy watching the world go by.

Alternatively, there is the option to do a longer full-day walk continuing from Acquaviva to Valiano and then transferring from here to Cortona. 

Cortona, located at 600m altitude, is characterised by steep narrow streets and medieval architecture. Pay a visit to the distinguished Etruscan Academy Museum, founded in 1727, or simply enjoy the expansive views from the Piazza Garibaldi.

Montepulciano to Acquaviva: 9km (6 mi). Ascent/Descent: 37m/269m
Acquaviva to Valiano: 7km (4.5mi). Ascent/Descent: 3m/49m
Combined: 16km (10mi). Ascent/Descent: 40m/318m

The day begins with a short (10-minute) transfer to Ossaia at 0900am, which is the starting point for the walk to Tuoro. The walk provides spectacular views over the Valdichiana Valley and Lake Trasimeno. This historical location is where Hannibal’s Carthaginian warriors ambushed the Roman Army in 217 BC at the Battle of Lake Trasimeno.

Crossing into Umbria at the village of Tuoro, where there are several lovely shops and a café to quench your thirst. A transfer (20 minutes) will be provided back to the village of Cortona for a second night.

Ascent/Descent: 307m/326m

Today begins with a transfer (1h) to the Mongiovino Abbey – ‘Madonna di Mongiovino Sanctuary’ at 0900am. From here the walk commences to the charming medieval hilltop village of Panicale. Before setting out, pay a visit to the Renaissance-era abbey and follow the path up to also visit Mongiovino Castle.

It’s easy terrain to Panicale and there’s the chance to take a short detour to the peaceful little Lupaia Lake along the way.  This is an additional 2.3km/1.4mi, making the overall walk 9.1km/5.7mi.

Panicale has a nice square with a café where it’s possible to enjoy a light lunch and a glass of local wine. From Panicale there is an included transfer to the accommodation in the afternoon, which takes around 30 minutes. The next 2-nights will be in Solomeo.

Mongiovino Abbey to Panicale: 7km (4mi). Ascent/Descent: 228m/124m
Mongiovino Abbey to Panicale with detour to Lupaia Lake: 9km (5.5 mi). Ascent/Descent: 324m/219m

There’s an included transfer to Cibottola Castle (taking around 10 minutes) or alternatively to Monte Vibiano Winery (approximately 20 minutes’ drive) at 0830am. If the chosen drop-off point is Cibottola Castle, then there’s the chance to visit here before walking to the winery. The walk to the vineyard is an additional 4.5km/3mi, making the total walk today 13km/8mi.

At Monte Vibiano Winery there’s an included tour of the vineyard by electric car or e-bike and a wine tasting to sample the local varieties.

The walk from the winery to Castiglione della Valle is a peaceful and relaxing stretch, along an almost-flat path, which traces the Nestore River Park. At the end of the walk there is a transfer back to your accommodation in Solomeo. 

Cibottola Castle to Monte Vibiano Winery: 4.5km (3mi). Ascent/Descent: 3m/265m
Monte Vibiano Winery to Castiglione della Valle: 8.5km (5.2 mi). Ascent/Descent: 70m/70m
Combined: 13km (8mi). Ascent/Descent: 73m/335m

After an early transfer to Monte Tezio at 0830am (approximately 40 minutes’ drive) the walk begins to Perugia along a historic route. It goes through the Tezio area—an important location in the Middle Ages as it was the source of drinking water for the city. It is still possible to see remnants of the ancient aqueducts.

Perugia’s huge Etruscan arch gate welcomes travellers to the capital of Umbria. Crossed by the River Tiber, Perugia is home to the Palazzo dei Priori, which looms above the main piazza. The city is home to some of the best museums in Umbria, including the Galleria Nazionale dell’ Umbria. There’s also the chance to wander through the markets, shops, and arcades of this enchanting city.

There are two options for today’s walk. The distances shown are based on the shorter walking route. This walk goes from Mount Tezio to San Marco village, just outside Perugia. There’s then a short 10-minute transfer to the Monte Ripido Convent at the entrance to Perugia. After time to visit the convent, walk from there into the city centre. By taking this transfer it shortens the route which is a trickier hilly section on asphalt. If preferred, then the walk directly into the city is possible (without the transfer).

Monte Tezio to San Marco (Part 1): 13.5km (8.5mi). Ascent/Descent: 218m/330m
Monte Ripido Convent to Perugia (Part 2): 2km (1.5mi). Ascent/Descent: 32m/44m
Combined: 15.5km (9.5mi). Ascent/Descent: 250m/374m

Feel like a local and discover the food and wine scene of Perugia by booking an additional experience called the "Taste of Perugia Food Tour" (duration: 3,5 to 4 hrs, 10am start). Then catch a direct train, speeding through photogenic Italian landscapes, to Florence’s Santa Maria Novella Station (takes approximately 2 hours 15, payable locally). Or if you prefer, you could get an early train to Florence. 

Upon arrival in Florence, known as ‘The Athens of the Middle Ages’, there is then time at leisure to explore this incredible historic city. Immerse yourself in the wonders of Florence there is the option of doing a circular walking loop taking in Florence’s top attractions. Discover Palazzo Vecchio, the infamous fortress, and Florence Town Hall, navigate Accademia Galleria for Michelangelo’s “David,” and be awed by the huge exterior of Florence’s Cathedral “Duomo.”

Ascent/Descent: 114m/114m

From Florence it’s easy to take a day trip to Pisa as it is only an hour’s journey between the two cities (please contact us if you would like to add a night here).

Check out of the hotel and continue with onward journey.