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 ambiance and relax into ‘la vita bella’.

On this slow-paced trip there are of course wonderful hikes 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 historic 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 center (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 partner. Montepulciano 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 doing the hike 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 (1,713ft/1,522ft)

Leaving Montepulciano, on a half-day hike 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 hike continuing from Acquaviva to Valiano and then transferring from there to Cortona.

Cortona, located at 600m/1,968ft altitude, is characterized 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 Hike: 9km (6 mi). Ascent/Descent: 37m/269m (121ft/883ft)

Acquaviva to Valiano Walk: 7km (4.5mi). Ascent/Descent: 3m/49m (10ft/161ft)

Combined Hike: 16km (10.5mi). Ascent/Descent: 40m/318m (131ft/1,043ft)

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

Cross 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 (1,007ft/1,070ft)

Today begins with a transfer (1hr) to the Mongiovino Abbey – ‘Madonna di Mongiovino Sanctuary’ at 0900am. From here the hike 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, which 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 (748ft/407ft)

There’s an included transfer to Cibottola Castle (taking around 10 minutes) or alternatively to Monte Vibiano Winery (approx. 20 minute 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 hike to the vineyard is an additional 4.5km/3mi, making the total hike 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 Hike: 4.5km (3mi). Ascent/Descent: 3m/265m (10ft/869ft)

Monte Vibiano Winery to Castiglione della Valle Hike: 8.5km (5.2 mi). Ascent/Descent: 70m/70m (230ft/230ft)

Combined Hike: 13km (8mi). Ascent/Descent: 73m/335m (240ft/1,099ft)

Please note that the Monte Vibiano Winery is currently closed until further notice For those travelling in 2026, the itinerary will be changed.

The day will instead include a visit to Cantina Berioli Winery, along with a scenic 6.3 km (3.9mi) walk offering panoramic views across Lake Trasimeno and the valley towards Perugia, with Assisi visible in the distance on particularly clear days.

After an early transfer to Monte Tezio at 0830am (approx. 40 minute drive) the hike 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 travelers 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 also 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 hike. The distances shown are based on the shorter route. This hike 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, hike from there into the city center. By taking this transfer it shortens the route which is a trickier hilly section on asphalt. If preferred, then the hike directly into the city is possible (without the transfer).

Monte Tezio to San Marco (Part 1): 13.5km (8.5mi). Ascent/Descent: 218m/330m (715ft/1,083ft)

Monte Ripido Convent to Perugia (Part 2): 2km (1.5mi). Ascent/Descent: 32m/44m (105ft/144ft)

Combined Hike: 15.5km (9.5mi). Ascent/Descent: 250m/374m (820ft/1,227ft)