Day 1: Arrive in Siena

Arrive in the medieval city of Siena, where you will feel as if you are stepping 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 your hotel, head here for a coffee or glass of chilled wine and let yourself soak up the Italian ambience and relax into ‘la vita bella’.

UPGRADE LODGING: Superior room in a 4* hotel in the city centre
UPGRADE EXPERIENCES: Join our "Taste Siena" food tour, a different way to visit this town, discovering its history, food and traditions. (Optional)

Free time in Siena

Day 2: Travel to Montepulciano

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 explore this charming historic town. This afternoon, take the train (payable locally, approx.1hr duration) on a picturesque journey through classic Italian landscapes to Montepulciano, from where you will receive a transfer to your hotel, for your welcome meeting.

UPGRADE LODGING: A charming suite in a BB in the city centre
UPGRADE EXPERIENCES: Wine tasting in a historic winery in the city centre

Choice of loop walks

Day 3: Montefollonico or Pienza and Montichiello

Option 1: Transfer to Montefollonico, an amazing village with terrific views over the Valdichiana. Take a relaxing stroll through vineyards and olive groves.
Walking distance: 14 km (3h30)
Option 2: Transfer to Pienza, a village said to boast the most delicious pecorino in the whole of Tuscany—why not stop in at one of the shops and take some home! On your return walk to Montepulciano you will come across Montichiello, a stunning hamlet with fortified walls.
Montichiello is the ideal spot to rest and enjoy a lovely lunch.
Walking distance:15 km (4-4h30)

UPGRADE LODGING: Second night in your suite in Montepulciano

Day 4: Half day walk to Acquaviva. Transfer to Cortona

Leaving Montepulciano, walk a short distance through the iconic Tuscan countryside of yellow fields and hilltop villages to Acquaviva. At around 12h30-13h00 take a transfer to Cortona, where you can find a quiet spot and relax in the Tuscan sun or perhaps a shady place. Cortona, located at 600m 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.

UPGRADE LODGING: Spend the night in a 4-star hotel in the city centre
UPGRADE EXPERIENCES: Visit the Etruscan Museum in town

Day 5: Ossaia - Tuoro. Transfer to Castel Rigone

Your day begins with a short (10 mins) transfer to Ossaia, where you start your walk to Tuoro. You’ll be walking with spectacular views over the Valdichiana Valley and Lake Trasimeno, scene of Hannibal’s ambush of the Roman Army in 217 BC (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 will take you onwards (20 mins) to the medieval village of Castel Rigone, with its late 15th-century church.

UPGRADE LODGING: Superior room in a Relais in Castel Rigone

Day 6: Panicale and Mongiovino Abbey & Castle

A 30 mins transfer brings you to Castello di Mongiovino, from where you will walk to the charming hill-town of Panicale. Before you set out, pay a visit to the Renaissance Mongiovino Abbey, before following the path up to the castle. Its easy terrain to Panicale; a picturesque medieval village with a nice square and café where you can enjoy a light lunch and a glass of good local wine. At 14h00 approx. take a transfer (30 mins) to your accommodation at la Corte del Poggio, a highlight of your Italian adventure.

UPGRADE EXPERIENCES: Cooking Class with dinner at Corte del Poggio

Day 7: Monte Vibiano and wine tasting

A car will transfer you to Monte Vibiano (20 mins) where you will visit the vineyards (touring by electric car) and enjoy the delights of the region with a wine tasting. Return on foot to your accommodation at La Carte del Poggio—a peaceful and relaxing stretch along an almost-flat path which traces the Nestore River Park.

UPGRADE LODGING: A charming suite in a BB in the city centre
UPGRADE EXPERIENCES: Wine tasting in a historic winery in the city centre

Day 8: Visit and taste Perugia

Spend one full day in the capital of Umbria. Discover the town in a different way with the Taste Perugia food tour.

UPGRADE LODGING: Night in a 5-star hotel in the city centre
UPGRADE EXPERIENCES: Taste Perugia Food Tour (optional)

Day 9: Visit Florence

Visit Florence and ask our team some guided tour or entrance to the museums, we are at your disposal.

UPGRADE LODGING: Night in a 5-star boutique hotel close to the Duomo and the SMN train station