Day 1 – Siena: Art & Tradition

Spend the day exploring Siena’s historic centre. Stroll through Piazza del Campo, visit the Cathedral and discover the medieval streets winding between historic palaces and traditional shops.

Day 2 – Crete Senesi & Asciano: The Tuscan Countryside

Explore the landscapes surrounding Sosta Eroica. With their clay hills, white gravel roads and sweeping views, the Crete Senesi offer some of the most distinctive scenery in Tuscany. 

Day 3 – Val d’Orcia: Historic Villages & Scenic Views

Spend the day exploring the Val d’Orcia, renowned for its iconic landscapes and charming historic villages. 

Seven days is the perfect amount of time to discover Tuscany at a relaxed pace, combining art cities, medieval villages, wine tastings and unforgettable landscapes. Staying at Sosta Eroica in Asciano, you can explore the rolling hills of the Crete Senesi and discover some of the region’s most beautiful destinations, returning each evening to the peace and quiet of the Tuscan countryside.

Day 1 – Siena: Art, History & Local Flavours

Begin your journey in Siena, wandering through its medieval streets towards Piazza del Campo and the magnificent Cathedral.

Day 2 – Crete Senesi: Tuscany at Its Most Authentic

Spend the day discovering the landscapes surrounding Sosta Eroica. With their distinctive clay hills, winding white gravel roads and sweeping horizons, the Crete Senesi offer a striking alternative to Tuscany’s classic vineyard scenery.

Day 3 – Chianti: Vineyards, Hilltop Villages & Wine Tastings

Spend the day exploring Chianti, a landscape of vineyard-covered hills, charming stone villages and scenic country roads.

Day 4 – Montalcino: Discover the Home of Brunello

Head to Montalcino, the hilltop town renowned worldwide for its Brunello wine. Wander through the historic centre, visit the fortress and browse the wine shops and local boutiques that celebrate the area’s rich winemaking heritage.

Day 5 – Montepulciano: Renaissance Charm & Vino Nobile

Continue to Montepulciano, with its uphill historic streets, elegant Renaissance palaces and beautiful Piazza Grande.

Day 6 – Val d’Orcia: Picture-Perfect Villages

Spend the day exploring the Val d’Orcia, one of Tuscany’s most iconic landscapes.

Day 7 – Choose Your Own Tuscan Experience

After a week of exploring cities, villages and wineries, leave your final day free to enjoy whatever you love most. Embrace the outdoors or treat yourself to a memorable food and wine experience.

Here are a few ideas:

• Cycling: follow the white gravel roads of the Crete Senesi and discover the landscapes that make the Eroica cycling routes so special.

• Nature: enjoy a scenic walk through the rolling hills around Asciano.

• History & Culture: visit a historic abbey or explore another village that catches your eye. We particularly recommend Monte Oliveto Maggiore Abbey, renowned for its beautiful setting and remarkable Renaissance frescoes.

• Food & Wine: enjoy a tasting of local products or arrange a food and wine experience to discover the flavours and traditions of Tuscany.

Our tip: don’t try to fill every moment of your trip. Leave room for an unplanned stop, a beautiful view worth photographing or a long, leisurely lunch. Often, these are the moments you remember most fondly.