TUSCANY

Southern Tuscany: Cortona and Pienza - a Tuscan Lands exclusive tour

Highlights

This is a day to slow down and truly see Tuscany — not just through the places you visit, but through how you’re welcomed, what you taste, and the time you’re given to enjoy it all.
The journey begins in Cortona, a hilltop town filled with quiet stone alleys and long views over the Val di Chiana. Before entering the town, there’s a brief stop in front of the private villa featured in Under the Tuscan Sun — a quiet nod to a story that made many dream of Tuscany. Then, time to explore the center at your own pace.
Before lunchtime, you’ll travel toward Val d’Orcia, where a table awaits in a restored farmhouse surrounded by vineyards and olive trees. The setting is peaceful and unhurried. Lunch is long, seasonal, and deeply tied to the land.
After lunch, the day continues to Pienza, known for its harmony, golden light and small-town charm. Whether you visit a cheese shop or simply take in the views, the atmosphere lingers. Everything is arranged — so you can focus on what’s in front of you. And if there’s something you'd like to include, we’ll take care of the details.

About your Experience

Ideal for:

Travelers who enjoy quiet towns, countryside landscapes, and meaningful moments. Ideal for families or friends looking to enjoy a curated day with beautiful scenery and no rush.

Important to Know:

• Although this is a private experience, we suggest minimum of 4 participants.
• Fully customizable itinerary — let us know if there’s a specific place you wish to include.

Available Options:

Full Experience with private driver from Florence or from your hotel in Tuscany or Umbria.

Available in English and Portuguese, upon availability.

Where:

Cortona, 1h30 from Florence and Pienza, 1h45 from Florence.

When:

Available all year. Advance booking required.

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