Private Luxury Tour of Cortona & Montepulciano

Private Luxury Tour of Cortona & Montepulciano – Val d’Orcia, Tuscany

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Explore the hilltop villages of Cortona & Montepulciano
Optional visit to Pienza, home of pecorino cheese
Wine and food traditions of Val d’Orcia
Private driver and expert local guide included

An Exclusive Hilltop Journey through the Timeless Charm of Val d’Orcia, Tuscany

Discover two of Tuscany’s most romantic medieval towns on this private luxury tour through Cortona and Montepulciano, located in the iconic Val d’Orcia area, a UNESCO World Heritage site in southern Tuscany. With endless rolling hills, ancient cypress-lined roads, and sweeping vineyard views, this experience combines history, elegance, and artisan traditions.

Guided by a local expert, you’ll wander through cobbled streets, discover hidden artisan shops, and enjoy panoramic views that once inspired Renaissance painters. The tour can be customized to include Pienza, renowned for its pecorino cheese, Renaissance architecture, and postcard-worthy vistas — perfect for a complete slow luxury escape in the Tuscan countryside.

Have questions?

Schedule a call with our team! A dedicated advisor will contact you to provide all the necessary details and information about this home and how to plan your tailor-made holiday.

Join us for a truly exclusive culinary experience where the flavors of Tuscany, the prestige of Brunello wines, and the beauty of the countryside come together to create memories that will last a lifetime.

Your Questions Answered

What will we experience in Cortona and Montepulciano?

Your day centers on exploring Cortona and Montepulciano with a local expert, including cobbled-street walks, hidden artisan shops, and panoramic views. A private driver and expert local guide support the journey through these hilltop towns.

Can we add a visit to Pienza and its pecorino traditions?

Pienza can be added as an optional visit, bringing Renaissance architecture, postcard-worthy vistas, and the area’s pecorino cheese tradition into the itinerary. Please share if you would like this customization, which can be requested subject to availability.

Are admissions to attractions included in the tour?

A private driver and expert local guide are included in the experience. If you are considering entry to attractions in Cortona, Montepulciano, or optional Pienza, please ask us to confirm whether admissions are covered.

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