Luxury Roadtripping in Tuscany

Italian cypress trees rows and a white road rural landscape. Siena, Tuscany, Italy, Europe.
Price From $2,790 pp
When to Go Apr, May, Jun, Jul, Aug, Sep
Luxury Roadtripping in Tuscany

“This itinerary takes you through idyllic countryside, down quiet country roads and past lush vineyards and olive groves. You’ll explore medieval villages and castles, sample fine wine at a Chianti winery, and soak up culture in the city of Siena and town of Pienza.”

Day 1

Day 1
Arrival Tuscany - Chianti

Upon arrival at the airport, you’ll be escorted by car to your accommodation, Borgo Scopeto, the former estate of a nobleman.

Enjoy lunch on the terrace with views across Siena before beginning your Tuscany road trip in a gleaming vintage car.

Today’s tour takes you through the olive groves and vineyards of Chianti, where you’ll see ancient castles, historic towns, grand palaces, and stop for a tasting in a renowned vineyard.

Day 2

Day 2
Tuscany: Pienza

Today’s journey takes you through the picturesque region of Crete Senesi, renowned for its exquisite landscapes, to Pienza. Designed by Pope Pius II as ‘an ideal Renaissance town’, you’ll be escorted by your private guide through the cobblestone alleys of this UNESCO site to visit the castle and Renaissance palaces.

Return to your accommodation via the medieval town of Montepulciano, passing lush vineyards, before enjoying dinner and a stroll in Siena.

Day 3

Day 3
Tuscany: Volterra

Your drive today takes you past villas, monasteries, medieval castles and more scenery. Visit the walled medieval hill town of San Gimignano, before reaching Volterra, an Etruscan city famed for its alabaster carvings.

Spend time exploring the old town and watching artisans at work, before driving back past vineyards and the Tuscan Ore Mountains to dine at a luxury villa overlooking Chianti.

Day 4

Day 4
Siena – Departure

Spend your final day in Tuscany exploring the city of Siena.

Enjoy a private guided tour of the city’s main artistic and architectural masterpieces, including the Gothic cathedral, before your chauffeur-driven journey to the airport for your onward travel.

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itinerary highlights
  • Stay in a magnificent country estate overlooking the city of Siena
  • Drive through Tuscany’s countryside in a classic vintage car
  • Go wine tasting in Chianti at one of the world’s oldest vineyards
  • Explore the medieval towns of San Gimignano, Montepulciano, Volterra and Siena
  • Discover the UNESCO World Heritage Site of Pienza, a Renaissance town
destinations in the itinerary
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