Tuscany (Florence & Val d'Orcia) 🍷
"Renaissance art meets the golden cypress-lined roads of the Italian countryside."
Start in Florence for world-class Renaissance history before renting a luxury convertible. Drive through the Val d'Orcia to visit medieval hill towns like Pienza and Montalcino, staying in high-end vineyard estates.
A high-speed blend of world-class Renaissance art in Florence and a breathtaking road trip through the rolling cypress-lined hills of the Val d'Orcia.
Day-by-day itinerary
Day 1 · Renaissance Wonders of Florence
Morning — Start in the heart of Florence at the Piazza del Duomo. Marvel at Brunelleschi’s Dome and the Giotto’s Bell Tower. Walk to the Piazza della Signoria to see the open-air sculpture gallery.
Afternoon — Walk across the Ponte Vecchio to the Oltrarno district. Visit the Pitti Palace and climb the Boboli Gardens for a panoramic view of the Florentine skyline.
Evening — Enjoy an authentic Bistecca alla Fiorentina at a local trattoria in Santo Spirito, followed by gelato at Gelateria La Carraia.
💡 Book Uffizi Gallery tickets weeks in advance to avoid 3-hour queues.
Day 2 · The Scenic Drive to Siena
Morning — Say goodbye to the city and drive through the Chianti hills. Stop in the medieval walled town of Monteriggioni for a quick walk along the ramparts.
Afternoon — Pick up your rental car and drive to Siena. Explore the shell-shaped Piazza del Campo and the stunning zebra-striped Duomo di Siena.
Evening — Drive south into the heart of Val d'Orcia. Check into a luxury Agriturismo near Pienza and dine on handmade Pici pasta paired with local wine.
💡 Ensure your rental car has a GPS; cell service can be spotty in the rolling hills.
Day 3 · Postcard Views of Val d'Orcia
Morning — Explore the 'Ideal City' of Pienza, a UNESCO site. Walk along the city walls overlooking the Orcia Valley and visit the Palazzo Piccolomini.
Afternoon — Drive the iconic 'Gladiator Road' (near podere Terrapille) for photos of cypress-lined curves. Continue to Montalcino to sample world-famous Brunello wine.
Evening — Return to Pienza for a final sunset over the valley. Enjoy a cheese tasting of local Pecorino di Pienza before a quiet farewell dinner.
💡 The Chapel of Madonna di Vitaleta is most beautiful at sunrise if you can wake up early.