Italy
Tuscany
Where every curve tells a story.
Tuscany is the original driving landscape. Cypress-lined roads climb through Chianti vineyards. Medieval hilltop towns appear around every bend. The Via Chiantigiana and the roads of Val d’Orcia have inspired drivers for generations.
Stays are restored estates and monasteries chosen for architecture and quiet — the kind of property where the view from the room matters more than the size of the lobby. Once your vehicle tier is set, the car is staged for handoff in Florence, with delivery and return timed to your itinerary.
Journey Highlights
What Defines It
Roads That Reward
The SR222 Chiantigiana, the cypress spirals of Val d’Orcia, the Crete Senesi backroads. Routes personally scouted for driving quality, not just scenery.
Design-Forward Stays
Restored monasteries with vineyard views. Boutique properties where architecture matters, chosen for soul rather than scale.
One Experience Daily
Private winery visit with the family who makes the wine. Truffle hunting with a tartufaio and his dogs. Dinner at a restaurant worth booking months ahead.
Unhurried Pace
2–3 hours of driving per day. Many stops. No forced schedules.
Photo Locations Mapped
Cappella di Vitaleta at golden hour. The La Foce zigzag road. Podere Belvedere at dawn. GPS coordinates and optimal timing in your roadbook.
Direct Support
Support available throughout your journey. Restaurant needs changing? We handle it — this is personal service, not an app.
5 Nights · 4 Driving Days
The Itinerary
Designed around one philosophy: drive beautiful roads, stop often, arrive properly.
Arrival
Settle in, breathe, arrive properly
Pick up your car in Florence. We route you through the Chianti foothills immediately — terracotta rooftops and olive groves within minutes of leaving the city.
The Chianti Classico Loop
The iconic Tuscan driving day
This is the drive that defines Chianti. The road through Black Rooster territory, vineyards stretching in every direction.
Radda to Panzano
Deeper into Chianti
A quieter side of Chianti. The SP2bis spirals through vineyards and ancient woods between Radda and Panzano — a slower, more technical road than the Chiantigiana, rewarding a patient pace. A private tasting at Castello di Volpaia in Radda, then lunch at Antica Macelleria Cecchini in Panzano.
Siena & the Crete Senesi
Medieval grandeur meets lunar landscapes
Morning in Siena. Afternoon through the Crete Senesi, the lunar clay hills unlike any other part of Tuscany.
Val d’Orcia & Montalcino
South into the UNESCO landscape
South on the SP146 through the Val d’Orcia — cypress-lined straights, the Vitaleta Chapel, golden hills toward Montalcino and its Brunello country. A private tasting and lunch at Castello Banfi, the estate that put Montalcino on the map.
Departure
A proper ending
No rushed checkout. Breakfast at the hotel, a final walk through the property, then the scenic route back to Florence.
The Routes
Driving Profile
Tuscany’s roads were made for driving. The terrain constantly varies — long vineyard straights, tight village approaches, sweeping elevation changes through the hills.
SR222 Via Chiantigiana
70 kmThe iconic Florence-Siena route through Chianti Classico. Vineyards, olive groves, and medieval villages at every turn.
SP2bis Radda to Panzano
25 kmA spiraling secondary road through vineyards and ancient woods. Rewards smooth inputs and a patient pace.
SP146 Val d’Orcia
50 kmThe UNESCO landscape. Cypress-lined roads, the Vitaleta Chapel, endless golden hills stretching to the horizon.
SS438 Crete Senesi
40 kmClay hills and lunar landscapes unlike anywhere else in the region.
From the Driver’s Seat
The Chiantigiana
The Machine
Vehicle Options
The car is the point. We arrange vehicles that match the legendary Italian roads.
- Performance: Alfa Romeo Giulia Quadrifoglio · BMW M3/M4
- Performance+: Porsche 911 Carrera · Porsche 911 Targa 4 GTS · Audi R8
- Grand Touring: Porsche Taycan Cross Turismo · Aston Martin DB11 · Bentley Continental GT
- Hyper: Ferrari Roma · Lamborghini Huracán · McLaren GT
The Details
What’s Included
Everything arranged so you can focus on the drive.
From US$7,000 per person (approx. €6,300)
Two guests sharing a vehicle and a double or twin room · US$14,000 total for two
Single occupancy from US$12,000
Base price reflects shoulder-season travel with a Performance-tier vehicle. Peak dates, higher vehicle tiers, added nights, and expanded experiences are priced in your proposal.
Vehicle & Logistics
Vehicle arranged (tier selected during planning), car delivery and pickup in Florence, rental insurance included, toll transponder included.
Accommodations & Dining
5 nights in premium accommodation, daily breakfast, key dinner reservations arranged, private winery visit with tasting and lunch — one anchor experience per day.
Planning & Support
Curated day-by-day driving itinerary, ZTL zone guidance (avoid traffic fines), support available throughout your journey, restaurant changes handled if needed.
Begin Planning
Engagement begins with a private consultation to understand what matters most for your journey.
Request ConsultationTraveling as two? See our luxury driving tours for couples →