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Italy
Tuscany
Where every curve tells a story.
Trip Length3 or 5 Nights
Driving Days2–4 Days
Start & EndFlorence, Italy
Italy
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.
Accommodations are arranged at design-forward properties selected for location, character, and service — not for opulent lobbies. Vehicle selection is handled during planning: once your tier is set, the car is staged for handoff in Florence with delivery and return coordinated around your itinerary.
Journey Highlights
The SR222 Chiantigiana, the cypress spirals of Val d'Orcia, the Crete Senesi backroads. Routes personally scouted for driving quality, not just scenery.
Restored monasteries with vineyard views. Boutique properties where architecture matters. Not grand hotels with chandeliers — places with soul.
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.
2–3 hours of driving per day. Many stops. No forced schedules. The Seren Mont vibe: we take it slow and do things right.
Cappella di Vitaleta at golden hour. The La Foce zigzag road. Podere Belvedere at dawn. GPS coordinates and optimal timing in your roadbook.
Questions during your trip? Call us. Restaurant needs changing? We handle it. This is personal service, not an app.
4 Days · 2 Driving Days (or 6 Days · 4 Driving Days)
Designed around one philosophy: drive beautiful roads, stop often, arrive properly.
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 iconic Tuscan driving day
This is the drive that defines Chianti. The road through Black Rooster territory, vineyards stretching in every direction.
Medieval grandeur meets lunar landscapes
Morning in Siena. Afternoon through the Crete Senesi, the lunar clay hills unlike any other part of Tuscany.
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
Tuscany's roads were made for driving. The terrain constantly varies — long vineyard straights, tight village approaches, sweeping elevation changes through the hills.
The iconic Florence-Siena route through Chianti Classico. Vineyards, olive groves, and medieval villages at every turn.
A spiraling secondary road through vineyards and ancient woods. Rewards smooth inputs and a patient pace.
The UNESCO landscape. Cypress-lined roads, the Vitaleta Chapel, endless golden hills stretching to the horizon.
Clay hills and lunar landscapes. Lonely Planet called it the prettiest drive in Central Tuscany.
From the Driver's Seat
The Machine
The car is the point. We arrange vehicles that match the legendary Italian roads.
The Details
Everything arranged so you can focus on the drive.
From US$7,500 per couple (€6,750 approx.)
5-night version: +2 nights, priced in your proposal.
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 arranged (tier selected during planning), car delivery and pickup in Florence, full insurance coverage, toll transponder included.
3 or 5 nights in premium accommodation, daily breakfast at hotel, key dinner reservations arranged, private winery visit with tasting and lunch.
Curated day-by-day driving itinerary, ZTL zone guidance (avoid traffic fines), on-call support during travel, restaurant changes handled if needed.
Engagement begins with a private consultation to understand what matters most for your journey.
Request Consultation