Private Transfer Florence to Cortona & Val di Chiana

A fully private chauffeur-driven transfer from Florence to Cortona — through the Val di Chiana, with optional stops at The Mall, Space Outlet, Valdichiana Outlet, Arezzo, Castiglion Fiorentino, Lucignano and Monte San Savino.

🚘 Florence → Cortona · private transfer 🛍 Optional: The Mall & Space Outlet 🏛 Optional: Arezzo & Piazza Grande 🏰 Optional: Castiglion Fiorentino 💍 Optional: Lucignano 📍 Pickup from your address
Private Transfer — Florence to Cortona & Val di Chiana

The Road to Cortona. One of the Great Drives in Tuscany.

Through the Val di Chiana, past outlets and medieval hill towns — to one of the oldest cities in Italy.

There is a moment, somewhere south of Florence on the old road through the Val di Chiana, when Tuscany reveals itself completely. The plain opens up below you, the lake of Trasimeno glints in the distance, and high on a ridge above everything else — Cortona. One of the oldest hilltop towns in Italy, built by the Etruscans long before Rome existed, looking out over a landscape that has barely changed in two thousand years.

Your private Mercedes driver picks you up directly from your hotel, villa, B&B or agriturismo anywhere in Florence and the surrounding area. No station, no shuttle bus, no luggage trolleys across cobblestones. We come to your address, load your bags, and take you directly to your destination in Cortona — whether that's a hotel on the main corso, a farmhouse on the hillside, or a private villa with a view over the Val di Chiana.

The drive takes approximately 1 hour 45 minutes by the direct route. But the Val di Chiana is one of the most rewarding stretches of Tuscany to travel through slowly — and a private transfer means the road is yours to shape. The valley is home to some of the best outlet shopping in Italy at The Mall Valdichiana, Space Outlet and the Valdichiana Outlet Village. It also passes within minutes of Arezzo — one of the most undervisited great cities of Tuscany, famous for Piero della Francesca's frescoes and its spectacular Piazza Grande. And between Florence and Cortona, a series of medieval hill towns — Castiglion Fiorentino, Monte San Savino, Lucignano — each one a perfectly preserved world of its own.

Tell us which stops interest you and we'll build the itinerary around your schedule. One stop or four — the driver is yours for the journey.

Cortona is not easy to reach by public transport. A private transfer is not just more comfortable — it's often the only practical way to get there directly from Florence with your luggage, at the time you want, to the exact address you need.

🚘
Door-to-door
Pickup from any hotel, villa or B&B in Florence — delivered to your exact address in Cortona.
~1h 45min direct
Direct transfer or longer with optional stops — the schedule is entirely yours.
🛍
Outlet shopping
The Mall Valdichiana, Space Outlet and Valdichiana Outlet Village — all on the road to Cortona.
🏛
Medieval hill towns
Arezzo, Castiglion Fiorentino, Lucignano, Monte San Savino — add one or more along the way.
Your Journey — Step by Step

Your Route, Your Stops

A direct transfer or a journey through the Val di Chiana with stops along the way. Every itinerary is confirmed in advance — tell us what you want and we'll plan accordingly.

Departure
Your address
Pick-up

Your Address in Florence

Your driver arrives at your hotel, villa, B&B or agriturismo at the agreed time. Luggage loaded, route confirmed — departure on schedule. Pickup available from Florence city centre, Fiesole, the Florentine hills and all surrounding addresses.

🚘 Heading south-east toward the Val di Chiana
Optional
+40 min
Optional Stop

Outlet Shopping — The Mall, Space & Valdichiana

Three of Italy's best outlet destinations grouped together in the Val di Chiana. The Mall Valdichiana — Gucci, Prada, Bottega Veneta, Valentino. Space Outlet — Prada and Miu Miu at factory prices. Valdichiana Outlet Village — over 130 brands in a pedestrian village format. Choose one or combine all three. Add 1–4 hours depending on your plans.

🚘 Through the Val di Chiana toward Arezzo
Optional
+1h from Florence
Optional Stop

Arezzo

One of the great undervisited cities of Tuscany. The Basilica di San Francesco with Piero della Francesca's cycle of frescoes — among the most important paintings of the Italian Renaissance. The Piazza Grande, sloping and asymmetric, is one of the most scenographic squares in Italy. Add 1.5–2 hours.

🚘 South through the valley — Castiglion Fiorentino
Optional
Val di Chiana
Optional Stop

Castiglion Fiorentino

A compact medieval borgo on a hilltop between Arezzo and Cortona. Famous for the Logge del Vasari and the panoramic view from the Torre del Cassero — a 360-degree sweep over the Val di Chiana. Add 45–60 minutes.

🚘 A few kilometres south — Lucignano
Optional
Val di Chiana
Optional Stop

Lucignano

One of the most unusual towns in Tuscany — built on a perfectly elliptical plan. Inside the Museo Civico, the Albero d'Oro — a 14th-century masterpiece of goldsmithing. A fascinating and almost entirely undiscovered stop. Add 45–60 minutes.

Your driver may suggest
  • Monte San Savino — a quiet Renaissance town and birthplace of sculptor Andrea Sansovino. A 45-minute stop, almost no tourists.
🚘 Final stretch into Cortona — ~1h 45min direct
Arrival
~1h 45min direct
Drop-off

Your Destination in Cortona

Dropped off directly at your hotel, agriturismo or private villa in Cortona, the surrounding hillside or the Val di Chiana. Door to door — to the exact address, at the exact time you need.

Flexible timing — your transfer, your pace. Want to stop in Arezzo and skip the outlets? Add Lucignano on the way? The itinerary is confirmed in advance around what you want. Extra stops are charged at €80/hr — no surprises on the day.

Extra stops — add to your transfer

🛍

The Mall Valdichiana

Gucci, Prada, Bottega Veneta — luxury brands at outlet prices.

+1–4 hours
👜

Space Outlet

Prada and Miu Miu factory outlet — one of Italy's best kept secrets.

+1–2 hours
🏬

Valdichiana Outlet Village

130+ brands in a pedestrian village — fashion, sport, lifestyle.

+1–3 hours
🏛

Arezzo

Piero della Francesca frescoes and the spectacular Piazza Grande.

+1.5–2 hours
🏰

Castiglion Fiorentino

Logge del Vasari and panoramic views over the Val di Chiana.

+45–60 min
💍

Lucignano

Elliptical medieval town and the golden Tree of Gold masterpiece.

+45–60 min
🏛

Monte San Savino

Renaissance town and birthplace of sculptor Andrea Sansovino.

+45 min
📍

Have somewhere else in mind?

If it's along the way, we stop there. A vineyard you read about, a village a friend recommended, a restaurant you've been wanting to try — just tell us when you book and we'll make it happen.

💬 Tell us your stop
Cortona hilltop town Val di Chiana private transfer Florence
Pricing

What's Included &
How to Get Your Price

The transfer price depends on your exact pickup address in Florence, your destination in Cortona, and any extra stops you'd like to add. All prices are fixed — no meters, no surprises on the day.

✓ Always included

  • Private Mercedes E-Class or Vito
  • Professional English-speaking driver
  • Door-to-door pickup & drop-off
  • All fuel, motorway tolls & parking
  • Complimentary water on board
  • Wi-Fi on board (Vito / V-Class)
  • Flight/train monitoring if needed
  • WhatsApp coordination

+ Extra stop options

  • The Mall Valdichiana (+1–4h)
  • Space Outlet — Prada (+1–2h)
  • Valdichiana Outlet Village (+1–3h)
  • Arezzo city centre (+1.5–2h)
  • Castiglion Fiorentino (+45–60min)
  • Lucignano (+45–60min)
  • Monte San Savino (+45min)
  • Shopping & personal expenses

💬 The price is fixed and confirmed before you travel. Send us your pickup address in Florence, your destination in Cortona, and any stops you'd like to add — we'll reply with a precise quote within a few hours. No obligations, no hidden fees.

Travelling in a luxury Mercedes — view our fleet →

Frequently Asked Questions

Everything You Need
to Know

Questions about the private transfer from Florence to Cortona? We've answered the most common ones below.

We pick up from any address in Florence city centre, Fiesole, the Florentine hills and surrounding areas — hotels, villas, B&Bs, agriturismi and private residences. Just send us your exact address and we'll confirm the pickup time and price.

The direct transfer from Florence city centre to Cortona takes approximately 1 hour 45 minutes. With extra stops, total journey time depends on how long you spend at each location — all confirmed in advance when you book.

Yes — the stops we suggest are simply the places we know work best along this route. But if you have somewhere else in mind — a specific vineyard, a village you've read about, a restaurant you want to try — just tell us when you book and we'll add it.

The only thing we ask is that the stop is along the way — so the detour doesn't add unnecessary kilometres or time to your journey. Think of it as staying within the natural flow of the route rather than making a major deviation. If you're not sure whether your chosen stop qualifies, just ask us — we'll tell you honestly.

Extra stops are charged at €80 per hour of waiting time, regardless of where you stop.

Absolutely — the three outlets (The Mall Valdichiana, Space and Valdichiana Outlet Village) and the medieval towns (Arezzo, Castiglion Fiorentino, Lucignano, Monte San Savino) are all in the same valley. You can combine shopping and sightseeing in the same journey. We'll plan the order and timing so everything flows smoothly.

Yes — we drop off at any address in Cortona town centre, the surrounding hillside, countryside villas and agriturismi in the area. The historic centre of Cortona has restricted traffic zones — your driver knows the access rules and will get you as close to your destination as possible.

Yes — Cortona's train station (Camucia-Cortona) is at the bottom of the hill, 3 km from the historic centre, with no direct connection. From Florence, you'd need a train to Camucia then a local bus or taxi up the hill. With luggage, this is complicated and time-consuming. A private transfer is door-to-door and takes the same time as the train journey alone.

The Mall Valdichiana is the luxury flagship — Gucci, Prada, Bottega Veneta, Valentino, Saint Laurent, Burberry and more in a stylish open-air centre. Space Outlet is the Prada and Miu Miu factory outlet — less known, extraordinary prices. Valdichiana Outlet Village is larger and more accessible with 130+ brands across fashion, sport and lifestyle. All three are within a few km of each other.

The Mercedes E-Class seats up to 3 passengers with luggage. The Mercedes Vito / V-Class seats up to 6 with ample space for suitcases and shopping bags. For larger groups we can arrange multiple vehicles.

Send us your pickup address in Florence, your destination in Cortona and any stops you'd like to add on WhatsApp or via the quote form. We'll reply with a fixed price within a few hours. No obligations, no hidden fees — the price we quote is the price you pay.

Ready to Travel to Cortona?

Send us your pickup address, destination and any stops you'd like. We'll reply with a fixed price within a few hours.