Private Transfer Florence to Siena & Chianti

A fully private chauffeur-driven transfer from Florence and surroundings to Siena — with optional stops at a Chianti winery, The Mall, San Gimignano or Monteriggioni.

🚘 Florence → Siena · private transfer 🍷 Optional stop: Chianti winery 🛍 Optional stop: The Mall outlet 🏰 Optional stop: San Gimignano 📍 Pickup from your address

Private Transfer — Florence to Siena & Chianti

More Than a Transfer.
A Journey Through Tuscany.

The road from Florence to Siena is one of the most beautiful drives in Italy. Once you leave the city behind and take the old Via Cassia south through the Chianti hills, the landscape changes completely — cypress avenues, stone farmhouses half-hidden in the vines, medieval towers rising from hilltops that haven't changed in five hundred years. Most people miss all of this on a train.

Your private Mercedes driver picks you up directly from your hotel, villa, B&B or agriturismo — anywhere in Florence, Fiesole, the Florentine hills or the surrounding area. No taxi ranks, no shared shuttles, no luggage dragged through a station. We come to your door, load your bags, and take you exactly where you need to go.

The transfer from Florence to Siena takes approximately 1 hour 15 minutes by the most direct route. But this road passes through some of the finest countryside in Tuscany — and a private transfer means you can stop along the way. A glass of Chianti Classico at a family winery. An hour browsing the designer boutiques at The Mall outlet. A walk through the stone streets of San Gimignano or the perfectly preserved walls of Monteriggioni. The journey becomes part of the experience.

We serve all destinations in the Siena area and the broader Chianti region — city centre hotels, historic palazzi, agriturismi in the Val d'Orcia, country villas in the Crete Senesi. If your destination has an address, we go there.

A transfer doesn't have to be just a way to get from A to B. With a private vehicle and a flexible schedule, the road between Florence and Siena can be one of the best hours of your trip — if you want it to be.

🚘
Door-to-door service
Pickup from any hotel, villa, B&B or agriturismo in Florence and surroundings — delivered to your exact destination in Siena.
~1h 15min direct
Direct transfer or longer with optional stops. The schedule is entirely yours — depart when you want, stop where you want.
Extra stops on request
Winery, The Mall, San Gimignano, Monteriggioni — add one or more stops and turn your transfer into a private Tuscan experience.
🧳
All luggage included
Mercedes E-Class for up to 3 passengers, Vito / V-Class for up to 7. Ample luggage space — no extra charges for bags.
Your Journey — Step by Step

Your Route, Your Stops

A direct transfer or a journey through the Chianti hills 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, address confirmed — departure on schedule. Pickup available from Florence city centre, Fiesole, the Florentine hills and all surrounding addresses.

🚘 Heading south through the Chianti hills
Optional
+20 min
Optional Stop

The Mall — Luxury Outlet

Europe's finest luxury outlet is right on the road to Siena — Gucci, Prada, Bottega Veneta, Valentino, Saint Laurent and more, at outlet prices. Your driver waits while you shop. Add 1–3 hours depending on how serious you are about it.

🚘 Into the heart of Chianti Classico
Optional
+1.5–2 hrs
Optional Stop

Chianti Winery — Cellar Tour & Tasting

A detour through the vine-covered hills to a selected family winery. Guided cellar tour, Sangiovese tasting, local olive oil. The kind of stop that turns a transfer into a memory.

Your driver may suggest
  • Badia a Passignano — a medieval abbey surrounded by Antinori vineyards in the heart of Chianti Classico. One of the most atmospheric stops on this road.
  • Castello di Brolio — the ancestral home of Baron Ricasoli, the man who defined the Chianti Classico blend. Cellar tours and tastings available in advance.
🚘 Continuing south toward the medieval towers
Optional
+1–2 hrs
Optional Stop

San Gimignano

Fourteen medieval towers visible from miles across the valley — the most distinctive skyline in all of Tuscany. Walk the stone streets, taste the Vernaccia white wine, try the award-winning gelato. Your driver will be waiting when you're ready to leave.

🚘 15 minutes north of Siena
Optional
+30–45 min
Optional Stop

Monteriggioni

A perfectly circular medieval walled village just 15 minutes north of Siena — one of the best-preserved fortified towns in Italy. A short stop, but one of those places that stays with you.

🚘 Final stretch into Siena
Arrival
~1h 15min direct
Drop-off

Your Destination in Siena

Dropped off directly at your hotel, palazzo, agriturismo or any address in the Siena area, Chianti, Val d'Orcia or Crete Senesi. Door to door — no station, no taxi queue at the other end.

Flexible timing — your transfer, your pace. Want to add a winery stop? Skip the outlet and go straight to San Gimignano? 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 Outlet

Gucci, Prada, Valentino and more — luxury brands at outlet prices, 20 min from Florence.

+1–3 hours
🍷

Chianti Winery

Cellar tour and Sangiovese tasting at a selected family winery in the Chianti Classico hills.

+1.5–2 hours
🏰

San Gimignano

Medieval towers, Vernaccia wine and award-winning gelato in Tuscany's most iconic hill town.

+1–2 hours
🏯

Monteriggioni

A perfectly preserved circular walled village — one of the most photographed places in Tuscany.

+30–45 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
Chianti hills Tuscany private transfer Florence to Siena
Siena Piazza del Campo private chauffeur
The Mall luxury outlet Tuscany

Pricing

What's Included &
How to Get Your Price

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

✓ 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 luxury outlet (+1–3h)
  • Chianti winery tasting (+1.5–2h)
  • San Gimignano (+1–2h)
  • Monteriggioni (+30–45min)
  • Any other stop on request
  • Winery entry fees (paid on site)
  • Shopping & personal expenses
  • Gratuities (appreciated)

💬 The price is fixed and confirmed before you travel. Send us your pickup address in Florence, your destination in Siena, 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 Siena? 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 arrival time and price.

The direct transfer from Florence city centre to Siena takes approximately 1 hour 15 minutes via the most direct route. With extra stops, total journey time depends on how long you spend at each location — we'll plan the timing with you in advance.

Yes — and this is one of the things that makes a private transfer so different from a train or a shared shuttle. You can stop at The Mall outlet, a Chianti winery, San Gimignano, Monteriggioni, or anywhere else that takes your interest.

Extra stops are charged at €80 per hour of waiting time, regardless of where you stop. All confirmed in advance — no surprises on the day.

Absolutely — 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. If you're not sure whether your chosen stop works, just ask us — we'll tell you honestly.

Yes — we serve all destinations in the broader Siena area including Siena city centre, Chianti, Val d'Orcia, Crete Senesi, Montalcino and surrounding countryside. If your destination has an address, we go there. Country villas, agriturismi and remote farmhouses are no problem.

The base price covers the direct transfer from your Florence address to your Siena destination — from €258 for the E-Class and from €308 for the Vito/V-Class. Extra stops are charged at €80 per hour of waiting time. All prices are fixed and confirmed before travel — no meters, no supplements, no surprises.

The Mercedes E-Class seats up to 3 passengers with standard luggage. The Mercedes Vito / V-Class seats up to 6 passengers with ample boot space for suitcases. No extra charge for luggage. For larger groups we can arrange multiple vehicles.

Yes — we can arrange both the outbound and return transfer, with the same driver or a different one depending on dates. Return transfers can also include different stops on the way back. Just let us know your travel dates and we'll quote both legs together.

Bookings are confirmed by email or WhatsApp with full details — pickup address, time, destination and any stops. Payment options are confirmed at booking. The day before travel your driver will contact you directly on WhatsApp to confirm all details.

Ready to Travel to Siena?

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