Private Tuscany Tour – Siena, San Gimignano & Chianti Winery Experience
A fully private chauffeur-driven tour combining medieval towns, rolling vineyards and a Chianti Classico winery in one unforgettable day.
🏛 Siena & Piazza del Campo
🍷 Chianti winery & tasting
🏰 San Gimignano medieval towers
🚘 Mercedes door-to-door
📍 Pickup from your address
Private Day Tour from Tuscany
Siena, Chianti & San Gimignano
Siena, Chianti & San Gimignano
In One Perfect Day
There is a version of Tuscany that most tourists never find — the one you reach by leaving the motorway behind and taking the winding roads through the Chianti hills. Cypress trees lining the ridge. Vineyards stretching to the horizon. A medieval city rising from the valley below. This tour takes you there.
Your private Mercedes driver picks you up directly from your hotel, villa, agriturismo or B&B — anywhere in Florence, Fiesole, Montecatini, Lucca, Forte dei Marmi, Viareggio, Pisa or the surrounding area. No shared buses, no fixed meeting points in a car park. We come to your door.
The first stop is Siena — one of the best-preserved medieval cities in Italy and a UNESCO World Heritage Site. The extraordinary shell-shaped Piazza del Campo, where the famous Palio horse race has been run since the 13th century. The black-and-white striped marble of the Duomo di Siena, one of the great Gothic cathedrals of Europe. The narrow contrada streets where every neighbourhood has its own flag, its own church, its own identity. Time is yours to explore at your own pace.
Then the road takes you into the heart of the Chianti wine region — the landscape that gave the world its most famous red wine. A visit to a local winery for a guided cellar tour and tasting: Sangiovese, Vernaccia, Brunello, olive oil. You sit at a long table, a glass in hand, and understand why people come to Tuscany and never want to leave.
The afternoon belongs to San Gimignano — the medieval Manhattan of Tuscany, its 14 surviving towers visible from miles away across the valley. Walk the stone streets, taste the famous Vernaccia di San Gimignano white wine, try the locally-made gelato that has won international awards. The town is small enough to feel like a secret and beautiful enough to stay in your memory for years.
Your driver brings you back to your starting address as the sun goes low over the Tuscan hills. The duration is flexible — typically 8 hours from Florence, up to 10 hours if you are departing from further afield. The pace is yours. This is a private tour, not a group excursion.
Every pickup address is different and every itinerary is shaped around where you are staying and how much time you want to spend in each place. Tell us your address and your interests — we will design the day around you.
Siena & Piazza del Campo
UNESCO medieval city, Gothic cathedral and the most beautiful piazza in Italy — free time to explore at your pace.
Chianti Winery Visit
Guided cellar tour and wine tasting in the heart of the Chianti Classico wine region — Sangiovese, olive oil and local products.
San Gimignano Towers
The medieval Manhattan of Tuscany — 14 towers, stone streets, Vernaccia wine and award-winning gelato.
Door-to-door pickup
From any hotel, villa, B&B or agriturismo in Florence, Montecatini, Lucca, Forte dei Marmi, Viareggio, Pisa and surroundings.
Your Day — Step by Step
Tour Itinerary
Times are flexible and adapt to your pickup location and preferences. This is a private tour — the day is shaped around you.
Morning
8:00–9:30 AM
Departure
Pickup from Your Door
Your private Mercedes driver picks you up directly from your hotel, villa, B&B or agriturismo. Pickup time is agreed in advance based on your location — typically 8:00–9:30 AM from Florence and surrounding areas.
Pickup available from Florence, Fiesole, Montecatini Terme, Lucca, Forte dei Marmi, Viareggio, Pisa and any address in between.
🚘 Scenic drive through the Chianti hills
Morning
3–4 hours
First Stop
Siena
Arrive in one of Italy's greatest medieval cities. The Piazza del Campo — the world's most beautiful piazza — the Duomo with its extraordinary black-and-white marble facade, the contrada streets where centuries-old rivalries are still very much alive.
Free time to explore on foot, visit the cathedral, climb the Torre del Mangia for panoramic views, or simply sit at a café on the Campo and watch the city breathe.
Your driver may suggest
- Torre del Mangia — the 88-metre tower overlooking the Campo. Book tickets in advance; the view from the top is worth it.
- Museo dell'Opera del Duomo — Duccio's Maestà and the original sculptures from the cathedral facade. One of the great collections of medieval art in Italy.
🚘 Into the heart of Chianti Classico
Midday
1.5–2 hours
Wine Experience
Chianti Winery — Cellar Tour & Tasting
Drive into the heart of the Chianti Classico wine region — rolling hills covered in Sangiovese vines, cypress alleys, stone farmhouses. A local family winery for a guided cellar tour and tasting of Chianti Classico, Riserva and local olive oil.
Lunch at the winery is available on request — a long table, local products, the view of the vineyard. One of the great experiences of Tuscany.
Your driver may suggest
- Castello di Brolio — the ancestral home of Baron Ricasoli, who defined the Chianti Classico blend. One of the most atmospheric estates in the region.
- Badia a Passignano — a medieval abbey surrounded by Antinori vineyards. Cellar tours and tastings available in advance.
🚘 Through the Val d'Elsa
Afternoon
2–3 hours
Second Stop
San Gimignano
The medieval towers of San Gimignano appear on the horizon long before you arrive — 14 stone towers built by rival noble families in the 13th century, a skyline unlike anything else in Italy.
Walk the stone streets, taste the Vernaccia di San Gimignano DOC white wine, try the famous gelato that has won the World Gelato Championship multiple times. Free time to explore, shop for local crafts, or enjoy the view from the walls.
🚘 Return transfer to your address
Evening
Return
Back to Your Address
Drop-off at Your Door
Your driver brings you back to your exact pickup address as the sun sets over the Tuscan hills. Total duration: approximately 8 hours from Florence, up to 10 hours from Lucca, Forte dei Marmi, Viareggio or Pisa.
⏱ Flexible timing — your tour, your pace. Want to spend more time in Siena and less in San Gimignano? Add a stop in a hilltop village or a different winery? The itinerary adapts around you. Extra hours available at €80/hr — no rushing, no groups, no compromise.
Vehicles & Pricing
Tour Prices by
Tour Prices by
Pickup Location
The price depends on your pickup address. All prices are for the full private day tour — door to door, all included. The further from Florence, the longer the day and the higher the price.
💬 Not sure about your zone? Send us your exact address on WhatsApp and we'll give you a precise quote within a few hours. All prices are fixed — no surprises on the day.
| Pickup Area | Duration | Mercedes E-Class up to 3 pax |
Mercedes Vito / V-Class up to 7 pax |
|---|---|---|---|
| Zone 1 Florence, Fiesole, Florence surroundings |
~8 hours | from€580 | from€680 |
| Zone 1 Montecatini Terme, Pistoia, Prato |
~8–9 hours | from€620 | from€720 |
| Zone 2 Lucca, Pisa |
~9 hours | from€680 | from€780 |
| Zone 2 Forte dei Marmi, Viareggio, Pietrasanta |
~9–10 hours | from€750 | from€850 |
| Custom B&B, agriturismo, other addresses |
To be confirmed | Contact us with your address for a personalised quote | |
✓ Included
- Private Mercedes vehicle
- Professional English-speaking driver
- Door-to-door pickup & drop-off
- All fuel, motorway tolls & parking
- Complimentary water on board
- Flexible itinerary & timing
- WhatsApp communication all day
- Wi-Fi on board (Vito / V-Class)
+ Additional Costs
- Winery entry & wine tasting fees
- Lunch at the winery (optional)
- Museum & cathedral entrance fees
- Torre del Mangia ticket (Siena)
- Guided tours (optional)
- Gelato, shopping & personal expenses
- Gratuities (appreciated)
What Guests Say
Siena, Chianti & San Gimignano
Siena, Chianti & San Gimignano
Reviews
Real experiences from guests who spent a private day in Tuscany with our drivers.
★★★★★
The winery stop was the highlight of our entire trip to Italy. We sat outside with a glass of Chianti Classico looking over the vineyards and didn't want to leave. Our driver knew all the best spots and was incredibly patient with our pace.
★★★★★
We were picked up from our agriturismo outside Lucca — something no group tour would ever do. The driver arrived on time, was professional and friendly throughout. Siena was breathtaking and San Gimignano is like stepping back 700 years.
★★★★★
We asked to spend more time in Siena and less in San Gimignano — no problem at all. The day was entirely ours. The gelato in San Gimignano is genuinely the best I have ever eaten. This tour is worth every euro.
Ready for Your Tuscany Day?
Send us your pickup address and travel dates. We'll take care of everything else.
Frequently Asked Questions
Everything You Need
to Know
Questions about the Siena, Chianti & San Gimignano private day tour? We've answered the most common ones below.
Yes — we pick up from any address in Florence, Fiesole, Montecatini Terme, Lucca, Pisa, Forte dei Marmi, Viareggio, Pietrasanta and surrounding areas. This includes hotels, villas, B&Bs, agriturismi and private addresses. Just send us your exact address and we'll confirm the pickup time and price.
Approximately 8 hours from Florence. From Lucca, Pisa or Montecatini it is typically 8–9 hours. From Forte dei Marmi, Viareggio and the coast it can be up to 10 hours due to the longer driving distance. We confirm the exact timing when you book based on your pickup address.
Absolutely. This is a private tour — the itinerary is yours to shape. Want more time in Siena? Want to skip one stop and add a hilltop village? Prefer a different winery? Just tell us when you book and we'll plan accordingly. There are no group schedules to follow.
The transport to the winery is included in the tour price. The winery entry fee and wine tasting are paid directly at the winery on the day — typically €15–25 per person depending on the tasting selected. Lunch at the winery is available on request at an additional cost.
We work with selected family wineries in the Chianti Classico region between Siena and Florence. The specific winery is confirmed when you book — we match it to your preferences (organic, traditional, with lunch option etc.). All wineries offer English-speaking guides and genuine local products.
For the Duomo di Siena we strongly recommend booking tickets in advance, especially in high season (April–October) — they often sell out days ahead. The Torre del Mangia (Siena's tower) also benefits from advance booking. Your driver can advise and help coordinate, but tickets are purchased directly by guests.
The Mercedes E-Class comfortably seats up to 3 passengers with luggage. The Mercedes Vito / V-Class seats up to 7 passengers — ideal for families and small groups. For larger groups contact us and we can arrange multiple vehicles.
Simply send us your exact pickup address on WhatsApp or via the quote form and 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 for Your Tuscany Day?
Send us your pickup address and travel dates. We'll take care of everything else.
Follow Us
Top cities
Services
Contact
- FlorencePisa.Taxi is operated by
- Esclusive Tours
- 📌Registered office: Via Vincenzo Bellini, 33 51016 Montecatini Terme, PT
- 📩 Direct Email
- 📞 +39 320 0366 785
- 💬 Chat on WhatsApp
- 🕒24/7 Service
© 2026 Florence Pisa Taxi. All rights reserved VAT 01741200749