Private Tuscany Day Trip: Siena, San Gimignano & Chianti4.7(26,099 Reviews)8 hours
From€105.00per person
Listing ID : 50218
4.7(26,099 Reviews)
Private Tuscany Day Trip: Siena, San Gimignano & Chianti
8hDuration
Max 12 peopleGroup Size
EnglishSpeaking Guide
Mobile ticketAccepted
About this experience
Duration8 Hours
Group SizePrivate Group
Starts AtFlorence, Italy
LanguagesEnglish
Private Day Tour from Florence
Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region
A full-day chauffeur-driven journey through the timeless landscapes and historic towns of Tuscany
This private Tuscany tour from Florence offers a curated full-day experience through three of the region's most celebrated destinations, travelling at your own pace with a dedicated chauffeur and no large crowds to navigate.
Tuscany's countryside, medieval hill towns and wine culture represent some of Italy's most enduring travel experiences. This tour brings together the best of all three in a single, well-paced day, moving from the grandeur of Siena to the intimate towers of San Gimignano and finally into the rolling vineyard landscapes of Chianti.
The private format means your group sets the tone. Whether you prefer longer stops for photography, leisurely lunches or spontaneous detours through the countryside, the itinerary adapts to your interests rather than a fixed group schedule.
An optional wine tasting at a family-run winery rounds out the day with a genuine introduction to local production methods and regional flavours, offering something beyond standard sightseeing.
Tour Highlights
Explore Siena's Piazza del Campo, Palazzo Pubblico and the Gothic Cathedral, three of Italy's most significant medieval monuments.
Walk beneath the 13 surviving towers of San Gimignano, a UNESCO World Heritage Site that defines the skyline of medieval Tuscany.
Travel through the Chianti wine region and take in iconic views of vineyards, cypress trees and olive groves across rolling hills.
Enjoy an optional wine tasting at a family-run winery with an introduction to traditional Tuscan wine-making and local produce.
Travel in comfort with a private chauffeur-driven vehicle throughout the entire day, with no shared coaches or fixed group schedules.
Stop for photographs at scenic viewpoints across the Tuscan countryside, timed around your group's preferences.
Itinerary
1
Departure from Florence
Your private vehicle departs from Florence and heads south through the Tuscan countryside toward Siena. The drive itself offers an early introduction to the region's characteristic landscape of vineyards and forested hills.
2
Siena — Medieval City and Cathedral
Arrive in Siena and spend time exploring Piazza del Campo, the fan-shaped central square famous for hosting the Palio horse race. The nearby Cathedral is one of Italy's finest examples of Gothic architecture, and Palazzo Pubblico completes the trio of essential sights in this compact, walkable city.
3
San Gimignano — The Town of Towers
Continue to San Gimignano, where 13 medieval towers rise above a well-preserved hilltop town. Beyond the towers, the town offers local wine, food artisans and an atmosphere that has changed little over centuries.
4
Chianti Wine Region
Pass through the heart of the Chianti wine region, where terraced vineyards and olive groves define the landscape. An optional stop at a family-run winery includes a guided introduction to local wine production and a tasting of regional wines and produce.
5
Return to Florence
Your chauffeur drives you back to Florence, completing a full day that covers the cultural, historical and gastronomic depth of Tuscany in a single, manageable itinerary.
What Is Included
Included
Private chauffeur-driven vehicle for the full day
Hotel pickup and drop-off in Florence
All transportation between destinations
Flexible itinerary adapted to your group
Not Included
Entrance fees to monuments and museums
Meals and beverages
Optional wine tasting at winery
Gratuities for the driver
Important Information
This is a private tour. All logistics, pace and stops are managed around your group's preferences. Confirm any optional add-ons such as wine tasting at the time of booking.
Duration
Approximately 8 hours including all travel and stops between Florence, Siena, San Gimignano and the Chianti region.
Meeting Point
Pickup is arranged from your hotel or a central location in Florence. Confirm the exact address at the time of booking.
What to Bring
Comfortable walking shoes are recommended for the cobbled streets of Siena and San Gimignano. Bring sun protection and a light layer for cooler seasons.
Cancellation
Cancellation terms are confirmed at the time of booking. Review the policy carefully before reserving your place.
Accessibility
The historic centres of Siena and San Gimignano contain steep cobbled streets and steps. Contact the operator in advance to discuss accessibility requirements.
Age Range
This tour is suitable for all ages. The difficulty level is easy, with a relaxed pace throughout the day.
Reserve Your Private Tuscany Day Tour
Secure your spot for a private, chauffeur-driven day through Siena, San Gimignano and the Chianti wine region, one of Tuscany's most rewarding full-day itineraries from Florence.
Is this tour suitable for families with children?▼
Yes, the tour is rated easy and operates at a flexible pace, making it appropriate for families. The private format allows you to adjust stops and timing to suit younger travellers.
Can we skip one of the destinations and spend more time elsewhere?▼
As a private tour, the itinerary can be adjusted based on your group's preferences. Discuss any changes with the operator at the time of booking.
Is the wine tasting included in the tour price?▼
The wine tasting at the family-run winery is an optional add-on and is not included in the base tour price. It can be arranged when booking.
Do we need to book entrance tickets to Siena's Cathedral in advance?▼
Entrance fees for monuments including the Cathedral are not included in the tour. It is advisable to book tickets in advance during peak season to avoid long queues.
Where exactly does the tour start and finish?▼
The tour starts and finishes in Florence with hotel pickup and drop-off included. The precise meeting point is confirmed after booking.
What is the best time of year to take this tour?▼
Tuscany is rewarding year-round, but spring and autumn offer the most pleasant temperatures and the most scenic countryside. Summer months are busy in all three destinations.
Private Tour TuscanyFlorence Day TripSiena TourSan GimignanoChianti Wine RegionTuscany CountrysideMedieval TuscanyWine Tasting ItalyChauffeur Tour ItalyItalian Hill TownsTuscany Itinerary
This private tour departs from Florence, the regional capital of Tuscany in central Italy, and travels south through the Chianti wine corridor before reaching Siena, a UNESCO-listed medieval city approximately 75 kilometres from Florence. The route continues northwest to San Gimignano, a hilltop town in the Province of Siena renowned for its 14th-century tower houses and designated a UNESCO World Heritage Site. The Chianti Classico zone, situated between Florence and Siena, is one of Italy's most recognised wine-producing areas and forms a key part of the geographic and cultural context of this itinerary. All three destinations sit within the Tuscan landscape of rolling hills, cypress alleys and terraced vineyards that defines the region internationally.
Type: Private Guided Day Tour | Region: Tuscany, Italy | Departing From: Florence | Destinations: Siena, San Gimignano, Chianti | Duration: 8 Hours | Difficulty: Easy | Category: Cultural, Wine and Gastronomy, Historical | Suitable For: Couples, Families, Small Groups
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