SIENA & CHIANTI PRIVATE ESCAPE
Siena’s historic center and the scenic Chianti wine region, including vineyards and medieval villages.
Discover the heart of Tuscany on a private journey through Siena’s timeless streets and Chianti’s
rolling vineyards, where history, art, architecture and world class wine blend into an unforgettable experience.
Tour Type
Cultural, Historical & Wine Private Chauffeured Tour
Duration
Full Day (9:00 AM – 6:30 PM)
Reviews
5/5 Google & Tripadvisor
Price
From €700 per group (1–2 people)
A Day of Culture and Tuscan Flavor
Immerse yourself in the heart of Tuscany on a private, luxurious day experience, discovering
Siena’s historic splendor and the rolling vineyards of Chianti. This exclusive journey blends rich
culture, breathtaking architecture and world class wine for an unforgettable day.
Tour Highlights:
Our exclusive Soul of Siena & Chianti full day private experience offers an immersive day journey into the heart of Tuscany, blending rich cultural heritage with world class wine and culinary delights:
In Siena, you'll discover:
- The UNESCO listed historic center with its remarkably preserved medieval architecture. • The magnificent Siena Cathedral (Duomo di Siena), showcasing intricate marble work and artistic treasures.
- The famous shell shaped Piazza del Campo, renowned for the legendary Palio horse race.
- Charming winding medieval alleys, brimming with traditional shops and authentic Tuscan atmosphere.
- Optional: A guided exploration with a local expert who reveals the city’s fascinating history and hidden gems (available on request).
In the Chianti Region, you'll enjoy:
- A scenic drive through one of Italy’s most celebrated wine regions.
- Breathtaking landscapes of rolling vineyards, cypress lined roads and historic estates.
- Photo stops at iconic viewpoints, capturing the essence of the Tuscan countryside.
- Private wine tasting at a renowned Chianti estate, featuring premium Chianti DOCG and Super Tuscan wines.
- Insight into traditional winemaking during a private cellar tour.
- A leisurely authentic Tuscan lunch in a traditional trattoria or countryside estate.
Throughout the day, travel in luxury with a private vehicle and dedicated driver/guide, ensuring a personalized experience that captures the true essence of Tuscany’s cultural, culinary and vinicultural treasures.
Tour Itinerary:
While we can customize the day to your preferences, here’s a sample itinerary:
- 9:00 AM: Convenient pickup from your accommodation in Florence (pickups outside Florence available on request)
- 10:00 AM: Arrival in Siena, where you'll enjoy:
- Visit to the stunning Siena Cathedral (Duomo di Siena)
- Exploration of the famous Piazza del Campo
- Leisure time to stroll through the medieval alleys and discover local shops
- Optional: Entry to the Cathedral’s interior (tickets can be arranged)
- 1:00 PM: Lunch at a carefully selected restaurant or countryside villa in the Chianti region
- 2:30 PM: Explore the Chianti wine region, including:
- Scenic drive through picturesque landscapes
- Visit to a top winery for a private cellar tour and guided tasting
- 5:30 PM: Return journey
- 6:30 PM: Drop off at your accommodation
Practical details:
- Tour duration: Approximately 9–10 hours
- Transportation: Private luxury vehicle with professional driver/guide
- Walking level: Moderate walking on cobblestone streets and some hills in Siena
- Weather considerations: Tour operates year round with seasonal adjustments
- Group size: Private tour customized for your party (1–7 people)
- Accessibility: Please inquire about specific accessibility needs
Tour Enhancements:
We offer numerous ways to enhance and customize this tour:
- Add a hands on cooking class in a traditional Chianti farmhouse.
- Book a private Palio themed walking tour with a Contrada expert, gaining insider knowledge of Siena’s iconic horse race.
- Include a second wine estate visit for a comparative tasting of distinct Tuscan vintages.
- Request specific wineries or wine varieties to tailor the experience to your personal preferences.
- Adjust the itinerary timing to spend more time in either Siena or the Chianti region.
- Arrange special celebration moments for birthdays, anniversaries or proposals.
- Customize lunch experiences, from casual trattorias to gourmet countryside estates.
Tour Price Breakdown:
Our transparent pricing for this exclusive private experience:
- €700 per group for 1–2 people
- €800 per group for 3–4 people
- €900 per group for 5–7 people
- Custom quotes available for larger groups upon request • VAT tax of 10% applies in addition to the above rates
What’s included in the base price:
- Private luxury vehicle with professional driver/guide for the entire day
- Flexible pickup and drop off service
- All transportation between destinations
- Assistance with bookings for lunch and wine tasting
Additional costs (not included in base price):
- Guided tour of Siena with a professional local guide: €190 additional
- Wine tasting and estate visit fees: To be paid locally at the winery
- Lunch costs: To be paid directly at the restaurant
- Entry fees to monuments/museums (can be arranged in advance)
- Optional activities or enhancements
- Gratuities (at your discretion)
We are happy to provide exact pricing for all additional services at the time of booking, ensuring complete transparency and helping you plan your day and budget with ease.
Snapshots from The Soul of Siena & Chianti Tours
GALLERY
What Makes Our Tours Special
With insider insights, luxury transportation and carefully curated stops, this tour is designed entirely for you. Let Florence Connection create an unforgettable day exploring Tuscany’s most cherished towns and regions.
Testimonials
TAGLINE
Charity Karimi
2 weeks ago

Very professional and knowledgeable. We enjoyed every bit of our tour.
Dan O'Connell
A year ago

Wonderful experience. Tour was tailored to my family’s needs with special attention to my older parents. Would highly recommend!
Luca Marilli
2 weeks ago

Professional team for the organisation, high quality wine tasting in an exclusive location. Relaxing stay and Tuscan emotions. Wonderful pool! Thank you.
Andre'a Lucca
2 weeks ago

Helena and The Florence Connection are truly the BEST guide, planner, and tour organizers I have ever experienced!
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+39 339 779 2426
Our office
Via del Proconsolo, 16 Florence, 50122

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