SIENA & CHIANTI PRIVATE ESCAPE

Siena’s historic center and the scenic Chianti wine region, including vineyards and medieval villages.

Explore Tuscany on a private day visiting Siena's historic sites and Chianti's vineyards, enjoying culture, architecture, and exceptional wine.


Tour Type

Private Chauffeured Tour


Duration

Full Day (9:00 AM – 6:30 PM)


Reviews

5.0 ★ ★ ★ ★ ★ 


Price

From €750 per group (1–2 people)

A Day of Elegance and Tuscan Flavor

Immerse yourself in the heart of Tuscany with a private, luxurious day discovering the historic splendour of Siena and the rolling vineyards of Chianti. This exclusive experience combines rich culture, stunning architecture, and world-class wine for an unforgettable journey.

  • What will I experience on the Siena & Chianti Tour and what makes it special?

    Our exclusive Siena & Chianti experience offers an immersive journey into the heart of Tuscany, combining rich cultural heritage with world-class wine exploration:


    In Siena, you'll discover:

    • The UNESCO-listed historic center with its well-preserved medieval architecture
    • The magnificent Siena Cathedral (Duomo di Siena) with its incredible marble work and artistic treasures
    • The famous shell-shaped Piazza del Campo, home to the legendary Palio horse race
    • Charming winding medieval alleys filled with traditional shops and authentic atmosphere
    • Optional guided exploration with a local expert who can reveal 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
    • Stunning 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 processes during a private cellar tour
    • A leisurely authentic Tuscan lunch in either a traditional trattoria or countryside estate

    Throughout the day, you'll travel in luxury with a private vehicle and dedicated driver/guide, ensuring a personalised experience that captures the true essence of Tuscany's cultural and culinary treasures.

  • What is the typical itinerary and what practical details should I know?

    While we can customise the day to your preferences, here's our sample itinerary:


    9:00 AM: Convenient pickup from your accommodation in Florence (pickups outside Florence available on request)

    10:00 AM: Arrival and drop-off 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 walk 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 selected restaurant or countryside villa in the Chianti region

    2:30 PM: Exploration of 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: Begin 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
    • Comfort: Bottled water provided on board
    • Group size: Private tour customized for your party (1-7+ people)
    • Accessibility: Please inquire about specific accessibility needs
  • What are the costs involved and what's included in the tour price?

    Our transparent pricing structure for this exclusive private experience is:

    • €750 per group for 1-2 people
    • €850 per group for 3-4 people
    • €950 per group for 5-7 people
    • Custom quotes available for larger groups upon request

    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
    • Bottled water on board
    • Booking assistance for lunch and wine tasting

    Additional costs (not included in base price):

    • Guided tour of Siena with 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 requested in advance)
    • Optional activities or enhancements
    • Gratuities (at your discretion)

    We're happy to provide exact pricing for all additional services when booking to ensure complete transparency and help you plan your budget accordingly.

  • How can I personalise this tour and what do I need to know about booking?

    We offer numerous ways to enhance and customise your Siena & Chianti experience:


    Tour enhancement options:

    • Add a hands-on cooking class in a Chianti farmhouse
    • Book a private Palio-themed walking tour with a Contrada expert for insider knowledge of Siena's famous horse race
    • Include a second wine estate visit for a comparative tasting experience of different Tuscan vintages
    • Request specific wineries or wine varieties of interest
    • Adjust timing to spend more time in either Siena or the Chianti region
    • Arrange special celebration moments for birthdays, anniversaries, or proposals
    • Customise lunch experiences from casual trattorias to gourmet estates

    Booking information:

    • Contact: Heliana Vogli at FlorenceConnection
    • Based in: Florence, Tuscany, Italy
    • Cell phone: +393397792426
    • Advance booking recommended, especially during peak season
    • Please mention any dietary restrictions, wine preferences, or special interests when booking
    • Comfortable walking shoes recommended for Siena's cobblestone streets
    • Credit cards accepted at most wineries, but having some cash (Euro) is advisable for small purchases
    • Any entry fees to monuments/museums should be requested at time of booking
    • Customised itineraries available upon request

From Our Time in Tuscany

GALLERY

What Makes Our Tours Special

From private walking tours in Florence to exclusive vineyard tastings and chauffeured countryside escapes, every Florence Connection experience blends elegance, authenticity, and a personal touch — curated to match your passions and desires.

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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Via del Proconsolo, 16 Florence, 50122

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