Siena and San Gimignano wine tour

A private Tuscany tour with gourmet experience

ask availability

Tour Details

Pick-up & drop off
Pick-up & drop off: Florence
Available
Available: All year round
A full-day immersive experience
A full-day immersive experience: 10 hours
Classification
Classification: Easy

Indulge in the ultimate sensory private Tuscany tour through the heart of Italy. Our Siena and San Gimignano wine tour is designed for those who want to combine the architectural wonders of Tuscany with its world-renowned culinary excellence. Enjoy a day of luxury, breathtaking landscapes, and premium tastings with your own private chauffeur.

Stress-Free Departure from Florence

Your day begins with a luxury pickup directly at your hotel or apartment in Florence. Relax in our premium vehicle as we leave the city behind and head into the golden hills of the Sienese countryside.

The Medieval Grandeur of Siena

Estimated Travel Time: 75 minutes

First, we reach Siena, a UNESCO World Heritage site and a masterpiece of Gothic design. Known for its “burnt sienna” brickwork and the historic Palio horse race (July 2nd and August 16th), Siena offers an atmosphere unlike any other city in Italy.

  • Piazza del Campo: Explore the world-famous shell-shaped square where history comes to life.
  • The Duomo: Marvel at the intricate marble floors and the stunning facade of one of Italy’s most beautiful cathedrals.
  • Local Delicacies: Your driver will guide you toward the best artisanal shops to taste Panforte and Ricciarelli—traditional sweets that have been made here since the Middle Ages.

Private Chauffeur Benefit: We handle the ZTL (restricted traffic zones), dropping you off in the heart of the city to maximize your sightseeing time.

Part 2: Gourmet Lunch & Chianti Wine Tasting

Estimated Travel Time: 50 minutes

The highlight of your Siena and San Gimignano wine tour takes place in the rolling hills of the Chianti region. We will escort you to an exclusive boutique winery or a traditional Tuscan estate for a true farm-to-table experience.

  • The Cellar Tour: Learn the secrets of Tuscan winemaking with a guided tour of the estate’s private cellars.
  • Gourmet Wine Pairing: Enjoy a multi-course traditional lunch featuring seasonal specialties like Cinta Senese cured meats, Pappa al Pomodoro, and handmade pasta.
  • The Tasting: Each course is perfectly paired with the estate’s finest labels, from robust Chianti Classico to elegant Riservas and local Vino Nobile.

Part 3: San Gimignano – The City of Beautiful Towers

Estimated Travel Time: 40 minutes

After lunch, we visit San Gimignano, the “Medieval Manhattan.” Famous for its 14 remaining stone towers, this town offers spectacular views over vineyards and olive groves.

  • Vernaccia di San Gimignano: Discover Italy’s first DOCG white wine—crisp, elegant, and perfect for an afternoon sip.
  • Piazza della Cisterna: Stroll through this lively medieval square and perhaps enjoy a gelato from a world-champion master.
  • Artisan Shopping: Discover local saffron and handcrafted leather goods in the charming boutiques lining the cobblestone streets.

As the sun begins to set over the hills, your driver will be waiting to take you on a scenic drive back to Florence.

Tour Details & Logistics

  • Duration: 10 Hours (A full-day immersive experience).
  • Availability: All year round.
  • Classification: Easy / Relaxed.

Included

  • Luxury private vehicle for the entire itinerary.
  • Professional English-speaking driver.
  • All vehicle costs (Fuel, tolls, parking fees, insurance and taxes).
  • Pickup and drop-off at your accommodation.

Not included

  • Museum entrance tickets.
  • Professional walking guide
  • Winery lunch and tasting fees (to be paid on-site).

ask availability Siena and San Gimignano wine tour










    See also

    Siena & San Gimignano

    Discover more

    Lucca and Pisa

    Discover more

    Shopping tour outlets

    Discover more

    Siena and Chianti

    Discover more

    San Gimignano and Chianti

    Discover more

    San Gimignano and Volterra

    Discover more

    Montalcino, Pienza, Montepulciano

    Discover more

    Montepulciano, Pienza and Orcia Valley

    Discover more

    Pisa San Gimignano and Siena

    Discover more

    Cinque Terre

    Discover more

    Assisi and Perugia

    Discover more

    Arezzo and Cortona

    Discover more

    Arezzo and Siena

    Discover more

    Customize your tour

    Discover more