Italy · City Tours

PRIVATE Full-Day GUIDED Tour: Siena, San Gimignano and Chianti

9 Hours Round trip from Pickup service provided in Florence. Easy pace

The journey

Trip highlights
  • 01 Private full-day tour from Florence through Siena, Chianti, and San Gimignano
  • 02 Guided visit of Siena with a licensed tour guide
  • 03 See Piazza del Campo and Siena Cathedral
  • 04 Scenic drive along the Chiantigiana Road through Chianti
  • 05 Optional lunch at a local organic farm or winery
  • 06 Stop in the medieval walled village of Monteriggioni
  • 07 Free time to explore San Gimignano at your own pace
  • 08 Private air-conditioned minivan with hotel pick-up and drop-off

Discover some of Tuscany’s most iconic hill towns on a private full-day journey from Florence. Explore Siena with a licensed guide, admire its medieval streets, Piazza del Campo, and the remarkable Siena Cathedral, then continue through the scenic Chianti countryside.

Depending on your preferred program, stop in Monteriggioni or choose an optional lunch at a local organic winery. Later, enjoy free time in San Gimignano, famous for its skyline of medieval towers, historic squares, and timeless atmosphere.

Upon arrival, admire the iconic Conch-shaped Piazza del Campo and the magnificent Siena Cathedral, true gems of Tuscan heritage.

From the itinerary

At a glance

What this trip includes

Duration 9 Hours
Tour type Private
Activity level Easy
Accommodation Included
Transport Included
Wheelchair access No
Cities Florence, Siena, Chianti, San Gimignano
Languages English, Italian

Day by day

The itinerary

1
Day 01

Discover the medieval beauty of Siena

Followed by an authorized guide, who will be at your disposal for the entire time you spend in Siena, you will explore the stunning city. Renowned throughout Italy for its medieval architecture, Siena is a feast for the eyes at every corner.

Upon arrival, admire the iconic Conch-shaped Piazza del Campo and the magnificent Siena Cathedral, true gems of Tuscan heritage. Stroll along the historic streets, where charming local shops invite you to taste authentic Tuscan food or pick up unique souvenirs 🌿✨

Visit the stunning Siena Cathedral (DUOMO)

Here too, you will be accompanied by an authorized guide, who will meet you on site to explore the Cathedral of Santa Maria Assunta, the main Catholic place of worship in Tuscany and the bishopric of Siena. Located in the square of the same name, in the heart of the city, this Italian Gothic masterpiece is one of the most remarkable and awe-inspiring churches in Italy. 🌿✨

Discover the iconic Piazza del Campo

Step into Piazza del Campo, the heart of Siena and one of the most beautiful squares in the world. Famous for its unique shell-like shape, the square is a masterpiece of medieval architecture and a gathering place full of life and history. Twice a year, it becomes the stage for the famous Palio di Siena, an unforgettable horse race that fills the city with color, tradition, and excitement. 🌿✨

Optional Full Lunch at a local organic winery

Enjoy an unforgettable lunch experience at a charming organic farm or small family-owned winery. While the owner shows you around the property, his family will prepare a delicious homemade lunch featuring fresh pasta, crostini, local meats and cold cuts, legumes, seasonal vegetables, honey, and cheeses.

Taste the farm’s own organic wines, including small-production craft wines, perfectly paired with each course. Sit back and savor your meal while enjoying a breathtaking Tuscan panorama 🌿🍷

⚠️ This optional experience may slightly reduce time in Siena and San Gimignano and will replace the visit to Monteriggioni Fortress.
If the winery lunch is not requested at the time of booking, the tour will follow the original program, including the stop at Monteriggioni Fortress.

Explore the charming village of Monteriggioni

Make a delightful stop in the small medieval fortified village of Monteriggioni, still surrounded by its original walls. Just a short drive from Siena, Monteriggioni is the perfect place for a leisurely stroll, soaking in the historic atmosphere after lunch at one of the local restaurants 🌿🏰

Discover the magic of chiantigiana road

Discover the magic of the Chiantigiana Road (SS222), one of Italy’s most beautiful routes 🇮🇹, winding through the heart of Chianti from Siena to Castellina in Chianti. Every turn offers breathtaking views, with green rolling hills, endless vineyards, and charming medieval villages 🏰.

A journey along the Chiantigiana is more than a drive—it’s an experience for all your senses: the scent of wine, the colors of the hills, and the charm of ancient villages… an adventure that will stay in your heart ❤️.

San Gimignano, the medieval Manhattan

Here we are in the stunning stronghold of San Gimignano 🏰, a true jewel of medieval Italy, known as Medieval Manhattan for its multiple towers 🏙️. Walking through its streets is like stepping back in time to the 1300s, where every corner tells a story and every stone whispers history.

Famous for its tower houses, San Gimignano rises proudly over the surrounding Tuscan hills, offering breathtaking views 🌄 that will stay in your memory forever. Take your time to wander the narrow streets, admire the medieval architecture, and capture the perfect photos 📸.

Please note: there will be no authorized guide during this stop—this is a self-guided experience, so you can explore at your own pace and fully immerse yourself in the town’s magical atmosphere ❤️.

This is our last stop of the day before returning to Florence, so savor every moment—the charm, the history, and the feeling of a town that seems frozen in time.

Cistern Square in San Gimignano

Cathedral of San Gimignano

The route

Where you'll travel

Tour route map
Round trip from Pickup service provided in Florence. 4 cities · 9 Hours

The fine print

Trip details

What's Included

  • Pick-up and drop-off at your selected hotel or location in Florence downtown
  • Licensed tour guide in Siena for 2–3 hours
  • Private minivan with air-conditioning for maximum comfort 🚐
  • English-speaking licensed driver
  • Unlimited cold mineral water 💧
  • WiFi on board 📶
  • Panoramic photo stop to capture the breathtaking views 📸

What's Not Included

  • A full lunch at the winery is available at an additional cost of €60–€70 per person to be paid on site.
  • A restaurant lunch in Monteriggioni, as per the standard itinerary, is available at an additional cost depending on what you order.

Know before you go

  • STROLLER OR PRAM ACCESSIBLE
  • INFANT SEATS AVAILABLE
  • Not wheelchair accessible ❌
  • Not suitable for pets 🐾
  • Infants must not sit on laps
  • In case of rain, umbrellas will be provided ☔ by your driver
  • Please share your mobile number at booking for easy communication during pick-up
  • Private tour for a maximum of 6 travelers (your party only)
  • Authorized guide not included
  • Minors under 18 are not allowed to consume alcohol (wine tasting)

Optional Full Lunch in the organic winery 🍷

  • Upon request at the time of booking, we can arrange a highly recommended Full Lunch in the organic winery, especially for wine lovers
  • Special menus available for celiac guests, allergies, and vegetarians
  • Choosing the Full Lunch in the organic winery excludes the visit to the Monteriggioni Fortress
  • Extra cost for full lunch in winery: approximately €60–€70 per person, payable separately

Departure & Pick-up

  • Suggested departure time: 9:00 AM
  • Pick-up time can be selected during the reservation
  • Pick-up is available only from hotels or private addresses in Florence city center
  • Train stations and airports are not included as pick-up points
  • Pick-up time may be changed up to 24 hours in advance, upon request

Additional Information

  • Our experienced drivers, deeply knowledgeable about Tuscany, will share local insights, curiosities, and hidden gems throughout the journey

Reconfirmation

⚠️ Kindly reconfirm the tour the day before.

Logistics

Meeting & route

Meeting point
Pickup service provided in Florence.
Tour start
Pickup service provided in Florence.
Tour ends at the same location as the start point.
End of the journey

Your 9 hours finish where they began, in Pickup service provided in Florence..

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