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San Gimignano, Monteriggioni, and Siena from Florence Semi-Private Day Trip


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Experience the Tuscany countryside on this small group tour with 7 people or less. Head to San Gimignano from Florence and take in the town's towers, roam the Monteriggioni Castle, and unravel the vast history of Siena, a UNESCO World Heritage site. Discover the captivating rolling hills and medieval towns of Tuscany from Florence on this semi-private tour. Board an air-conditioned Mercedes-Benz vehicle and travel to Siena from Florence. Explore its Piazza del Campo, where the Palio di Siena race is held. Maximize your free time and visit the stunning Siena Cathedral, which boasts Gothic spires and an imposing bell tower. Get recommendations from your expert guide on the best place to get lunch. Head to San Gimignano and marvel at its medieval towers. Its impressive skyline has resulted in the town being hailed as the medieval Manhattan. Bring your camera with you and take pictures of the UNESCO World Heritage site's timeless buildings. Cap off your Florence day trip at majestic Monteriggioni. Be greeted by its centuries-old walls and fortifications. Unravel its medieval history with help from your guide.

Cancellation Policy

  • Any cancellations made between 7 business days (08:00 local time) to 3 business days (08:00 local time) prior to the activity will be subject to a charge of 50% of the total amount.
  • Any cancellations made after 08:00 local time, 3 business days prior to the activity will be subject to a charge of 100% of the total amount.

Activity Detail


  • Round-trip transportation by Mercedes-Benz or similar
  • English-speaking guide/driver

Min/Max Quantity To Book

  • Max Qty: 7 (Maximum tickets can be booked)

Start Timings

  • 09:00


  • 9 (hrs)

Check In/Pickup Location Details

  • Go directly outside the Cafe Paskowski in Piazza Repubblica in Florence, where you will find your guide holding a sign with Avventure Bellissime written on it.
    Model type: A/C Mercedes vehicle or similar
    Capacity: 8 people per van


  • Children must be accompanied by an adult.
  • This activity is not fully wheelchair accessible. However, please indicate upon booking whether you need wheelchair assistance so the tour will take alternative routes.
  • If less than 2 participants are booked, the activity may not operate.

Additional Notes

  • The activity provider does not assume any responsibility for your valuables and/or personal belongings.
  • This activity operates regardless of weather.
  • To guarantee an exclusive experience, this tour operates at a maximum of 7 participants.

Dressing & Items to Bring

  • Walking shoes
  • Comfortable clothing
  • When entering religious sites, please make sure your shoulders, arms, stomachs and knees are covered out of respect for a place of worship.

Requirement(s) - other

  • Confirmation is not required. But in case you want to reconfirm your booking, you may contact the activity provider 1-2 days prior to travel date. Your voucher has the necessary contact information listed.
  • Please indicate the weight and height of the children upon booking so the tour provider can supply child seats as required by Italian law.


San Gimignano, Monteriggioni, and Siena from Florence Semi-Private Day Trip
08:50:00 Check-in Outside Cafe Paskowski in Piazza Repubblica

Day: Day1
09:00:00 Travel to Siena from Florence

Day: Day1
Head to the historic Siena, a Tuscan hill town, home of the famed Piazza del Campo. This town is where the renowned Palio horse race is held. Spend your time exploring the city and stroll through its medieval, narrow streets. Visit the Duomo di Siena which gives the Milan Duomo a run for its money.
Day: Day1
Free Time for Lunch
Ask your driver for recommendations on where to grab a bite to eat. Discover the taste of Tuscany as you indulge in a delectable lunch at a local restaurant and try Siena's specialities like cavallucci and panforte at your own expense.
Day: Day1
San Gimignano
Head to the UNESCO World Heritage site of San Gimignano and marvel at its towering buildings. Taste the flavors of Tuscany with a cup of gelato at your own expense in Piazza della Cisterna and get a chance to buy a bottle of the town's famous export—Vernaccia di San Gimignano.
Day: Day1
Stop by medieval Monteriggioni and admire its centuries-old walls and structures. Get an unobstructed view of the Chianti region and discover why the town has been featured in works like Assasin's Creed and Dante Alighieri's Divine Comedy.
Day: Day1
Return to Florence

Day: Day1
18:00:00 Drop-off at Piazza Repubblica

Day: Day1

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