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Guided Tours

From Florence: Siena & San Gimignano Day Trip with Wine Tastings & Lunch

Siena Cathedral with tourists in the square, part of San Gimignano, Siena, Monteriggioni, Chianti day trip.
Group walking through vineyard on Siena, San Gimignano, and Chianti day trip.
Visitors at the steps of a historic church in San Gimignano, Italy.
Wine being poured into a glass during a Chianti tasting on a Florence day trip.

Duration

9 hrs - 11 hrs

Open today

10:00am - 7:00pm

Free cancellation

Free cancellation up to 24 hours before the start of your experience

Book now, pay later

Book now without paying anything. Cancel for free if your plans change.

Guided tour

Transfers available

Meals included

Indulge in a sumptuous meal as a part of your experience

Explore Siena & San Gimignano in a day, wine, views, and a laid-back Tuscan lunch included.

    • Discover two of Tuscany’s most iconic hill towns in one relaxed day trip from Florence.

    • Enjoy free time in both Siena and San Gimignano to explore at your own pace.

    • Taste regional flavors with a winery visit, 3 wine tastings, and a traditional Tuscan meal.

    • Upgrade to a guided Siena tour with optional Cathedral access for a deeper cultural experience.

    • Travel comfortably with round-trip AC transport and a multilingual tour leader.

    • Round-trip AC coach transfers from Florence

    • Onboard Wi-Fi access

    • Multilingual tour leader

    • Free time in Siena & San Gimignano

    • Winery visit with 3 wine tastings

    • Traditional Tuscan lunch

    • Siena guided tour (as per option selected)

    • Siena Cathedral guided tour (as per option selected)

  • TOTAL DURATION10 hours 30 minutes
    MODE OF TRANSFERA/C Bus
    Central Florence
    Start point

    Central Florence

    Get direction
    71 min by a/c bus
    78.3 km
    Siena

    1. Siena

    2 attractions

    Highlights

    59 min by a/c bus
    45.5 km
    Chianti Classico

    2. Chianti Classico

    1 activity

    Things to do

    55 min by a/c bus
    46.4 km
    San Gimignano

    3. San Gimignano

    1 attraction

    Highlights

    70 min by a/c bus
    61.1 km
    Central Florence
    End point

    Central Florence

    Get direction

    Your ending point would be same as your start point

  • You can cancel these tickets up to 24 hours before the experience begins and get a full refund.

  • 842 reviews

    How do we collect reviews?

    These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.

    529
    132
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    112

    What our guests say

    Adrianus V

    Couple
    Verified booking
    Jul 2025
    Supervisors Martha and Julio provided perfect guidance. Clear in information and always approachable. TOP With a wine company, we expected a winery in the countryside. This was a factory site. So ambience was a bit less, despite the enthusiastic employee of the winery. Nice and enthusiastic. Despite the severe thunderstorm in Siena we had a nice day.

    Mihnea D

    Couple
    Verified booking
    Jun 2025
    Our hosts Ilaria & Martina were friendly and well prepared with useful information about the places we visited during our trip. We loved all the cities, castles and nature we saw during that day and will be happy to come again for another tour.

    Fraser N

    Family
    Verified booking
    Mar 2026

    Heila C

    Family
    Verified booking
    Jul 2025

    Bernard D

    Family
    Verified booking
    Jul 2025
  • Start your day with a comfortable departure from Florence, traveling through the rolling hills of Tuscany with onboard Wi-Fi and a multilingual tour leader.

    Siena

    Arrive in Siena, a city steeped in history and tradition. Stroll through Piazza del Campo, the heart of the city and home to the famous Palio horse race. Explore at your own pace or upgrade to a guided tour to uncover stories behind its medieval streets and landmarks. If selected, step inside the stunning Siena Cathedral to admire its intricate interiors.

    Winery in Chianti

    Head into the Tuscan countryside for a relaxing winery stop. Enjoy a traditional meal paired with three wine tastings, surrounded by vineyard views that define the region.

    San Gimignano

    Continue to this UNESCO-listed hill town known for its striking medieval towers. Wander through cobbled streets, visit local shops, and take in panoramic countryside views.

    Return to Florence in the evening after a laid-back day of culture, food, and scenic landscapes.

  • What to bring

    • Comfortable walking shoes

    • Valid photo ID

    • Clothing that covers shoulders and knees for Siena Cathedral (if visiting)

    Accessibility

    • Not wheelchair accessible

    • Not suitable for prams/strollers

    What’s not allowed

    • The wine tasting experience is restricted for guests under the age of 18 years.

    • Guests under 18 can join the tour if they are each accompanied by at least one adult.

    Additional information

    • Please note that the order of visits is subject to change.
    • Your voucher will be emailed to you shortly.

    • Display the voucher on your mobile phone with a valid photo ID at the starting point.

    • Please check your final voucher for the starting point details & specific instructions.

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