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Guided Tours

From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch

Women posing playfully with the Leaning Tower of Pisa in Italy.
Pisa Cathedral and Baptistery with tourists exploring the square.
Stone buildings in a sunny Tuscan village square, part of the Highlights of Tuscany tour.
People dining at a long table during Pisa, Siena, and San Gimignano day trip.

Duration

12 hr

Free cancellation

Free cancellation up to 48 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

A Tuscany day trip that actually earns its length; four stops, a winery lunch, and three wine tastings, all without renting a car or planning a thing.

    • Explore four of Tuscany’s most iconic destinations in one well-planned day trip from Florence.

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

    • Savor authentic Tuscan flavors with a winery visit, wine tastings, and a traditional local meal.

    • Upgrade your experience with guided tours of Siena and its cathedral or access to Pisa’s famous tower.

    • Travel comfortably with round-trip AC coach transfers and a multilingual tour leader throughout.

    • Round-trip AC coach transfers from Florence

    • Onboard Wi-Fi access

    • Multilingual tour leader

    • Free time in Pisa, Siena & San Gimignano

    • Chianti winery visit with 3 wine tastings

    • Traditional Tuscan lunch

    • Siena guided tour (as per option selected)

    • Siena Cathedral guided tour (as per option selected)

    • Leaning Tower of Pisa access (as per option selected)

    • Hotel transfers

    • Personal expenses

  • TOTAL DURATION12 hours
    MODE OF TRANSFERA/C Bus
    Central Florence
    Start point

    Central Florence

    Get direction
    77 min by a/c bus
    84.5 km
    Pisa

    1. Pisa

    1 attraction

    Highlights

    81 min by a/c bus
    78.8 km
    San Gimignano

    2. San Gimignano

    1 attraction

    Highlights

    Things to do

    46 min by a/c bus
    41.9 km
    Siena

    3. Siena

    2 attractions

    Highlights

    78 min by a/c bus
    77 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 48 hours before the experience begins and get a full refund.

  • 1,917 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.

    1.2K
    458
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    133
    India
    Armenia
    Brazil
    Singapore
    United States
    Australia
    India
    Armenia
    Brazil
    Singapore
    United States
    Australia
    Guests from India, Armenia, Brazil and over 6 countries have loved this experience

    What our guests say

    Yeo C

    Group
    Verified booking
    Mar 2026
    Had a wonderful day exploring Tuscany with a well-planned route through Pisa, San Gimignano, and Siena. Seeing the Leaning Tower of Pisa was a great start, and the medieval charm of San Gimignano and Siena was unforgettable. The wine tasting in the beautiful Chianti countryside was a highlight. Our guide was clear, friendly, and made the whole trip enjoyable. 🍷🌿

    Shailesh A

    Family
    Verified booking
    May 2025
    This was truly a quintessential journey through the Tuscany region of Italy. The itinerary was thoughtfully paced—despite being a long day trip, it included just the right amount of travel time to relax and even catch a nap. Our stop in Pisa offered just enough time to snap some great photos and pick up a few souvenirs. The highlight, however, was San Gimignano, where we indulged in exceptional wine and food tastings. The table setting was flawless, and our host did a fantastic job explaining each course. I highly recommend opting for the food tasting experience—it was delightful, even for vegetarians like us, and we enjoyed a hearty, satisfying lunch. Although our time in Siena felt a bit short (as is often the case with day trips), we thoroughly enjoyed everything we saw and experienced. If I had the chance to do it all over again, I’d choose this day trip without hesitation—for the variety it offers and the comfort with which it’s delivered.

    Tsovinar H

    Solo
    Verified booking
    Last week

    Salini B

    Family
    Verified booking
    Apr 2026

    Juliana F

    Couple
    Verified booking
    Mar 2026
  • Start your day with a comfortable departure from Florence aboard an AC coach equipped with Wi-Fi, setting the tone for a relaxed journey through Tuscany.

    Pisa

    Arrive at Piazza dei Miracoli, home to some of Italy’s most striking architecture. Take time to admire the Cathedral, Baptistery, and Monumental Cemetery, and snap photos of the iconic Leaning Tower. If you’ve chosen the upgrade, climb to the top for sweeping city views.

    Chianti

    Leave the city behind and head into the rolling hills of Chianti. Visit a local winery where you’ll enjoy a traditional Tuscan lunch paired with three regional wine tastings, surrounded by vineyard landscapes.

    San Gimignano

    Continue to this medieval hill town known for its skyline of stone towers. Stroll through its narrow streets, explore artisan boutiques, and take a break at a local café or gelateria in the main square.

    Siena

    End your day in Siena, a city rich in history and tradition. Visit Piazza del Campo, the heart of the city and home to the famous Palio horse race. With upgraded options, join a guided walking tour and explore the Siena Cathedral’s intricate interiors. Enjoy free time to relax or explore before heading back.

    Return to Florence in the evening after a full day of exploration, culture, and Tuscan flavors.

  • What to bring

    • Wear comfortable walking shoes because the tour involves a fair amount of walking.

    • If you plan to visit Siena Cathedral, wear clothing that covers your knees and shoulders.

    • Bring a valid ID if you intend to participate in the wine tasting sessions.

    Accessibility

    • The tour is not suitable for wheelchair users or guests with prams or strollers.

    What’s not allowed

    • Guests under 18 years old will not be served alcoholic beverages during the wine tastings.

    Additional information

    • Guests under 18 years old may join the tour only when accompanied by at least one adult.

    • The sequence of visits to Pisa, San Gimignano, Siena, and Chianti may change due to traffic or local conditions.

    • Hotel transfers are not included in this experience; you must reach the meeting point in central Florence on your own.

  • 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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