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

11 hrs 30 mins - 12 hrs

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.

4.3/5(1,929)

Victor M

Couple

Verified booking

3 weeks ago

Everything was great—the guide did a wonderful job explaining each place. The vineyard is a beautiful spot, and the staff were so friendly. And finally, Pisa, with its 200-plus steps... Everything was fantastic... Kudos to our guide Marina...

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. 🍷🌿

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
Start point
Central Florence
Get direction
90 min by a/c bus
1. Siena
2 hr
2 attractions
You can choose to either freely explore Siena, or avail a guided tour of the city center and maybe even its cathedral.
Highlights
Piazza del Campo
Siena Cathedral
45 min by a/c bus
2. Chianti Vineyard
90 min
30 min by a/c bus
3. San Gimignano
75 min
1 attraction
90 min by a/c bus
4. Pisa
75 min
1 attraction
90 min by a/c bus
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.

1,929 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
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Guests from India, United States, Brazil and over 11 countries have loved this experience
What our guests say
Adrian R
Couple
Verified booking
Last week
Everything was great, and they were right on time. We loved the lunch.
Victor M
Couple
Verified booking
3 weeks ago
Everything was great—the guide did a wonderful job explaining each place. The vineyard is a beautiful spot, and the staff were so friendly. And finally, Pisa, with its 200-plus steps... Everything was fantastic... Kudos to our guide Marina...
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. 🍷🌿
See T
Group
Verified booking
3 days ago
Vanshri M
Family
Verified booking
3 days ago

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.