Guided Tours

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

Name: From Florence: Small Group Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch
Start: 2026-05-22T08:45:00
End: 2026-05-22T20:15:00
Location: Florence

Streets of San Gimignano with historic stone buildings and tourists exploring.

Vineyards and olive groves in Chianti region, Tuscany, Italy.

Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.

Wine barrels in a cellar during Chianti wine tasting tour from Florence.

Duration

10 hr 30 min - 11 hr 30 min

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 Pisa, Siena, San Gimignano, and Chianti in one day with a small group capped at 25 guests.

Enjoy a more relaxed experience with fewer crowds, smoother pacing, and better interaction with your tour leader.

Savor a traditional Tuscan lunch at a family-run winery, paired with 3 regional wine tastings.

Get free time in Pisa and San Gimignano to explore landmarks, viewpoints, and local shops at your own pace.

Travel comfortably from Florence with round-trip AC coach transfers and onboard Wi-Fi.

Upgrade to join an expert-led walking tour of Siena and uncover its medieval streets, Piazza del Campo, and rich local history.

Round-trip AC coach transfers from Florence

Onboard Wi-Fi access

English-speaking tour leader

Free time in Pisa, Siena & San Gimignano

Chianti winery visit with 3 wine tastings

Traditional Tuscan lunch

Small group of max 25 guests

Siena guided tour (as per option selected)

Entrance to Siena Cathedral

TOTAL DURATION10 hours 30 minutes
MODE OF TRANSFERA/C Bus
Start point
Central Florence
Get direction
71 min by a/c bus
78.3 km
1. Siena
1 attraction
Highlights
Palazzo Pubblico
46 min by a/c bus
41.7 km
2. San Gimignano
1 attraction
Highlights
Piazza della Cisterna
57 min by a/c bus
45.9 km
3. Chianti Classico
1 activity
Things to do
Vineyard tour & wine tasting
Included in price
50 min by a/c bus
29.1 km
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.

14 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.
8
4
2
0
0
What our guests say
Richard V
Couple
Verified booking
Aug 2025
Great experience. Our guide Lori was very friendly. The small group was great, we had a lot of fun. The organized tour was great. The only downside was that there was no French translation.
Luc B
Couple
Verified booking
Aug 2025
Sanjay B
Couple
Verified booking
Jul 2025
Jean C
Solo
Verified booking
May 2025
Professional beautiful cities interesting
Fernando S
Group
Verified booking
Nov 2024
I should have spent more time in SAN Gimignano

What to bring

Comfortable walking shoes

Valid photo ID

What’s not allowed

Large bags may be restricted at sites

Accessibility

Not suitable for wheelchair users or guests with limited mobility

Additional information

Order of stops may vary

Inform in advance of food allergies or dietary requirements

Free cancellation is available up to 48 hours before the service starts.

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.