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 hr - 11 hr

Open today

1:30pm - 6:00pm

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
Start point
Central Florence
Get direction
71 min by a/c bus
78.3 km
1. Siena
2 attractions
Highlights
Banca Monte dei Paschi
Siena Cathedral
59 min by a/c bus
45.5 km
2. Chianti Classico
1 activity
Things to do
Vineyard tour & wine tasting
Included in price
Tuscan lunch
55 min by a/c bus
46.4 km
3. San Gimignano
1 attraction
Highlights
Torre Grossa
70 min by a/c bus
61.1 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.

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.
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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.
Robin B
Group
Verified booking
May 2025
We loved the three beautiful cities we visited, including the crown of Tuscany which wasn't on the itinerary. Paying to walk on the city walls was interesting and views were good, but we were on metal bridges, not the actual walls. There are two different access points so be sure to try both. Lunch was at a restaurant with a very small vineyard where we could walk and take photos. The tastings were all good but primarily a sales pitch. The pasta lunch was just ok. If you take the cathedral tour in Siena (recommended but additional cost) make sure you know how to get back to the meeting point!
Milagro N
Group
Verified booking
May 2025
A lot of history in each of the towns, beautiful scenery, and comfortable rides.
Fraser N
Family
Verified booking
Mar 2026

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.

Siena Cathedral

Monday	10:00am - 7:00pm	last entry 6:30pm
Tuesday	10:00am - 7:00pm	last entry 6:30pm
Wednesday	10:00am - 7:00pm	last entry 6:30pm
Thursday	10:00am - 7:00pm	last entry 6:30pm
Friday	10:00am - 7:00pm	last entry 6:30pm
Saturday	10:00am - 7:00pm	last entry 6:30pm
Sunday	1:30pm - 6:00pm	last entry 5:30pm

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.