Day Trips

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

Name: From Florence: Pisa, Siena, San Gimignano & Chianti Day Trip with Wine Tasting & Lunch
Start: 2026-09-02T07:45:00
End: 2026-09-02T19:45:00
Location: Florence

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(1,951)

Arian D

Group

Verified booking

Today

This was a really great tour of these towns. Lunch, views and the timing were all very nice. Plus all that the tour leader, Claudia was really great.

Marita B

Solo

Verified booking

Jun 2026

A wonderful experience. Laura was our guide and Michel was our driver. Michel is a great driver, and we felt very comfortable with his driving. Laura gave us some great suggestions on what to do and where to go. We visited Pisa, Siena, the Chianti vineyards, and San Gimignano. An experience we’ll never forget.😍❤️

Barbara G

Solo

Verified booking

Jun 2026

Excellent opportunity to make a quick visit of Toscany! Siena...St. Gimignano...and a famous tower in Pizza! The best way getting to know Chianty region as well, with a wonderfull tasting one of the world most popular products of food and vine in that area! Excellent experiance!

Igor S

Solo

Verified booking

Jun 2026

Everything was very well organized. The guide was great—he spoke both English and Spanish. We had a wine tasting paired with a nice lunch. It was an excellent 12-hour tour of three cities. I don’t regret going. I highly recommend it.

Christopher M

Couple

Verified booking

Jun 2026

Enjoyed being taken to places with a really great driver. The bus guide was very good especially impressed with 3 languages skill set. The wine tasting venue was great and very entertaining. Sienna guided tour was excellent. Great guide. Would have happily sacrificed Pisa for longer at vineyard as this seemed a little rushed. It was over lunch we gelled as a group and made new friends. Wasn't so impressed with the amount of walking involved from bus to venue. It didn't help that the temperatures were 35°C. Overall an excellent tour.

Victor M

Couple

Verified booking

May 2026

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...

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
1 hr 30 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
1 hr 30 min
30 min by a/c bus
3. San Gimignano
1 hr 15 min
1 attraction
1 hr 30 min by a/c bus
4. Pisa
1 hr 15 min
1 attraction
1 hr 30 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.

1,951 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
462
59
58
133
Guests from India, Canada, United States and over 18 countries have loved this experience
What our guests say
Arvind C
Couple
Verified booking
2 weeks ago
This trip was amazing, covered most of the places I wanted to visit ! Well planned and perfect way to see wine county Tuscany, Siena n Pisa
Tatiana S
Family
Verified booking
Last week
Our guide, Barbara, was wonderful. Everything went great. Thank you for the tour.
Adriawan L
Group
Verified booking
Jul 2026
The tour guide Robert was taken care us very good and provide us all the information required. Really appreciate and thanks
Laura P
Group
Verified booking
Jul 2026
The tour is a great way to visit three cities in one day without much hassle; hopefully they'll offer it in more languages.
Laurent R
Couple
Verified booking
Jul 2026
Difficulty understanding the guide; no French translation

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.