Guided Tours

From Florence: Pisa, San Gimignano, Siena & Chianti Day Trip with Lunch & Tuscan Tastings

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 - 12 hr 45 min

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

4.4/5

(3,915)

Yeo

Mar 2026

Verified booking

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. 🍷🌿

Luis

Mar 2026

Verified booking

A Must see if you can spare a day of your florence trip. Allesia had great information and was very clear with all the meeting points and insights. Just dont buy the guided tour in Sienna, not worth the price nor the assigned guide who read most of the things we were looking, do the walk alone and the entry to the Cathedral is a Must but the entry purchased on site.

Camilo

Jan 2026

Verified booking

I loved the tour, the diversity (four locations), and Marta's valuable guidance. She explained key historical references (in English and Spanish) and made the trip flow smoothly.

Ismael

Feb 2026

Verified booking

Excellent tour. André was a very attentive guide. We loved Siena and San Gimignano, Pisa not so much. But overall, the tour was fantastic.

Jodi

Oct 2025

Verified booking

Loved our day trip and wine tasting and lunch. We went to Siena, San Gimignano, and Pisa. The tour guides were great and informative just wished our weather was better. I got soaked in Pisa.

Esperanza

Nov 2025

Verified booking

The itinerary was crafted perfectly. Our tour guide Marco was very good, accomodating and very knowledgable. We had fun filled whole day. Highly recommended.

Take a round-trip from Florence to explore Pisa, San Gimignano, and Siena, with photo ops at the Leaning Tower, a Tuscan lunch, and an optional guided cathedral tour at Siena.

Experience a spacious ride to and from Florence with dedicated multilingual assistance on board.

Begin in Pisa with a visit to the Square of Miracles, where you’ll have plenty of time to pose with the iconic Leaning Tower.

Enjoy a satisfying lunch with locally crafted pours in San Gimignano, then explore its historic 13th-century walls and stone towers.

Discover the allure of Siena’s medieval squares, with the option to enrich your experience by adding a guided tour of the city and its cathedral.

Full-day trip around Pisa, San Gimignano, and Siena

Multilingual assistance on board

Pick up from Florence

Round-trip AC coach transfer

Lunch with local blends in San Gimignano

Guided tour of Siena city center (as per option selected)

Guided tour of Siena Cathedral and city center (as per option selected)

Hotel transfers

Personal expenses

TOTAL DURATION12 hours
MODE OF TRANSFERA/C Bus
Start point
Central Florence
Get direction
77 min by a/c bus
84.5 km
1. Pisa
1 attraction
Highlights
Leaning Tower of Pisa
81 min by a/c bus
78.8 km
2. San Gimignano
1 attraction
Highlights
Duomo di San Gimignano
Things to do
Tuscan lunch
46 min by a/c bus
41.9 km
3. Siena
2 attractions
Highlights
Piazza del Campo
Siena Cathedral
78 min by a/c bus
77 km
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.

3,915 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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Guests from India, United States, Brazil and over 18 countries have loved this experience
What our guests say
Yeo
Mar 2026
Verified booking
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. 🍷🌿
Luis
Mar 2026
Verified booking
A Must see if you can spare a day of your florence trip. Allesia had great information and was very clear with all the meeting points and insights. Just dont buy the guided tour in Sienna, not worth the price nor the assigned guide who read most of the things we were looking, do the walk alone and the entry to the Cathedral is a Must but the entry purchased on site.
Ismael
Feb 2026
Verified booking
Excellent tour. André was a very attentive guide. We loved Siena and San Gimignano, Pisa not so much. But overall, the tour was fantastic.
Maria
Feb 2026
Verified booking
Very well organized, excellent guide, very careful driver. We were able to enjoy everything.
Camilo
Jan 2026
Verified booking
I loved the tour, the diversity (four locations), and Marta's valuable guidance. She explained key historical references (in English and Spanish) and made the trip flow smoothly.

A day trip from Florence to Pisa, San Gimignano, and Siena is a scenic escape into Tuscany’s charm, think iconic landmarks, rolling vineyards, and medieval towns. You’ll snap photos at the Leaning Tower, savor local pourings over lunch, and wander cobbled streets rich with history.

Pisa

Embark on your Tuscany adventure starting with the iconic city of Pisa. As you step off the coach, be greeted by the mesmerizing Field of Miracles which includes the Cathedral, the Baptistery, and the world-famous Leaning Tower. Take the chance to snap creative photos alongside this 56-meter-tall structure with a 4-degree tilt. Or, lose yourself in the charm of local streets.

San Gimignano

From Pisa, drive to San Gimignano where a traditional Tuscan Lunch with regional pairings, (if the option is selected) will be served. After your meal, freely explore the 'Manhattan of the Middle Ages' nicknamed so for its iconic tall towers, creating a skyline reminiscent of a modern city.

Siena

The final destination is Siena, accessible via a scenic drive through the captivating Chianti countryside. Siena, a breathtaking hilltop town, boasts a wealth of art, traditions, and picturesque views.

What to bring

Comfortable walking shoes are recommended, as the tour involves a fair amount of walking.

If you plan to visit Siena Cathedral, make sure your clothing covers knees and shoulders.

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

What's not allowed

Guests under 18 years old will not be served alcoholic beverages.

Accessibility

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

Additional information

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

The sequence of visits may be adjusted due to traffic or other local conditions.

Hotel transfers are not included in the tour.

Personal expenses such as souvenirs, extra snacks, or optional upgrades are not covered.

Your voucher will be emailed to you instantly.

Please display your mobile voucher along with a valid photo ID at the meeting point.

Kindly ensure that you arrive 10-15 minutes before the start time of your tour to avoid any delays.

Meeting Point

Please check your final voucher for the meeting point details and specific instructions.