Tuscany Medieval Towns Tour with Wine Tasting
From€65
9 hours
Florence, Italy
About this activity
Discover Tuscany's medieval towns—Siena, San Gimignano, and Monteriggioni—on a guided tour from Florence, including a Chianti wine tasting and scenic countryside views.
Highlights
- Explore Siena's historic center
- Visit San Gimignano's medieval towers
- Discover Monteriggioni's ancient walls
- Enjoy a Chianti wine tasting
- Scenic drive through Tuscan countryside
Full description
Step back in time and immerse yourself in the rich history of Tuscany's medieval towns. On this full-day tour from Florence, you'll explore the UNESCO World Heritage site of Siena, renowned for its stunning cathedral and the historic Piazza del Campo. Wander through the charming streets of San Gimignano, famous for its towering medieval architecture, and visit the fortified town of Monteriggioni, which inspired Dante's 'Divine Comedy.' Along the way, enjoy a delightful wine tasting in the picturesque Chianti region, savoring the flavors of Tuscany's renowned wines. This tour offers a perfect blend of history, culture, and culinary delights, all set against the backdrop of the stunning Tuscan landscape.
Included / Excluded
- Guided tour of Siena, San Gimignano, and Monteriggioni
- Wine tasting in the Chianti region
- Transportation from Florence in an air-conditioned vehicle
- Meals and personal expenses
Itinerary
1
There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.
Duration: 45 minAdmission: NOT_APPLICABLE
2
After about 40 minutes by bus, arrive in Monteriggioni, a charming medieval fortress set atop a hill. Enjoy 45 minutes of free time to stroll through the village squares and soak up its timeless atmosphere. Guests may also choose to walk along the fortress walls (optional, extra cost).
Duration: 1 hourAdmission: NOT_APPLICABLE
3
Continue to Siena, one of Tuscany’s most beautiful historic cities. Guests who select the Classic Tour option will enjoy a 1-hour guided walking tour with a professional guide, focusing on the city’s main highlights (exterior visits only). Guests with the Semi-Independent option will have approximately 2.5 hours of free time to explore Siena at their own pace.
Duration: 3 hoursAdmission: NOT_APPLICABLE
4
During the guided tour, admire Piazza del Campo from the outside, one of Europe’s most stunning medieval squares. Your guide will explain its unique shell shape and its role as the setting of the famous Palio horse race, as well as the exterior of the Palazzo Pubblico and the Torre del Mangia.
Duration: 30 minAdmission: NOT_APPLICABLE
5
The final stop of the Siena visit is the Siena Cathedral, admired from the outside. Learn about this magnificent example of Italian Gothic architecture, renowned for its intricate marble façade.
Duration: 30 minAdmission: NO
6
After lunch, travel on to San Gimignano, the medieval town famous for its skyline of towers. Enjoy free time to wander through its cobblestone streets, browse local shops, or relax with a coffee in one of the charming squares.
Duration: 1 hourAdmission: NOT_APPLICABLE
7
During your free time, you may choose to visit the Collegiata, the town’s main church, known for its well-preserved frescoes and Romanesque architecture (entrance optional).
Duration: 15 minAdmission: NO
8
During your free time in San Gimignano, you may choose to stop at the famous Gelateria Dondoli, an award-winning gelato shop located in the main square. This is a great opportunity to taste some of Italy’s most renowned artisanal gelato (not included in the tour price).
Duration: 5 minAdmission: NO
9
End the day at a delightful wine estate in the heart of the Chianti region. Here, a wine host will guide you through a tasting of three Chianti wines, accompanied by light snacks, offering a perfect taste of the Tuscan countryside.
Duration: 1 hourAdmission: NOT_APPLICABLE
10
In the evening, relax on the journey back to Florence, bringing an unforgettable day in Tuscany to a close.
Duration: 1 hourAdmission: NOT_APPLICABLE
Meeting point
Start Location
Unknown location
Important information
Know before you book
- Tour operates rain or shine; dress appropriately for the weather.
- Wine tasting is included; bring ID if you plan to participate.
- Confirm the meeting point and time upon booking.
Know before you go
- Wear comfortable walking shoes for cobblestone streets.
- Bring a camera to capture the scenic views and historic sites.
- Check the weather forecast and dress accordingly.
Cancellation policy
Free cancellation up to 1 days before the activity starts
For a full refund, cancel at least 24 hours before the scheduled departure time.
Accessibility
- Stroller Accessible
- Easy Public Transport
- Infants Required On Laps
- Infant Seats Available
Good to know
- May be operated by a multi-lingual guide
- Please note that the given order of the visits may change
- Kindly note that the Semi independent option does not include the professional guide in Siena
- LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
- HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax
Traveler reviews
4.62,938 reviews
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Wine Tasting Trip
Cecelia was a fantastic tour guide, very helpful and well organized, with the help of Margarita and the bus driver( sorry forgot his name !) it made a perfect trip to see the beautiful villages and wine
philwG2115DLMay 25, 2026TRIPADVISOR
A worthwhile experience
It was a day well spent. The tour guide Cecilia, ably assisted by Margherita and bus driver Lucca, were all excellent in their knowledge and service.
anilw572May 24, 2026TRIPADVISOR
Fantastic day in Tuscany
It was a great day with Lorenza and Luca. We enjoyed all three towns and the wine experience. Lorenza provided us with information as needed. It was an easy way to see all 4 stops.
Compass09862469457May 24, 2026TRIPADVISOR
A Taste of Tuscany!
If you only have so much time in Tuscany, then this is the trip for you. Well organized and they communicated leading up to the excursion so you were well informed. The country side views captured what you imagine and Siena and San Gimignano were amazing experiences. Our family found San Gimignano to be exceptional and the towers and antiquity of it all was what we were looking for. The gelato at Dondoli was the best we have had and they are award winning. Celica and Marguerite kept us on time and coordinated so a shout out to them with a decent sized crew
740chadfMay 24, 2026TRIPADVISOR
Great tour!!
Great tour, highly recommend. Great pace and great staff. Cecelia, Margerita, and Luca were awesome
M370UCkurtwMay 24, 2026TRIPADVISOR
Additional information
A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements
May be operated by a multi-lingual guide
Please note that the given order of the visits may change
Please inform us of any food intolerance or allergy in advance
Kindly note that the Semi independent option does not include the professional guide in Siena
LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Saturday, Sunday - min 2 pax