Tuscany Medieval Towns Tour with Wine Tasting
About this activity
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
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
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.
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).
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.
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.
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.
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.
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).
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).
In the evening, relax on the journey back to Florence, bringing an unforgettable day in Tuscany to a close.
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
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
Roberto and Leon were...
Roberto and Leon were amazing tour guides.we loved the trip. It was so organized and clear from the beginning to the end. It was just enough for all that we saw. Unbelievable landscapes and the preparation of Roberto was excellent. Mario is the best bus driver I've ever had. He's an expert at driving and carefulness.
Prosessional, organised and interesting from start to finish
This trip was exceptional in so many ways. From the outset, the professionalism and knowledge of or guide, Roberto, ensured we were well informed of the sites before our eyes as well as organisational details. As a result, we could sit back and enjoy every moment of this very full day without any ‘what about?’ questions. Lion was our guide during lunch, and again, ensured every detail was in hand. My husband and I enjoyed our day immensely due to being in such safe and knowledgeable hands throughout the day. Also, our driver Mario, was fantastic; no erratic braking etc, just smooth driving throughout. Thank you, Roberto, Lion, and Mario for giving us a day full of fantastic memories.
Beautiful and well organised tour to Siena and nearby areas
It was a day well spent visiting Siena, San Gimignano, Monteriggione and a Tuscan winery. Guide Roberto, accompanied by Lion, gave us insightful information about the places we visited while driver Marco made the journey smooth and comfortable. Highly recommended.
Tour to Tuscany towns
It was a pleasure to have Roberto as a tour guide. Well planed, well organized and the communication system that he set up with us. Went smoothly. 😃
Friendly crew and lovely experience
Lucia, Mario, Omi (sorry if I got your name wrong) and Boris were really helpful and informative. The time allocated for each stop was reasonable, and the contextual information provided between stops were interesting. Suggestions for things to see/eat before each stop was helpful too.