1 day

Italy Day Tour: Siena + San Gimignano + Monteriggioni + Chianti + Wine Tasting Included (Departing from Florence · English-Speaking Group with Optional Chinese Audio Guide)
From 25/10/2026
Group Tours
Florence - Chianti - Siena - San Gimignano - Florence
Upcoming departure dates: 2026-10-25, 2026-10-26, 2026-10-27, 2026-10-28, 2026-10-29, 2026-10-30, 2026-10-31, 2026-11-01, 2026-11-02, 2026-11-03
Day 1
Florence - Chianti - Siena - San Gimignano - Florence
Download full itinerary PDFTour departure point
D1 Florence Meeting time: 08:45 Meeting point: Ticket kiosk at Montelungo Bus Terminal, about a 5–10-minute walk from Santa Maria Novella train station. Look for staff wearing magenta jackets (Google Maps: https://maps.google.com/[email protected],11.2466917)
Itinerary details
Depart from Florence in the morning and travel to the picturesque Chianti region. Cross rolling green vineyards and hills before arriving at Monteriggioni, a medieval town nestled in the Tuscan hills. Its well-preserved city walls and peaceful, charming piazza will make you feel as though you have traveled back to the Middle Ages. Enjoy free time to stroll around and experience the unique atmosphere of this thousand-year-old town. Next, visit the medieval city of Siena. It is home to Piazza del Campo, famous for its historic Palio horse race and a fine example of Gothic civic architecture. The Palazzo Pubblico and its towering Torre del Mangia are especially striking. Guests joining the guided tour will continue to the magnificent Siena Cathedral, one of Italy’s finest examples of Gothic architecture. After the tour, enjoy free time to explore Siena’s historic center and soak up the atmosphere of this ancient city. Then head to the picturesque Chianti wine region. At a local winery, taste world-renowned Chianti wines paired with delicious homemade snacks, and enjoy a selection of wine and olive oil tastings to experience authentic Tuscan food culture. Finally, arrive at the last stop of the tour: San Gimignano. This medieval hilltop town, a UNESCO World Heritage Site, is known for its fine Vernaccia white wine and well-preserved medieval towers, earning it the nickname “Manhattan of the Middle Ages.” Wander through its ancient cobbled lanes, admire the magnificent Tuscan countryside, and experience the town’s unique charm. This tour takes you on an in-depth exploration of Tuscany’s most iconic medieval towns, the Chianti wine region, and its idyllic countryside, creating unforgettable travel memories. Tour duration: approximately 10 hours 30 minutes
Important notes
Important notes Please note that the order of visits may change depending on actual conditions. Comfortable walking shoes are recommended. This tour is not suitable for wheelchair users or guests with limited mobility. Please inform us in advance of any food allergies or special dietary requirements. Low season (November 1 to March 31 of the following year) Tours in English and Spanish are guaranteed to operate. Tours in French, Italian, or Portuguese require at least 4 guests to operate. High season (April 1 to October 31) Tours in English and Spanish are guaranteed to operate. Tours in other languages operate as follows: French: Tuesdays and Fridays (minimum 2 guests) Portuguese: Wednesdays (minimum 2 guests) Italian: Saturdays and Sundays (minimum 2 guests) Chinese-language service information If you select Chinese, attraction information and tour commentary are provided through an audio guide on a mobile app in the selected language. There is no on-site guide in that language. Throughout the tour, a professional English-speaking tour leader will accompany the group, coordinating the tour, providing emergency assistance, and sharing itinerary details such as meeting times and locations in English. Please note that Chinese-language service is available for audio tours only. If you select an additional service (such as a guided tour of Siena), it will be provided by an English-speaking local guide. However, you can still use the app to access Chinese-language introductions to Siena’s attractions. The winery tasting will also be conducted in English. Note: All times shown on this webpage are for reference only. Actual arrival times may be delayed due to circumstances beyond our control, such as weather, traffic congestion, traffic accidents, festivals or sporting events, civil unrest, or strikes. We appreciate your understanding. If you have onward travel plans involving other transportation to another city, we strongly recommend allowing at least 3 hours of extra time to avoid inconvenience caused by delays. Our company accepts no responsibility for losses arising from travel arrangements you make yourself without allowing sufficient extra time. Thank you for your understanding.
Meals
Breakfast: at your own expense Lunch: at your own expense Dinner: at your own expense
Accommodation
None
Attraction details
Pricing Information
Collapse
Included
Round-trip transportation by luxury air-conditioned coach
Professional multilingual tour leader accompanying the group
Chinese-language audio guide on the app
Professional guided tour of Siena
Free time in Siena, San Gimignano, and Monteriggioni
Visit a winery typical of the Chianti region and enjoy a wine tasting
Taste local wines, extra virgin olive oil, and specialty products
Not included
Other items not mentioned under “What’s Included”
Booking information
Collapse
Changes and cancellation policy
Free cancellation up to 72 hours before departure.
Book directly
Choose your date, departure point and room type, then review the total before booking.


![[One-Country Deep Dive] A Song of Ice and Fire: 6-Day, 5-Night Iceland In-Depth Tour | Northern Lights in Winter](/_next/image?url=https%3A%2F%2Fwww.kaytrip.com%2Fuploads%2F2307%2Fimage%2F2307140604196468.png&w=640&q=75)


![Chasing the Northern Lights — Finland, Norway and Sweden 6-Day Tour [Small Group with Chinese-Speaking Guide] <Helsinki In, Rovaniemi Out>](/_next/image?url=https%3A%2F%2Fwww.kaytrip.com%2Fuploads%2F2310%2Fimage%2F2310310310384496.jpg&w=640&q=75)