Florence to Siena, San Gimignano, Monteriggioni and Chianti Wine Region with Wine Tasting
A curated journey through medieval Tuscany, from fortified hilltop towns to rolling vineyards.
This full-day tour from Florence through Tuscany takes you across the iconic Chianti hills to four distinct destinations, combining UNESCO-listed architecture, medieval history, and an authentic wine tasting experience at a working estate.
The route is carefully designed to give travelers a broad yet meaningful introduction to the Tuscan landscape and its most celebrated towns. Each stop has its own distinct character, from the compact walled village of Monteriggioni to the grand Gothic squares of Siena.
A professional guide accompanies the group throughout the day, providing context and local knowledge at every stop. The included walking tour of Siena adds a layer of depth that independent sightseeing alone cannot replicate.
The day closes at a Chianti wine estate where the producer walks guests through the winemaking process before the tasting begins. It is a fitting conclusion to a day spent moving through one of the most historically and culturally layered regions in Italy.
Tour Highlights
Guided walking tour of Siena, a UNESCO World Heritage Site, including Piazza del Campo and the Cathedral.
Visit Monteriggioni and its remarkably intact medieval walls, one of the best-preserved fortified villages in Tuscany.
Explore San Gimignano, the UNESCO-listed town of medieval towers rising above the Tuscan skyline.
Wine tasting at a rustic Chianti estate with olive oil sampling and homemade snacks included.
Scenic coach journey through the Chianti hills with commentary from your guide throughout the day.
Free time in both San Gimignano and Siena for independent exploration of shops, viewpoints, and local streets.
Itinerary
Meet your guide at Piazzale Montelungo Bus Terminal, a short walk from Santa Maria Novella train station. Board the coach and enjoy approximately one hour of scenic driving through the Chianti hills, with your guide providing commentary along the way.
Arrive at Monteriggioni and spend one hour exploring this remarkably well-preserved medieval village, entirely enclosed within its original 13th-century walls. Stroll the cobblestone lanes, enjoy a coffee at a local bar, and take in the quiet atmosphere of a town that feels largely unchanged from its medieval origins.
A thirty-minute drive brings you to Siena, where a local professional guide leads an included walking tour of approximately one hour. The route covers Piazza del Campo, Palazzo Pubblico with its Torre del Mangia, and concludes at the Duomo, one of the finest examples of Italian Gothic architecture. Free time follows for independent exploration.
After a one-hour drive, you arrive at San Gimignano, whose fourteen surviving medieval towers are visible from a distance as the coach approaches. Your guide leads you to a panoramic viewpoint before you pass through the ancient city gates for one hour of free exploration.
A short drive from San Gimignano brings the group to a family wine estate in the Chianti countryside. Seated in a cellar tasting room, guests sample wines produced on the estate alongside olive oil and homemade snacks, while the producer explains the methods behind Chianti wine production.
The coach departs the wine estate for Florence, arriving in the early evening after approximately one hour of driving. The return journey offers a final view of the Tuscan hills as the light changes at the end of the day.
What Is Included
Included
- Air-conditioned coach transportation throughout the day
- Professional English-speaking guide for the full tour
- Local guided walking tour of Siena with a professional city guide
- Wine tasting at a Chianti estate with homemade snacks and olive oil sampling
- Entrance to Monteriggioni village
- All taxes and service fees
Not Included
- Entrance to Siena Cathedral (payable on site)
- Entrance to any optional monuments in San Gimignano
- Meals and personal beverages outside the wine tasting
- Gratuities for guides (optional and at your discretion)
- Hotel pickup and drop-off
Important Information
Book Your Tuscan Day Tour
Secure your place on this full-day journey through the medieval towns and vineyards of Tuscany, departing daily from Florence.
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