Experience a private Tuscany tour from Rome to Florence, with visits to medieval towns like Siena and San Gimignano, and a wine tasting in the Chianti region.
Experience a private Tuscany tour from Rome to Florence, with visits to medieval towns like Siena and San Gimignano, and a wine tasting in the Chianti region.
- Siena - Begin your journey in Siena, celebrated as a living example of a medieval city. Marvel at the Cathedral and the main square, Piazza del Campo, a unique urban space with its shell shape, historically the hub for political and commercial activities in the ancient Sienese Republic. It is also the venue for the renowned Palio delle Contrade…
- Siena - Begin your journey in Siena, celebrated as a living example of a medieval city. Marvel at the Cathedral and the main square, Piazza del Campo, a unique urban space with its shell shape, historically the hub for political and commercial activities in the ancient Sienese Republic. It is also the venue for the renowned Palio delle Contrade horse race, held twice annually.
- Piazza del Campo - At the heart of Siena lies its distinctive square, the grand Piazza del Campo, where you can enjoy a leisurely walk and soak in the scenery.
- Chianti Road - Besides the stunning views of vineyards and olive groves, Chianti is famous among tourists for its abbeys, villas, castles, wineries, and restaurants. This makes the journey a magnificent path through Tuscany, offering views of hills adorned with vineyards, olive trees, quaint villages, and unique bell towers.
However, for Italians, “Chianti” primarily signifies excellent wine! Therefore, during the trip, your driver/guide will prepare you for the wine tastings scheduled for this day-tour. With hundreds of wineries and farmhouses in this Tuscan region, your local driver will select those that match your preferences. (NOTE: Wine tasting/paired lunch is payable on-site, with prices ranging from “free of charge” to 50 Euros or more, depending on the winery and tasting type.)
- San Gimignano - Upon reaching San Gimignano, admire the iconic skyline featuring 13 medieval towers. Bathed in the warm glow of mid-morning sunlight, the town’s ancient towers and crenellated walls cast long shadows over the surrounding landscape. Must-see highlights include Piazza della Cisterna, named after the well at its center and surrounded by pristine 13th and 14th-century palaces, and the Piazza del Duomo (Cathedral). Step inside the magnificent 12th-century Romanesque church for breathtaking interior views. Numerous shops line Via San Giovanni and Via San Matteo.

- Private tour
- Driver at disposal full day
- Transport by air-conditioned minivan
- Alcoholic beverages
- All taxes, fees, road tolls, fuel
- Private tour
- Driver at disposal full day
- Transport by air-conditioned minivan
- Alcoholic beverages
- All taxes, fees, road tolls, fuel
- Gratuities
- Gratuities
Why settle for just planning a transfer when you can experience a Smart Transfer? On the journey to Florence, enjoy the breathtaking Tuscan countryside, with opportunities to stop for lunch and/or wine tasting at a genuine local winery. You can also explore renowned medieval towns like Siena and San Gimignano (the itinerary is flexible to suit your…
Why settle for just planning a transfer when you can experience a Smart Transfer? On the journey to Florence, enjoy the breathtaking Tuscan countryside, with opportunities to stop for lunch and/or wine tasting at a genuine local winery. You can also explore renowned medieval towns like Siena and San Gimignano (the itinerary is flexible to suit your preferences!).
Siena, located in Tuscany, enchants visitors with its medieval allure, celebrated as one of Italy’s most captivating destinations due to its historical splendor and cultural depth.
San Gimignano, set amidst the picturesque landscape of Tuscany, showcases medieval grandeur. Known as the “Manhattan of the Middle Ages,” its skyline is adorned with ancient towers, each reflecting its rich heritage.
At the heart of Tuscany is the Chianti region, famous for producing some of Italy’s finest wines. This tour offers the chance to savor wine tastings at their origin, uncovering the secrets that make them truly exceptional.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.