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        Sunset panorama of Siena’s historic center in the Province of Siena, Tuscany, with the Siena Cathedral and medieval skyline overlooking the Tuscan hills.

        Province of Siena

          Explore Tours

          Close-up of historic Sant'Antimo Abbey under a dramatic sky, a key site for Montalcino wine and gourmet tours.

           Florence, Italy

          Val d'Orcia Full-Day Guided Tour from Florence with Wine

          Trade the city for cypress hills and ancient cellars — one unforgettable day through Val d'Orcia, tasting the wines that made Tuscany legendary.

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          From € 46.00
          Breathtaking panorama of San Gimignano's medieval towers surrounded by verdant Tuscan countryside.

           Rome, Italy

          Siena & San Gimignano Day Trip from Rome with Wine Tasting

          From Rome's streets to Tuscany's medieval hilltops in a single day — two UNESCO cities, eight wines, and flavours you will not forget.

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          From € 260.00
          Historic stone towers of San Gimignano under a clear blue sky, showcasing medieval architecture in Tuscany.

           Florence, Italy

          Florence to San Gimignano: Half-Day Tour with Wine Tasting

          Climb ancient towers, wander cobblestone streets, and toast to Tuscany with a glass of Vernaccia in the hills — all in one unforgettable morning from Florence.

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          From € 55.00
          Ripe Sangiovese grape clusters on vines in a Chianti vineyard, featured on a private Tuscany wine tasting and lunch tour

           Florence, Italy

          Private Chianti Tour: Wine Tasting, Lunch & San Gimignano

          Roll through cypress-lined hills, climb a medieval tower, and toast Tuscany at a vineyard table reserved just for you — this private Chianti escape is the day trip Florence was made for.

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          From € 100.00
          Venice Rialto Bridge over the Grand Canal, highlight of 10-day private Italy tour from Rome to Venice

           Rome, Italy

          Italy Grand Tour: 10-Day Private Trip Rome to Milan

          Ten days, one luxury vehicle, and a private guide — discover Italy's greatest cities and hidden hilltop villages without a single logistical worry.

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          From € 2624.00
          Traditional olive oil mill with stone press and bottle in scenic Chianciano town square.

           Chianciano Terme, Italy

          Olive Oil & Food Tasting Tour at a Mill in Chianciano

          Step inside a working Tuscan olive mill and taste the liquid gold that has defined this region for centuries. A one-hour journey from grove to table that you will not find on any typical itinerary.

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          From € 30.00
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          More to know about Province of Siena

          Siena Province, located in central Tuscany, Italy, encompasses rolling countryside and medieval towns. The provincial capital, Siena, features the stunning Gothic cathedral and the famous Palio horse race held in Piazza del Campo. Visitors explore Renaissance art in museums, wander through hilltop villages like Montepulciano and Pienza, and sample local Brunello wine in historic cellars.
          The Province of Siena is an administrative province in southern Tuscany, Italy, encompassing the city of Siena and surrounding municipalities including Montalcino, Pienza, San Gimignano, and Montepulciano. The territory contains two UNESCO World Heritage Sites: the historic centre of Siena and the Val d'Orcia landscape. It is recognized internationally for its medieval architecture, Sangiovese-based wine appellations, and well-preserved rural countryside.
          Destination | Province | Tuscany | Italy | UNESCO | Wine Country | Medieval Heritage | Rural Tourism