About this tour
Spend eight hours exploring two of Tuscany's premier wine regions starting from San Gimignano. You'll visit working wineries in the Chianti and Montalcino areas, tasting wines paired with local cheeses, cured meats and a sit-down lunch showcasing regional recipes. The route winds through quintessential Tuscan countryside before delivering you back to San Gimignano with time to wander Montalcino's medieval alleys and soak in views across the Crete Senesi badlands.
Highlights
- Two winery tastings with Chianti and Brunello di Montalcino wines
- Traditional Tuscan lunch with seasonal dishes and local produce
- Vineyard landscapes and rolling hills throughout the day
- Unguided exploration of Montalcino's medieval town centre
- Air-conditioned transport between locations
What to expect
Your guide collects you at Porta San Giovanni and drives into vineyard country for the first tasting, where you'll sample wines alongside cured meats and cheeses before sitting to a proper meal. The afternoon takes you deeper south towards Montalcino, stopping at another estate for more tastings paired with regional specialities. You then have a couple of hours loose in town to climb its fortress walls, duck into alleyways, or simply sit with a coffee watching the landscape roll away. Expect moderate walking on uneven medieval streets and some stair navigation at both wineries.
Good to know
Bring comfortable walking shoes and sunscreen. You'll need to manage stairs at the estates. The route isn't suitable if you have spinal issues or are pregnant. Public transport alternatives exist nearby if needed.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BugBitten summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.