About this tour
This private 9-hour tour takes your group from Florence through two of Tuscany's finest medieval towns. You'll wander Siena's Gothic streets and iconic Campo square, then head into the rolling countryside to Montalcino, perched on its hilltop fortress. The real draw is stopping at a working winery in the Brunello vineyard region—you'll tour the cellars and taste wines where they're made, with the option to eat lunch surrounded by vineyards. A driver who knows these backroads intimately handles navigation while sharing local stories.
Highlights
- Siena's Gothic architecture and famous Campo square
- Montalcino hilltop fortress and medieval streets
- Private cellar visit at a Brunello winery
- Wine tasting direct from the producer
- Optional winery lunch with vineyard views
- Driver shares Tuscan history and traditions
- Hotel pickup and drop-off included
What to expect
Your driver collects you from your Florence hotel and heads south toward Siena. You'll have time to explore the medieval town centre on foot—the Campo is unmissable, a sloped piazza ringed with terracotta-coloured buildings. From there, the drive continues through vine-covered hills toward Montalcino. The town itself is compact; the fourteenth-century fortress dominates the skyline. The highlight is your winery stop: you'll walk through actual production cellars, see the aging process, and taste their Brunello wines. Lunch can happen here if you choose, served amid the vineyard landscape. The drive back to Florence winds through classic Tuscan terrain.
Good to know
Lunch and wine tastings are separate costs. Wear comfortable walking shoes for cobbled streets and uneven fortress grounds. The driver speaks English but isn't a licensed city guide, so don't expect detailed art-historical commentary. Infant seats and prams are available 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.