Through the Vines: Wine Tastings Across the Tuscan Hills
Experiences
From the towers of San Gimignano to the cellars of Montepulciano, Tuscany’s hill towns wear their winemaking heritage lightly but unmistakably. Villa Cetinale offers an ideal base for exploring this world – close enough to reach the region’s most respected vineyards, yet tucked away enough to return to stillness. Many estates offer tastings and cellar tours, best approached with time on your side and no fixed plan.
San Gimignano’s towers set the skyline. Just outside, vineyards offer tastings of Vernaccia at small, often family-run estates, usually in simple farmhouse rooms or on terraces. Bookings are common, with straightforward pours and room to linger or keep it brief.
In Castellina in Chianti, tasting rooms sit behind stone walls. Chianti Classico is the focus, with flights or single pours depending on the producer. Visits are low-key and personal, and distances are short - easy to fold a stop or two into the day.
Further south, Montepulciano and Montalcino lean towards structure and richness. Vino Nobile di Montepulciano and Brunello di Montalcino are widely recognised; tastings often come with context from the cellar. Montepulciano’s streets slope between palazzi and tasting rooms; Montalcino rises more steeply, with broad views near the fortress. Estates sit within easy reach, and restaurants tend to give the wine list real space.
Both towns suit an afternoon visit or can anchor a day. There’s no set route - often a mix of estate tastings, a simple lunch, and time in the historic centre.
DISTANCE FROM VILLA CETINALE
San Gimignano: ~45 mins
Castellina in Chianti: ~40 mins
Montepulciano: ~1 hr 30 mins
Montalcino: ~1 hr 40 mins
WINE HIGHLIGHTS
Vernaccia di San Gimignano
Chianti Classico
Vino Nobile di Montepulciano
Brunello di Montalcino
Villa Cetinale’s house manager can help plan a day that balances wine, landscape and timing - from estate visits and tastings to local drivers and quiet places for lunch. Whether you know what you’re looking for or prefer to leave space for the unexpected, she can make it all run smoothly.
