1
Arrival in the hills above Montaione
Arrive via Florence or Pisa and settle into a restored estate in the hills above Montaione. The first day stays intentionally light: unpack, take a swim, and ease into the week with terrace drinks and a simple supper at your Tuscany villa.
2
San Gimignano and Vernaccia
Head out for an unhurried visit to San Gimignano, with time for the towers, the Piazza della Cisterna, and a tasting of Vernaccia at a small family cellar. In the evening, return near home for dinner at Il Caminetto, a family-run trattoria close to Montaione.
3
Chianti and the cellars
Drive into Chianti for a slow day through Greve, lunch in the piazza, and an afternoon in the vineyard cellars at Castello di Brolio or Castello di Ama. Finish with dinner at La Cantinetta di Rignana, surrounded by vines, before heading back to the villa.
4
A full day at the villa
No agenda, just the estate. Spend the day by the pool, have lunch on the terrace, read in the shade, and let the pace drop. In the evening, a private chef lights the wood-fired pizza oven for dinner at home.
5
Florence, done slowly
Take a guided day into Florence with the Duomo, the Uffizi, and lunch at Il Latini built into the plan. The pace stays measured, with time for the Oltrarno, Pitti Palace, Boboli Gardens, and dinner before an easy return.
6
Volterra and the woods of San Vivaldo
Spend the day in Volterra, exploring alabaster workshops, Roman ruins, and the old town at your own speed. On the way back, stop at Sacro Monte di San Vivaldo, a quiet woodland site that suits the slower rhythm of the week.
7
Siena with a private tour
Drive south for a guided day in Siena, including the Piazza del Campo, the Duomo, the Piccolomini Library, and a climb up the Torre del Mangia for the view. Lunch is at Osteria Il Grattacielo, followed by a calmer hour at the Fortezza Medicea before heading home.
8
Last breakfast and departure
Keep the final morning open for breakfast on the terrace, one last swim, and a quiet coffee before leaving. When it is time to go, the concierge arranges your private transfer back to Florence or Pisa airport.
