A week in Tuscany works best when the villa is the hub and cities are the spokes. This itinerary assumes a countryside base in Chianti or the Florence hills, with one Val d’Orcia day and enough unscheduled air to actually rest.

Day 1 — Arrive and settle

Land, transfer, unpack slowly. Walk the garden before you open a map. The first evening should be at the house—private chef or a simple market supper—so the trip begins with place, not logistics.

Day 2 — Florence on your terms

One focused city day beats three exhausted ones. Choose a museum block (Uffizi or Accademia), a neighbourhood lunch, and an early return. From a Florence Hills or Chianti villa, you can be back under olives for aperitivo.

Day 3 — Chianti towns & a cellar

Loop Greve, Radda, or Castellina with one serious tasting. Keep the afternoon light: a ridge walk, a nap, a courtyard dinner. This is the day many guests remember as “why we rented a villa.”

Day 4 — Soft day at the estate

Protect a full day with no tickets. Swim, read, cook, or take a short drive to a neighbouring village market. Concierge experiences—truffle walks in season, a chef’s lunch—fit here without overcrowding the week.

Day 5 — Val d’Orcia

Leave early for Pienza and the open hills. Photograph while mist still holds the valley, taste pecorino, and decide whether Montalcino deserves a cellar stop or a belvedere-only pass. Return for a late supper at the villa.

Day 6 — Siena or Lucca (choose one)

Siena suits Gothic drama and the Campo; Lucca suits walls, bicycles, and a gentler urban pace. Pick based on energy, not FOMO. Either city is richer when it is the week’s only major urban add-on after Florence.

Day 7 — Departure buffer

Keep the final morning empty. A last espresso on the loggia beats a panicked shop stop. If your flight is late, add a short olive-oil mill visit near the house—not another marathon.

Where to base the week

Chianti maximises wine-country immersion with Florence access. Florence Hills prioritises art days. Val d’Orcia bases suit slower, more pastoral weeks—but lengthen drives to Florence. Browse our destination pages before you fix the map.

Ready to match the itinerary to a house? Explore Tuscany villa rentals or browse ChiantiVal d’OrciaFlorence Hills.