7 days in Tuscany is the PERFECT amount of time. 2 days in Florence for art. 1 day in Siena for medieval grandeur. 2 days in Val d'Orcia for the landscape that defines Tuscany. 1 day in Chianti wine country. 1 day for a hill town you've never heard of. Car required for days 3-7. Rent on DiscoverCars →
Days 1-2: Florence. Day 1: David 8:15am → Dome climb → Mercato Centrale lunch → Uffizi 2pm → Piazzale Michelangelo sunset. Day 2: Pitti + Boboli → Oltrarno artisan workshops → Ponte Vecchio → San Miniato chant + sunset. Pick up rental car evening Day 2 or morning Day 3.
Day 3: Chianti wine road. Florence → Greve in Chianti (30 min) → Panzano (Dario Cecchini butcher-restaurant) → Chianti winery tasting (€15-30, book ahead) → Castellina or Radda → overnight in Chianti (agriturismo €80-150, Booking.com →). Day 4: Siena. Drive 30 min → Piazza del Campo (the most beautiful piazza in Italy) → Duomo (striped marble, floor mosaics) → Palazzo Pubblico → lunch (pici cacio e pepe) → San Gimignano afternoon (14 medieval towers, world champion gelato at Dondoli) → overnight Siena area.
Days 5-6: Val d'Orcia. Day 5: Siena → Montalcino (Brunello wine tasting, €15-25) → Pienza (pecorino cheese, Pope Pius II's ideal city, "balcony of Tuscany" terrace view) → Montepulciano (Vino Nobile, underground cellars). Overnight Val d'Orcia agriturismo. Day 6: SP146 cypress road at golden hour → Cortona (Under the Tuscan Sun town) → Bagno Vignoni hot spring piazza → Saturnia hot springs at sunset (free, 37°C). Day 7: Drive to Lucca (walled city, bike the ramparts) → Pisa (Leaning Tower, 30 min from Lucca) → return car at Florence/Pisa airport.
Mid-range: Car rental €40-60/day × 5 (€200-300). Accommodation €80-150/night × 7 (€560-1,050). Food €40-55/day (€280-385). Museums+tastings €80-120. Fuel+tolls €60-80. Total: ~€1,200-1,900/person.