Tuscany is an entire vacation, not a day trip. Florence alone deserves 3 days. Chianti wine country: 2 days. Val d'Orcia (Pienza, Montalcino, Montepulciano): 2 days. The hill towns (San Gimignano, Volterra, Cortona): 1-2 days each. The coast (Maremma, Elba): 2-3 days. The minimum: 5 days (Florence + one area). The ideal: 7-10 days. The dream: 14 days (the full Grand Tour Tuscany).
Plan my Tuscany trip →Days 1-3: Florence. Day 1: Duomo area, Piazza della Signoria, Ponte Vecchio, Oltrarno evening. Day 2: Uffizi (morning), Accademia/David (afternoon), San Lorenzo market. Day 3: Palazzo Pitti + Boboli Gardens, Santo Spirito, final Florence evening. Days 4-5: Chianti (rent a car or join a tour). Drive the Chiantigiana (SS222). Stop at 2-3 wineries (Antinori, Castello di Fonterutoli, etc.). Visit Greve in Chianti (Tuesday market), Panzano (Dario Cecchini — the famous butcher). Stay in a Chianti agriturismo. This is the minimum-viable Tuscany.
Days 1-3: Florence (as above). Days 4-5: Chianti (as above, stay overnight at agriturismo). Days 6-7: Val d'Orcia (drive south from Chianti, 1.5h). Day 6: Pienza (pecorino tasting, the "ideal Renaissance city"), Montepulciano (Vino Nobile tasting, Piazza Grande). Day 7: Montalcino (Brunello at the fortress enoteca), Bagno Vignoni (the thermal piazza), the iconic cypress road of Val d'Orcia. This is the classic Tuscany experience — art + wine + landscape + food + the light.
Days 1-3: Florence. Days 4-5: Chianti. Days 6-7: Val d'Orcia. Day 8: Siena (a full day — the Campo, the Duomo, the contrade streets, the Palio atmosphere). Day 9: San Gimignano + Volterra (the towers + the Etruscan hilltop). Day 10: Lucca (the walled city — cycle the walls, Torre Guinigi, Piazza dell'Anfiteatro). Day 11: Pisa (morning, combine with Lucca). Days 12-14: Maremma coast or Elba. Maremma: wild Tuscany (Castiglione della Pescaia, Parco della Maremma, Pitigliano the "little Jerusalem"). Elba: the island (Napoleon's exile, beaches, snorkeling, the ferry from Piombino). 14 days is the FULL Tuscany — and you'll still miss Arezzo, Cortona, Garfagnana, Mugello, the Crete Senesi... Tuscany is inexhaustible. Day trips from Florence →