Both are Tuscany. Both have cypress trees. They look completely different.
Plan your trip →UNESCO-listed landscape. Open, golden, lunar in parts. Pienza, Montalcino, Bagno Vignoni thermal. The famous lone-cypress-on-a-hill photos. Brunello.
More intimate, more green. Rolling vine rows, stone villages, closer to Florence. The Chiantigiana road (SS222) is the classic drive. Chianti Classico + olive oil.
Val d’Orcia: the landscape IS the attraction. Photography, driving, thermal baths. Chianti: wine tasting is the attraction. Cellar visits, vineyard lunches, closer to Florence. 3 days: do both (they’re adjacent).