For a balanced experience in 2026, travel experts recommend spending 3 to 5 nights specifically in the Tuscany countryside (the "Agriturismo" experience), in addition to any time spent in Florence. A 3-night stay allows you to explore the iconic rolling hills of the Val d’Orcia and visit world-class wine towns like Pienza and Montepulciano at a relaxed pace. If you stay for 5 nights, you can expand your radius to include the medieval towers of San Gimignano, the "Chianti Classico" wine route, and the thermal baths of Bagno Vignoni. Staying in the countryside is all about the "Slow Food" movement and enjoying the scenery; because many of the best villas are reached via winding "white roads," you'll want at least a few days where you aren't rushing back to a city. This duration ensures you have enough time to actually relax by a pool overlooking the vineyards after a morning of exploring hilltop hamlets.