Ciao! I'll be attending a wedding in Contignano in September. I'm looking to extend my trip with a few extra nights in Tuscany for some wine tasting and relaxation but not sure what area would be the best.
Will you have a car? that definitely impacts your areas of where you can stay. I would suggest Greve in Chianti as it is easy to get to from Florence, with several vineyards on the way there and just outside of town that also offer accommodation, so you can combine wine tasting with a vineyard stay. Take a look at Viticcio winery, they are a short walk out of town.
I also want to add: how long are you in that area? Because if just a day or two for the wedding, maybe it would be better to stay in the same area and have more time to explore it. I'd suggest heading to San Quirico d'Orcia, Pienza or Montalcino. Montalcino would be great for the views and for wine tastings, and any of them perfect for relaxation. Make sure to visit Bagno Vignoni or San Filippo, both offer outdoor hot springs!