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anidel
Me and the Mrs tend to go pretty lux, as we sort of treat it as our annual holiday. We've stayed at the Spaltenna in Gaiolie, which is superb, and at the Relais di Vignale (or similar) in Radda, which is also excellent.
For me, food and wine are probably greater passions than cycling, so I go full on in Tuscany. To that extent, I think Radda is a better bet that Gaiolie, and the roll down to the start is really no problem.
Last year, we decided to Air B'n'B an apartment, rather than stay in a hotel, and we really lucked out with a great apartment in the centre of Gaiolie, maybe 200 yards from the start. It was so perfect, we booked it for 2018 while we were there.
Having said all that, first time we went we stayed in a tiny apartment miles away, and still has a great time.
I have yet to have a bad experience in Tuscany.