We are traveling to Italy in October for two weeks - first time for both of us though we've traveled extensively elsewhere. We've figured out the Rome portion of our trip but then will be driving to Tuscany for the second portion (6 nights total) and I"m overwhelmed by all the options!
1. We had planned to stay 3 nights in either a Tuscan village or the countryside. After Rome, I think some peace and quiet in the country would be welcome but realize we'd be giving up the ability to walk to dinner, have more than 1 glass of wine with dinner, etc. Any strong feelings one way or another (village vs country)? We want to do some wine tasting and so may hire a driver for those days.
2. Any specific areas of Tuscany that you'd recommend for a 3 night stay? This is where I'm stuck since it all looks so fantastic.
3. We plan to spend 2 nights in Florence at the St Regis - we have starwood points and so it would be free. I'm a bit torn about this because of the plethora of villas and apartments on airbnb that seem so charming. Anyone stay at the St Regis or in that area of Florence? Would you recommend this vs staying elsewhere and taking a day trip into Florence?
Appreciate any/all comments - thanks!