Originally Posted by
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I just want to say that I really appreciate the thoughtfulness that you are both putting into my question and your suggestions have been helpful. And since you're still willing to make recommendations, I can try to be more specific.
And so you know more about me, I have travelled a pretty good amount and I can be happy with accomodations that range from $10/night is southeast Asia, to Oberoi or St. Regis level luxury. I'm game for anything (as long as it's clean and safe), but I also understand the limitations of any given trip. I don't necessarily prefer one or the other - it is dependent on where I am going. In Italy, I'm not looking to spend all day on the property, but I do want it to be comfortable and if we decide we need some down time, we can relax at the hotel.
So for the time in the Tuscan countryside -
I'm less interested in a home rental situation because I don't want to feel like I should be cooking or anything like that, which is how I feel when there is a kitchen. A comfortable place to sleep, not too frou-frou. It doesn't have to have a restaurant on site but places to eat and drink within walking distance would be a plus.
As far as activities - they would be limited to good food and wine and enjoying the view. We plan to be more active with museums, a bicycle tour, maybe a food or cooking tour/class while in Florence.
In reading about the different towns in the guide books and looking at the various lodging options, we're finding it a bit overwhelming to narrow it down - hence this post!
I think that based on the activities you like, you should consider a smaller inn or B&B in a Tuscan town, as opposed to a full blown resort that is self-contained and not within walking distance of a town/village. That way you can relax on the terrace, or be out at a restaurant, sitting at a caffe, riding a bike, or whatever else. I like Perche's suggestion of Montepulciano and Siena. You might also like San Gimignano. My advice when wanting to be outside of the city is to research a town that seems interesting to you, then try to find accommodations. If you decide on a town, maybe I can help find someplace to stay.
As far as Florence goes, if you don't have that planned, I can be more helpful with that. I make it there once a year and can give you some specific guidance.