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where to stay in Tuscany?

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My husband and I, early 60s, are doing a two month European trip leaving in September. We fly into Prague and plan to take the train to Krakow, Budapest, Sofia area and then over to Croatia, Venice and on to Florence. We plan to be in Tuscany around the 17th or so of October. By that point I will want to just stay in one place for a week, perhaps rent a car, and be in the countryside.

I have found place in Chianti that has good reviews

I am thinking of booking it for a week and then heading to Cinque Terre for a couple of nights on our way to Barcelona. We are going to travel around mostly by train/bus but thought that a car may be nice for Tuscany. Any advice on that?

Is Chianti a good place to stay in Tuscany? Has anyone stayed at Romitorio di Serelle?

We were not going to book anything outside of our arrival into Prague an our last few nights before our cruise home from Barcelona. For the most part we will just decide the night before and book accordingly.

I am worried that we may not get a great place in the Tuscany area if we wait, however it is mid October so maybe it is not an issue then.

Thanks for any help on this.

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