Dear Paul,
for your nights in Florence, take a look at this page where you'll find a selected list of traditional hotels in Florence with a map, so you may choose according to the location where you would like to stay in:
http://www.tuscanyaccommodation.com/florence-hotels/
Then, you'll move to Pisa and Lucca for the third day, but I'd rather spend a night there instead driving straight away to the Chianti region. Consider that it takes you about 1 hour - by car - from Florence to Pisa or Lucca; then, hal an hour from Lucca to Pisa - or viceversa - and a half day to visit at least the MUST SEES of both cities. Then, again about an hour to come back to Florence, where you should continue to the Chianti region...a bit overfull I think! So, I would spend a night in
Pisa or
Lucca (yake a look at the city hotels selected) and then move to Chianti fully rested early in the morning.
Spending at least two nights in
Chianti is a good idea: you won't have to change hotel and location each night, it's a bit more restful.
For the last two nights you could choose a location in
Valdorcia, even if you would be sourrounded by the countryside: it's a marvellous location and the small towns like Castiglione and San Quirico d'Orcia, PIenza, Montalcino and Montepulciano are really precious.
Then, last day to Cortona and Arezzo, before going to Rome and flying back home.
I don't know when you need to arrive at Rome, but if your flight leaves early in the day, maybe it's better spending the two last nights in
Cortona, so that the last itinerary step will be more calm and easy to afford.
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