We will spend 5 days/nights in Tuscany on our way between Bologna and Rome and am struggling with whether to stay all 5 nights at a single location that is somewhat central to the areas we want to explore, or to split between two locations for 2 and 3 nights each. The two areas are Chianti and Monalcino/Montepulciano. Would you spend a couple of nights in the Greve/Radda area and a couple in Monalcino/Montepulciano, or all 5 nights somewhere in between?
I would split it into 2 areas as you suggest.
I like your two areas, they are where we usually stay.
We like the Greve/Panzano area for Chianti. Usually stay at Vignamaggio but lots of other places to stay depending on your budget.
Montalcino/Montelpulciano gives you chance to see both of them plus Pienza. Can't go wrong with either one. We like Montalcino best, mostly because we like the Rosso/Brunello di Montalcino wine and the wine tours around Montalcino.
I would try to spend a good day in between the two places seeing Siena.
Leave Chianti area early that day and then leave Siena late in day going toward Montwhichever.
An alternative that some people like. Stay all time in Siena and go out to the different hill towns each day. Siena is very nice and quiet at night. Busy during the day. Can't really have a car in center of Siena so you would have to stay in the countryside near there or at one of the hotels just outside the walls (like Santa Caterina just south of Porto Romano).
Will you have a car? We spent a total of 7 nights in Tuscany last month. We split it up into 3 locations - 4 nights at Agriturismo Marciano just outside of Siena, 2 nights in Florence and 1 night in Lucca. If I had it to do over again, I would have spent 6 nights at the agriturismo and 1 night in Lucca (we were headed to C.T.). Agriturismo Marciano was hands down the best place we stayed in our 3 weeks in Italy. The setting was beautiful, the owners are fantastic, the rooms are very nice and the optional dinners they cook (not every night) were the best food we had on our trip. The price is VERY reasonable. You can read about them on Trip Advisor. You would need a car there, but it was a nice location for doing day trips. Have a great trip!
Agriturismo Marciano looks terrific. We will have a car and if we choose to stay all 5 nights near Sienna, it will be a strong candidate. Thanks to you and Skip for your replies.
We did exactly what you're describing for our trip to Tuscany last fall. We picked up our rental car in Bologna and spent 1 night in Lucca, 3 nights in San Albino at a small family-run Hotel I Due Cigni. It was 4 km from Montepulciano. We liked it because it was clean, reasonably priced and had a good place to park the rental car. It was a good base for touring the area.
We also spent 2 nights in Perugia where we dropped the rental car. We took the train to Orvieto from Perugia.
You could consider skipping Perugia (not our favorite town-especially with a rental car) to spend 2 nights in Orvieto and drop the rental car there.