Best Tuscan Hilltop Towns to Visit?

We hiked by this one http://www.leragnaie.it/ last October, and I recall seeing a bus stop outside. Only 2 km from Montalcino. Perhaps you can email to verify bus availability. Montalcino is quite charming.

You've pretty much answered your own questions. First, you've named many of the great hilltowns of Tuscany. All of these hilltowns can be reached by bus and some by train. I don't think that Volterra and Montalcino have train stations. I know that San Gimignano doesn't. Bus to all - yes. Second, unless you are lucky enough to get into an agritourismo farmhouse with a bus stop in the front (unlikely), you do need a car. This goes for the wineries in Tuscany as well. A rental car in Tuscany can be most handy.

Jane, technically, you can reach all of these via bus from Florence or Siena, but a car rental will make your experience much more unique. I'd also recommend staying in some of these towns overnight, vs. day-tripping them all from florence/siena. San Gimignano is one of my favorite hill towns, but it's entirely different after all the day-trippers leave at dusk, than it is in the middle of the day. To truly experience the wonderful time-trip these small hill towns offer, you need to be there when all the bus tourists have departed. Volterra offers a"real" experience as it feels very much like a real and active town vs a tourist town. San Gimignano is a close second. Haven't yet stayed in Montalcino or Montepulciano, however, we'll be scratching them off the list this May. The benefit of having the car is getting out to see wineries, and the small towns that aren't "walled hill towns" such as Castellina in Chianti, or Radda in Chianti, or any of the nearby villages, you'll need a car. For One Week, I'd recommend something like this: Day 1: Florence (sleep Florence) Day 2-3: Sienna (sleep Sienna) Day 4-5 Volterra and San Gimignano (you can stay both nights in one, and visit the other on one of the two days) Day 6 Montalcino, Pienza, and Montepulciano-- a full day, but each town is certainly doable in a day (sleep in either Montalcino or Montepulciano) Day 7: travel back to Florence (sleep in Florence) Have a great trip!

I thought Pienza was fascinatinga tiny "ideal city". The views there are great as well and we had a delicious meal at Latte di Lune. Be advised that this a small, small town and doesn't require a whole lot of time. Also, we went off season and the ducal palace and painting gallery were closedcheck ahead.

Agriturismo Cretaiole is a few km from Pienza; Montalcino and Montepulciano are easy trips from there. We loved it. Check it out.

Florence to Siena by bus is easy.
W/o a car your best base is Siena for sure. Bus to alot of great hill towns from there and do not forget San Gimignano.

I agree, San Gimignano is a must do.....

Thanks everyone!
My plan is spend my first and last nights in Florence and 5 days in Siena as my base. Will take buses to hilltowns. Should I even consider renting a car from Siena? I really don't want to deal with it...maybe hire a driver?

I drive all over Tuscany and I will tell you that I found Sienna extremely difficult to try and navigate with my car. It was confusing and parking was nonexistant where we were looking. I usually stay in other surrounding villages and would take a bus to Sienna rather than try and drive there again. However, I love driving around Tuscany and exploring on my own, but would not suggest it if its not your thing.

Siena is great as a base and has lots of bus options. If you want a tour that is personalized to a degree (small group of 8) check out http://www.toursbyroberto.com. He is one of Rick Steves' picks and has a couple of day tour options: wine, wine and history, etc.

Thanks Laurel! Will do!

FWIW I'll be staying at Agriturismo Marciano this fall in Siena. It's about a 45 min walk from the city center and a 30 min walk from the train station.

Jane Ann, You are not crazy to consider renting a car from Siena, as long as you're OK driving a stick shift. You can certainly get to the hill towns by bus from Siena, but it's far quicker by car, and you are not constrained by the hours of bus service. The net: you get more time in each town and can arrive & leave when you want. Generally speaking, there is no visitor parking within the walls of any hill town, but there are well signposted car parks outside every town. I don't drive much inside Siena either though it is easily navigable with a <$100 GPS/SatNav (or even Google Maps running on your smartphone). You can park overnight near the Fortezza. For ideas on where to go, maybe look at some photos?: http://www.lodgephoto.com/galleries/italy-tuscany-chianti/ http://www.lodgephoto.com/galleries/italy-tuscany-sangimignano/ http://www.lodgephoto.com/galleries/italy-tuscany-santantimoabbey/ Mathew