Tuscan hilltowns itinerary

kbm,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

You can easily spent two days in Siena. You can combine Montalcino and Montepulciano in the same day, both are very small towns. San Gimignano is wonderful and you can spend an entire day there. I wouldn't take any time from Rome but if you can add a day to your trip you could add it to Tuscany.

Donna

I don't really think of Siena as a hill town; it's a hub with enough to keep you busy for a few days.

When I went to Tuscany, I used Siena as a base for exploring hilltowns. The first day I just explored Siena. Then I rented a car for the two days; Day Two I went south toward Montalcino, Pienza, Montepulciano, and environs. Day Three I went to Volterra and San Gimignano. This worked well for me, and I still had evenings to enjoy in Siena.

I recommend stopping at places other than the most well-known hill towns. I enjoyed stopping at Bagno Vignoni and at the Abbey of Sant'Antimo. But the map is speckled with things to see, so keep it loose and flexible.

Even for a non art lover, I think you will need 2 nights in Florence, giving you one full day for the sights.
Are you travelling Venice ==> Rome ==> Florence/Tuscany ? If so, this is unnecessary backtracking.

Days 1-3 Venice
Day 4 Train Venice to Florence
Day 5 Florence
Day 6 Train Florence to Siena (early am)
Day 7 Pick up car in Siena (early am) and day excursion to Sam Gimignano and Volterra
Day 8 Drive to Orvieto (via Montepulciano and Montalcino)
Day 9 Return car in Orvieto (early am) and train to Rome later in the day
Days 10-13 Rome
Day 14 Depart

Or even a day less in Rome, and make a day excursion to Lucca from Florence (by train).

I have been to all of the suggested towns but have not seen Cortona mentioned,we stayed four nights there and explored the towns in that region,they are all unique in their own way.
Mike

Orvieto is in Umbria, also a beautiful area.

Thank you for the suggestions! I am only going to Florence because in my previous posts it was suggested that I take the train from Florence to Milan on the day of our departure rather than from Rome to Milan. (We are flying into and out of Milan.) Otherwise, we would probably skip Florence entirely as there are other places that interest us more. I think we will keep the number of nights we had originally planned for Rome and Tuscany. Lane, that itinerary sounds great! I was thinking that an agriturismo near Siena might make the most sense. I would also like to see Cortona, but I'm not sure that we'll have time to with only a few days.

Personally, I would be in the town of departure the night before a long flight. You never know what type of transportation issues can arise. There could be a train strike or other factors that prevent you from catching your flight. I would rearrange your schedule to be back in Milan the night before your flight to be safe.

Donna

Absolutely be in the town of departure the night before a high stakes flight. Stuff happens. It has happened to us (like late trains, auto accidents, late planes -- travel long enough and it all happens sooner or later)

We have done Tuscan trips 3 times. 35 years ago for a week near Siena; 15 years ago for a week near Lucignano and two years ago for two weeks in Montepulciano.

We based in an apartment each time and then did day trips from our base. I would not use an agriturisimo. It is so much nicer IMHO to be based in a hilltown with parking so you have restaurants to walk to each evening (drunk driving laws are VERY tight in Italy) rather than being in the countryside where you have to drive everywhere.

I would also not necessarily try to cram in 2 towns a day. They get sameish. We loved Volterra and Lucca -- very different. You could combine San Gimignano and Volterra. Siena may be my favorite town in Italy and it repays a full day visit. The historic center is ringed with parking garages. Climb the Torre Mangia (https://janettravels.wordpress.com/2011/09/18/climbing-the-torre-mangia-at-67/) and spend some time in the absolutely stunning Cathedral. This one would be #1 on the list. Montepulciano is an enchanting town with lovely views onto the Val d'Orcia and the Val d'Chiana. There is tourist parking outside the walls. (tourist parking is quite well signed at the hill towns, you may have to search for space but it will be clear where to go) Another wonderful visit is Monte Oliveto Maggiore Abbey. The views driving in this area are amazing. The gardens of La Foce are open Weds afternoons (check in case these things change). If you are in the area at that time, definitely a wonderful visit. https://janettravels.wordpress.com/2011/09/19/la-foce-in-the-heart-of-the-val-dorcia-2/

Less is more. Pick your targets, arrange them by area and variety -- we liked doing quite different places e.g. the abbey, Siena, Montepulciano, Lucca. It is more interesting to spend some time in a place than to rush to three similar places.