Umbria and Tuscany: 2 days vs 3 days

Are you planning on public transportation, or will you rent a car?

Most likely will rent a car.

In my opinion, it makes more sense to choose the places you want to visit than to select one or the other province. Both are large, with many attractive sights. I would choose one base; not waste any of the short time you have with hotel changing. If Siena is high on your list, base in or near there. You will have no problem with finding plenty to see nearby in the remaining 3 or 4 days.

Rosalyn - thanks for your reply. We actually would love to see both regions...

For me the scenery is very similar. The towns are what's most interesting, so I'd pick the ones that most appeal based on a guidebook or two and a little web surfing. I'd plot them on a map and pick one in or near the center and spend all 5 nights there. I'd rather drive an extra hour or two than change rooms, especially since the distances aren't great.

I would suggest using Montepulciano as a homebase for all 5 days. It is located in Tuscany, but close the the Umbria border. This will help with not having to constantly pack and unpack every few days.

Since you will have a car, exploring both regions are easy. From Montepulciano, you can easily explore Siena, Cortona, Pienza, Montalcino, Orvieto, Arezzo, Florence, and many others. All of these are within a 1.5 hour drive and all in Tuscany. To explore Umbria from Montepulciano, you can visit Assisi, Perugia, Castiglione del Lago, Passignano sul Trasimeno (excellent seafood restaurant there), Gubbio, Deruta (great pottery), Spoleto, Todi, and many others - again all within about a 1.5 hour drive.

If you decide Montepulciano sounds like a fit, let me know and I would be happy to share accommodations and restaurants in the area.

Thanks a lot everyone for your replies!

Let me shed a bit more light onto the "issue". We have (free stay) hotel vouchers that are expiring, so we "have to" stay at two hotels. Had we not had the aforesaid "issue", we would have certainly stayed in one base. Now you know the rest of the story :).

You can do a day trip to Sienna from Florence.

Then go to Perugia or Assisi and spend more days, using one of those cities as a base.

In Rick's book "Hill Towns of Central Italy", he has a section with 3 "heart of Tuscany" drives that I plan to use when we are there. You may find it helpful too.

Siena in Tuscany and pretty Spello, Umbria, a perfect combination.

Thank you everyone for your insights.

I have five days in total before going to Rome. How should I split it? 2 days in Tuscany and 3 in Umbria or vice versa?

Anyone? TiA!