Tuscany - Umbria where to stay

To split the stay between Siena surroundings and Montepulciano doesn't make much sense to me. The two are very close to each other, therefore moving base from one to the other would be a waste of time.

There would be value however to split your stay into two locations, one in Tuscany and one in Umbria, since visiting both from one location only is somewhat of a challenge, since the distances start to become too long and too much time would go into driving. For example if you chose to stay near Siena and wanted to visit Gubbio or Spoleto in Umbria, it would be a 2 to 2.5 hour drive each. I like day trips that aren't over 1 hr or max 1.5 hour each way, because driving too much 6 days in a row becomes tiring.

Which base to choose in Tuscany depends a lot on which places you want to visit. I like the area near Siena or just north of it (near Monteriggioni for example), along the freeway to Florence, because that puts you within one hour drive of everything famous in Tuscany. From that area Florence, Chianti Hills, San Gimignano, Certaldo, Volterra, Colle VE, Monteriggioni, Montalcino, San Quirico, Buonconvento, Pienza, Bagno Vignoni, Montepulciano, Cortona, etc. are all within 1 hour drive.

The area near Montepulciano is good for Montalcino, San Quirico, Buonconvento, Pienza, Bagno Vignoni, Montepulciano, Cortona. But Montepulciano is somewhat inconvenient for the Florence area as it's south in the Siena province.

If you intend to visit Umbria, the most famous places are: Perugia, Assisi, Gubbio, Spello, Spoleto, Norcia, Todi, Orvieto.

Where you want to base yourself for visiting Umbria also depends on which of the above places you want to visit. Orvieto is a bit decentralized as it is in the southern edge of the region closer to Latium, however the area around Assisi/Spello would probably provide the most central area to visit all others. Both Assisi and Spello are beautiful towns in themselves anyway. Orvieto from there is over 1.5 hours, so you might still be able to visit in a day trip from there. Or better yet, you can visit Orvieto on your way down to Rome (you can return the car there, but only with Hertz).

A couple of years ago two friends and I spent a few days based in Siena and a few days based in Assisi, we were able to find centrally-located hotels with parking onsite or nearby.

Thank you for the great information. Keep it coming.
OK so we have 7 nights total in Tuscany/Umbria. We don't want to spread ourselves thin so are we better just staying near/outside Siena and staying in Tuscany the entire time, or would we really be missing something if we did not spend some time heading over to Umbria, basing ourselves there and exploring some of that area? Without having been there it's a tough decision to make - we want to explore but don't want to spread ourselves too thin, and we don't want to miss anything fabulous.
Also, we do plan to spend our last day in Orvieto before boarding a train to Rome.
Question: Lake Trasimino- see it or skip it?
Question: Anyone know a castle to stay in near central Umbria where we can explore a few towns of Umbria?

Forgot to add - in Umbria - what's better - the "popular" places, or the "off the beaten path" places?

With just 7 nights (6 days?), I wouldn't make any special effort to see Lake Trasimeno. There are so many much more compelling places in Tuscany and Umbria. That being said, however, if you base yourself near the lake, you can easily do day trips to many of the wonderful nearby towns. Roberto makes a good point about driving fatigue; however, you have to balance that off against the time lost when you move. Note that there is a train station in Chiusi from which you can get to Siena and Florence. It's inadvisable to drive to either of them because of the prevalence of ztl's. Staying near Chiusi would also be a good choice because it's so close to the A1. The area is just loaded with agriturimos and b&bs.

Thank you Rosalyn
I think i am going to lose my mind. Many have said to not drive to Siena or Florence, and many more say just park outside the city and you are fine. I hate paying to have a rental car sit at our B&B while we pay to take a train, and then we also lose out on the opportunity to see other things en route. It has been overwhelming trying to plan our trip - this region is only one of our stops.
With a car i did not think it would be that challenging to check out of one B&B and into another.

Roberto thank you for your helpful advice on Tuscany/Umbria. We would like to spend some time in Umbria because of what i have heard and read.
If we wish to see Perugia, Spello, Spoleto, what town would you recommend basing in that is not terribly far from Monteriggione so that we do not lose too much time relocating?
Also, what are your thoughts on visiting the Ferrentilla Mummies? Worth it???

Spello is just a few kilometers (one train stop) from Assisi. Todi, Gubbio, Assisi, Spello are all places I would recommend in Umbria. Umbria is a little less tame than Tuscany in terms of landscape.

Monteriggioni is very close to Siena.

My friends and I had a car, we visited Montepulciano, Montalcino, Siena, Monteriggione, San Gimignano, Volterra, Pienza, Sansepolcro, Anghiari and Arezzo from Siena; Assisi, Deruta, Spello, Todi, and Gubbio from Assisi. We had 11 nights altogether.

Thank you Zoi - that is very helpful.
Did you DRIVE to the city of Siena??? If so would you avoid it if you had to do it again? I know the hilltowns and areas outside the cities are fine for driving. We are just trying to decide on car vs. no car. We want freedome but don't want to make a huge mistake.

Zoe
What do you mean "a little less tame" in terms of landscape? It is more or less dramatic - and should we do both or just spend more time in one region?

I think splitting your stay with 4 nights in Tuscany (near Siena) and 3 in Umbria (near Assisi or Spello, which are near each other) would be good. It's hard to visit both Tuscany and Umbria from one location only. But if you did that, I would probably choose a location (maybe an agriturismo) between Siena and Bettolle. That would be central to Eastern Tuscany and Umbria.

If you stay near Siena, I would suggest to drive to Siena and park at the Fortezza parking lot (near the stadium). Florence, if you decide to take a day trip there, it's probably faster by train from Terontola (if you stay near Bettolle). If you are staying near Siena, then I would drive to Florence and park near the Porta Romana. Going all the way to Chiusi or Terontola from Siena, to take the train to Florence is a lot of extra detour. Then it's better to drive to the Siena train station and park in the parking structure there and proceed by train to Florence (90 min ride from Siena).

Regarding the landscape of Tuscany and Umbria, they are very similar. Lot's of hills and mountains in both places, with some small flat river valleys and canyons in between.

Thank you Roberto
Your help is invaluable. If there is not a huge difference between Tuscany and Umbria (i thought there was), then maybe better to stay 6 nights in one central area and add 1 more night to Rome (we only have 3 nights in Rome)??? I will check out the town you recommended for a base and look for an Agriturismo. We want to be reasonably close to the wine country since we plan to do some tours and tastings in Montelcino and Chianti!!

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

We did drive to Siena, stayed at Hotel Minerva on via Garibaldi near one of the city gates, parking was in a covered garage onsite. Every day we drove to one or two hill towns. Then we moved to Assisi, parked near the Rocca Maggiore and walked down a flight of steps to our B&B, but there are several,garages in the area. We visited one or two hill towns every day from there as well.

By less tame, I mean a little more dramatic in landscape, definitely different from Tuscany but in a subtle way. Hills are a little steeper. Food is more mountain-game-based.

However you split your time, both regions are beautiful.

"I hate paying to have a rental car sit at our B&B while we pay to take a train"

Don't forget that if you drive into a ZTL, even accidentally and even if only for a short distance, it will cost you a LOT more than the train tickets! You'll first get a charge from your rental car company for turning over your information to the authorities, then (months later) you'll get the ticket itself - and it's something like €100, per infraction (so if you get lost or turned around and enter the ZTL three times in 10 minutes, you get 3 separate tickets).

Florence and Siena have particularly troublesome ZTL's, and you must get EXACT directions on where to park to avoid them and still not be too far from the cities. Also, the ZTL's are large, so you can't just walk into the center from the parking lot, as you can in smaller towns like Spello.

If you are aware of and prepared for the pitfalls, you can drive to these cities. But many find it's less hassle to take a train or bus there, and not have any worry.

On our last trip to Italy, we spent a week in a villa outside Vico D'Elsa and a glorious week high above Lake Trasimeno, and both locations were wonderful, but I agree with others that with only 7 nights, would choose either Tuscany or Umbria. I found driving to the edge of Sienna and parking was easy, and no trouble to see the whole city on foot. Driving into Florence was much more stressful due to traffic, although we easily found parking at the Porta Romana (which is very cool) and spent a nice if very crowded day there. After that experience, I vowed never to try and visit major cities for the day by car, because it's hard to enjoy them in short bursts of time, and day trippers really make the major tourist sites unbelievably crowded, and without a home in the city, there is no respite. Personally, I would split your time by spend ing 2-3 nights in Florence at the beginning, then pick up a car when you leave, spend your other 4-5 nights at one location in the country, driving to the towns you wish to visit. Your plan to drop off in Orvieto is a good one (if you can get a decent rate from Hertz) since that's a lovely place to visit (the funicular is really fun for kids) and an easy train ride into Rome. The one caution I would add for a driving trip, is that if you are into food and wine (and who isn't!!) you need to plan somewhat carefully. I am an intrepid driver in Europe, but strongly prefer not to take long rides in the dark, and certainly would not drive after drinking (anytime, anywhere but particularly not on winding dark Tuscan roads), so you want to make sure that there are enough dinner options close to your location. We visited many lovely restaurants for lunch, then stayed in the town late in the afternoon, and made simple meals at our villa for dinner (our group had 4 adults and 6 kids, so this might not work for you). No matter what you choose, you will have a glorious trip, as there are so many fantastic places to experience.

SOOO much great information = Thank you
Has anyone ever stayed in Bettolle? It's an easy 30-50 minutes to almost everywhere in Tuscany AND Umbria (Siena, Florence, Perugia, Orvietto, Spello, Montalcino. And walking distance to a little town with restaurants/pubs and grocery.

I just want to underscore the very good point made above by Rachel. Choose your lodgiing location(s) carefully. Dinner usually isn't available in Italian restaurants before 7:30 at the earliest; so it's prudent to be in or near a town with restaurants. Alternatively, some agriturismos offer a dinner option. By "near," I mean a few minutes drive. Tuscan distances can be deceptive. A short distance on a hilly, winding road, after dark, can take more time than you imagine. The designated driver would also have to forego imbibing in that fabulous Tuscan wine.

The more i read the more confused i get. We have changed our plans now at least a dozen times and i feel like i am back at the drawing board. I thought staying somewhere central and branching out each day in a different direction would be fun to see different hilltowns. Now i am thinking we should have just done a cruise for simplicity sakes. Planning a trip blindly to a country you have never been to is mind boggling.

The more i read the more confused i get. We have changed our plans now at least a dozen times and i feel like i am back at the drawing board. I thought staying somewhere central and branching out each day in a different direction would be fun to see different hilltowns. Now i am thinking we should have just done a cruise for simplicity sakes. Planning a trip blindly to a country you have never been to is mind boggling.

Forget a cruise. You can't see Tuscany and Umbria from a cruise. The most interesting parts of both regions are well inland and not easily reachable from the coast. Umbria is landlocked anyway.

I gave you several possible locations to visit in both regions. You just have to decide which places you want to visit, plot them on a map, and decide on a base(s) that is central enough to drive to those locations. If you want to devote anything more that half a day to Florence, I suggest you stay two nights in Florence, then on your way out, rent a car and spend 5 nights in the countryside. The area near Siena is the most central to both Tuscany and Umbria.
From that area you are within 1 hr to most famous Tuscan locations. Umbria is a bit farther, but Assisi, Perugia and Spello, for example, are within 1.5 hour drive. Gubbio and Spoleto are farther (at least 2 to 2.5 hours) but still doable.

So this is what you should do in my opinion:
FLORENCE: 2 nights.
That will give you a full day dawn to night to visit Florence (at least some). Certainly more than just a few hours on a day trip from Siena.
(rent a car on your way out from Florence and go to near Siena)
SIENA AREA: 5 nights.
I don't recommend to stay in Siena city center with a car, because of severe traffic restrictions (like Florence). Choose a location out of town, in a small town or countryside. The important thing is that base is close to the freeways' entrances. There are 3 main freeways in that area:
SIENA-FLORENCE
SIENA-BETTOLLE-PERUGIA
FLORENCE-ROME (which crosses the SIENA-BETTOLLE-PERUGIA at Bettolle).

Choose a B&B or Agriturismo (farmhouse) that is close enough to the freeway entrance. Don't trust your eyes, because Tuscan roads can be deceiving and, except for the freeways, you won't be able to sustain an average speed over 40 km/h (25 mph). Once you find lodging you like, use the Google Maps Directions feature to find how long it takes to the closest freeway entrance. Limit country road driving at night. Those roads are dark, not always well signaled, curvy and often narrow. Not ideal after a long day driving on a day trip. So the closer your lodging is to a freeway entrance or major highway, the less you will stress at the wheel when you return at night. Some farmhouses, although beautiful, may involve a driveway on dirt roads, often a long distance from the highway.
You can use Google Maps to locate something. Take a look at this one. At the edges of the city of Siena, right next to the freeway entrance:
http://www.tufihotel.it/?page_id=656&lang=en

All you have to do is go to Google Maps, zoom in the general area where you want to stay then enter in the search box:
HOTELS
A lot of hotels will pop up on the map. Just click on them, go to their website till you find what you like.
If you prefer a farmhouse, in the search box enter:
AGRITURISMO
A lot of agriturismo will pop up on the map. Just click on some. There are websites for each. Just take a look and take a chance.
You can also try the following websites:
booking.com
venere.com
agriturismo.it
agriturismo.com
agriturismo.net

Just make sure that you locate the place on the map exactly. You want to make sure it's not too secluded and hard to reach from the freeways. Then when you see something you seem to like, just take a chance. Some of the best accommodations are found by chance. You can't always rely on Rick Steves' people for advice. Otherwise you'll limit yourself to the handful of locations always suggested here (which are always booked months in advance).

Hi Roberto
Thank you for all the awesome information. Yes we have been on ALL of these sites - that is why i am so overwhelmed. I never thought it would be so challenging and i guess that is because we are unfamiliar with the area. We want to do a day trip to Siena, Greve in Chianti (or Castillione in Chiante), Montalcino/Montepulciano, Florence (via train), and we were hoping to get over toward Umbria which is why we thought staying further east of Siena would be good, but we don't know the towns and don't want to end up staying 6 nights in some place that is a bad decision. Since we plan to do wine tasting we don't want to be that far of a drive from the wine region so we have a challenge. Our last day when we head out will be to Orvietto to tour and then drop off car and train to Rome.

I just really need advice on a central area now that we have decided it's too much trouble to split our time 3 days Tuscany/3 days Umbria and now we are not sure which of the two to do, or where to hub. We can find a farmhouse once we know where to stay.
Anyone know anything about Bettolle?
Also, are we going to run into parking problems, costs and restricted areas in every hilltown we visit? Starting to rethink our entire trip - the comment about the cruise was a joke (as in forget Italy entirely and just book a cruise anywhere not to have to go thru this planning torture).

Driving in hill towns is not a problem, you just don't do it. Ever. There are garages around the towns, or parking lots, use those. You'll be fine.

No, we didn't drive in Siena itself, our hotel (with parking) was ten minutes' walk from the Campo.

Zoe - you don't do what ever??

I think Zoe means don't drive into the center of the hill town, just to the outside and park in a public lot and walk into the center. I have done this, and find the signs easy to follow. Most of the lots have a machine where you enter your license plate number and pay for as much time as you plan to stay. Not particularly expensive, but if it's not a free lot, do pay to avoid a ticket. The centers (inside the stone walls) have narrow streets, no parking and are hard to navigate.

Don't despair and don't give up on Tuscany. there is a good reason it's incredibly popular - the food and wine are fantastic, the scenery beautiful and the medieval hill towns are fun to wander around, plus some pretty nice churches and art. My point is that it's hard to go wrong no matter where you choose to stay. You won't see everything; some of your best memories will be of stuff you just stumbled across; some sites will be underwhelming relative to your expectations, and others better. I'm sorry I have no experience with Betolle, but it does seem to be right in the middle of where Roberto suggested you search. On google maps it's 20 minutes to Montepulciano, 1/2 hour to Sienna and under 1h 15 to Greve in Chianti, San Gimignano and Assisi (actual driving times might be a bit more, depending on traffic). If you find a hotel near there that appeals to you, then go for it.

Best,
Rachel

Thanks, Rachel.