Another vote for Umbria, and Assisi - but if possible out of season, and outside the middle of the day...

If you're looking for a lovely, calm, atmospheric place to stay in the old town, at reasonable prices, try:

http://www.i-escape.com/sancrispinoresidence.php

I only stayed 2 nights but loved it. The girl on reception (Isabella) was as kind and helpful as described.

Natalia, thanks for the vote of confidence. I still might post something, however, mine will have to be the "traveling with toddler" version which will make it much more interesting (albeit amusing) than others. And people thought traveling to Europe alone can be difficult - try it with a baby and then a toddler - plus stroller! It is interesting beyond compare. :-) Anyway, I always manage to have a wonderful time and my little one speaks and understands Italian now too, so I don't mind taking her along (and as an added plus, I get incredible exercise lifting and hoisting!)

I am returning again in March and April, but this time plan to stay in just Rome and Naples areas. I would like to try and see Orvieto this time around - maybe as a daytrip from Roma (I would like to see its famous black-and-white duomo/church, I have heard it is just magnificent).

Natalia - I truly enjoyed your report. If you are still checking the board, I have a question for you. I am planning a trip for myself and my mother (who is 67). She is in good health but has trouble walking UPHILL. She becomes very winded and panicky. Is Umbria out of the question? Thanks so much - Cathryn

Cathryn, I hope I gave you some information you can use. One of our party had trouble walking uphill too, but he went slowly and didn't mind
sitting at a cafe and taking in the ambiance while the rest of us walked around. Some of the towns had busses, such as Montepulciano and some had parking lots you could drive up to.
In Spoleto we drove up to a square and dropped him off, then parked and walked back up.
If you are training it, it might be more of a problem.
If you would like, just list some of the towns you would like to visit and either I or someone else here can help you with the logistics of walking there.
Some of the towns are flat, such as Pienza and Siena is relatively flat.
Keep in touch and I would like to help you decide. Thanks for the nice words.

Natalie - you may be getting in for more than you bargained! Here is a bit of relevant background -

In May my mother and I went to Britain. Lovely two week trip - however - as I was planning it seemed to move along in a circuit so instead of choosing bases & working from there we moved every night. By the beginning of the second week - exhaustion!

So now it?s Italy! Once you start reading guide books - everything sounds great! So I am trying to figure out what it is I REALLY want to see - what drew me to Italy. hmmmm.

Ride along the Grand Canal (at dusk )
See an Opera
Sit on a terrace overlooking the Tuscany countryside drinking wine and eating olives
Explore a classically Italian Garden
Shop for pottery in Gubbio
See something of ANCIENT (not Renaissance) Rome, possibly daytrip to Pompeii (on train/bus)
Visit ONE of the many magnificent art museums, the Uffizi or the Borghese

RELAX, stroll, meander, take a break and enjoy!

We will be flying Continental (husband's frequent flyer miles) and can easily come into and/or out of Milan and Rome. Venice or Florence requires going thru Amsterdam and takes so much longer that it isn't worth it. Could also do this itinerary in reverse order.

I do want to do a large part of the trip by train. - but would rent a car for 2/4 days in the country (NO CITY DRIVING PLEASE!)

Fly into Milan - train to Venice
2 nights Venice - Westin with points
3 nights Florence - Westin with points
2 nights Siena - or should we stay all four south of Siena and day trip?
2 nights Umbria
4 nights Rome - Hilton with points

Considered taking one night out of Rome, adding a nite in Milan or Verona so that we would be refreshed when reaching Venice on the next morning.
I had hoped to go this May but we may not be able to pull that off and so it may be September.

Any words of advice?

Hi Cathryn,

Very nice trip. I would spend ony one night in Siena (or even do it as a day trip from Florence) and add it to Venice.

Are you planning on picking up a car in Florence and then driving through Tuscany and Umbria on your way to Rome?

Oh Natalia - here I have been thinking how pretty your name is and I spelled it wrong - I am sorry.

Thanks Ira - I admit it is kinda scary to post right now - some people can be HARSH! Would you go all the Milan to Venice the first day (we would be there by about 2:00 based on train schedule) or stop on the way?

Yes - Planning to pick up car in Florence (southside hopefully) drive thru the area and return it outside Rome. If I can I might even return it somewhere like Perugia or Orvieto and train to Rome from there.

I want to experience the loveliness of this area but am not eager to drive after my GB experience. It was stressful for me and my mother - I don't think the freedom of it outweighed the added tension! Of course we were driving on the left out of London, thru Bath and thru a TON of 1 lane roads in Scotland. And I haven't traveled via train/bus previously. So what the heck do I know - and that's the rub you don't REALLY know till you go.

If I could have just the thing I wanted (it is all about me, just ask my husband) - it would be an apartment or room just outside of Florence, easily accessible to public transport with a pretty view, terrace and lots of light! Then I would save my Westin points (or use them to stay at the Gritti in Venice!) and spend my Florence/Tuscany time there making day trips. I have been looking and looking at lots of sights recommended here) but can't seem to find the right place. If anyone knows . . . . Thanks to all!

Cathryn, please dont be afraid to post here there are so many people anxious and willing to help you.
It might be best to start your own thread to get the most answers and help, but I like your idea of renting a place for a base.
I have rented villas alot and find they are so much easier if you have someone who tires easily or may want a day to rest, etc.
It is so nice to come home to a villa and sip wine or have a leisurely breakfast on your own terms in a lovely place.
I would suggest, flying into Milano, see the sites and overnight there, take the train to Venice (use your points) and stay there about 2-3 nights, then go to your rental place (be sure it is near a main road) and take day trips into Florence and in Tuscany, then end up in Rome and fly out of there.
I think it is really easy to drive if you do it leisurely and give yourself plenty of time to get somewhere and give yourself permission to change plans or linger longer someplace.

In fact you whole mindset will give you a better trip, if you dont' try to do too much and get into the Italian rhythm of life. Take things easy, admit to yourself that you wont see everything, be willing to change plans, plan on seeing whatever you have missed on your next trip. Your mother might enjoy this attitude too, rushing just makes everyone tense and pressured.
I speak from experience, believe me.

So.....write a question starting a thread with a main question in the title and we will all help!

Thanks Natalia - I wanted to reply in Italian but am too chicken (I plan on an conversational Italian course in January!)

I have read so many posts and have a plan kind of put together - I will make the giant leap and start my own thread soon. Thanks for the encouragement!

Mu husband & I are just in the beginning phase of planning a trip to Umbria. What time of year do you reccommend traveling to this area?
Thank you j

I haven't been there in the winter but it might be nice then. I was there in Sept and really liked that time of year, not very crowded and warm, hot and cool days and cool nights. In the Spring there is alot to do also, I have been in that area at that time too.

What are some of your interests?

Just topping my old trip report for an old friend.