Within 3 to 5 years, wife and I expect

I would look on the Florence /Rome line - Arezzo, Montecarchi, San Giovanni Vald'arno right down to Orvieto. 

I'm with you.I have been actively searching for an apartment in Lucca and am having a hard time finding what I want.I keep looking for alternatives, but nothing can match Lucca's uniqueness.I have the same criteria as you except the expat part (but not against it), I want to immerse myself in the Italian Culture.

I think if finding English-speakers is a priorty you are going to have a hard time beating Lucca unless you go to Florence.  Prato is significantly dominated by Chinese immigrants and Pistoia is, to me, an enchantingly typical small Tuscan city, but it I think it is thoroughly Italian.  One smaller Tuscan town that is a bit more "international" is the arts colony of Pietrasanta because it attracts an international co-hort of sculptors and sculptor-students.  If you are priced out of Lucca you might want to check it out, but it is not convenient to your plans to visit Rome a lot.   Cortona might work for you, likewise Perugia  -- but I don't think these places are cheap.  But another town with a fairly long history of English-speaking colonization is Gaeta, on the seaside south of Rome, partly because of the American naval presence there and also a little bit because the American artist Cy Twombly made a home there.  There is public transportation from Rome and you would not need a car living there.   Where is your own family from? 

ChiusiAlso look at Chiusi.  The old town is fascinating with wonderful Etruscan remains and the railway station at Chiusi-Chianciano has regular and fast trains to Florence, Rome, Bologna and siena.

Chiusi is a lovely, untouristy place but close enough to major English-speaker tourist draws like Cortona and Montepulciano that an English-speaker not yet fluent in Italian might easily find companions and activities to bridge the gap while making a transition.

I agree with robbiemarche and italmover! Consider also Orvieto which is just 20 min. from our Casale Prato delle Coccinelle. Orvieto is a beautiful town, lots of language and American Universities even though I agree with Marklt, I've been living abroad all my life and I prefer 'full immersion' into the culture. I would suggest my area however a car is essential.

I agree with the other persons who suggested Umbria, for example Paciano is a very small town with an international community (English, Australian), not far from the trasimeno lake. Chiusi  has a fast connection to Rome and Florence and is reachable in approximately 40 minutes.Ed Sheeran bought a casale in 2017 !Approximately the same time is needed to reach Perugia.This part of Umbria is lovely, but a car is essential.If you need more information about Paciano don't hesitate to contact me I can put you in contact with the English communityCiao,Milena 

Thank you all for the great comments and suggestions. My preference would be Umbria but the requirement for an English-speaking expat community is to help my wife transition (my Italian is quite good) and I am all too aware that a car is almost essential in Umbria, especially if one wishes to fully enjoy it!

come in Umbria, you will be well, there are many English and several Americanshttp://www.lifeinitaly.it/italiasegreta/regioni/umbria/Umbria.htmnear Todi, for examplehttp://www.todiscountry.com/todiscounty/todiscountry.htmhave some interesting offershttp://www.todiscountry.com/immo/sale.htm

I've was living in Rome when I got my first 'taste' of Umbria the southwest side which is very little discovered. I had a client who wanted to buy a 'rudere' to rebuild for a weekend escape. I didn't believe her when she had planned to drop the children off at school, drive to Umbria and visit several sites and actually return in time to fetch the children from school at 16:00! This area is just off the A1 Autostrada either with the Attigliano or Orvieto exits.  We'll to make a long story short, I've been here for about 13 years (5 constantly) and this area is completely forgotten by tourist guide books. You must consider we are on the border of Umbria, Lazio and Tuscany and we have the pleasure of discovering our similarities and differences in at least 15 minutes drive. We also have the advantage of having the Tevere in our panoramas, the WWF Oasis Lago di Alviano, Etruscan and Roman ruins, grotte, archeology, hundreds of hilltop villages, thermal baths, cities of art, the list is long...and not many iknow about it. Discover 'our side' of Umbria...the Valle del Tevere & Amerina Hills.

The biggest American community in Tuscany is naturally Florence. If you really want to live in Italy without a car outside a major city you will have to live right near a regional train station. That may not be the Italy you are looking for. Italy is not Brooklyn. Buses are sparse outside major areas. Countryside living in Italy is great because you can still be near a city and have all the perks of the countryside but you will need a car. Going for passeggiate in Florence is great but may get old real fast. Firenze is small. Come here with a plan A B C D and plan on improvising plan E when the former ones do not work out. I am not trying to scare anyone or pass on negativity- it is just the reality of living abroad. Hanging with fellow Americans can be fun but I am in my early thirties and would not have assimilated and learned the language if I was in an English speaking community. But it will help your wife and you during the period of culture shock all people naturally go through. You both will need others to lean locally on during that period. It will be harder not speaking the language. Italians are kind when you try to speak Italian -even badly.

An Englishman i met in Italy explained the process of culture shock -it may help you to understand it when going through it. Most people making large life changes go through it.

The first step is being in love with the new place and thinking it is better while comparing it to your former life. You will most likely temporarily withdraw from you friends and family back home as you brain adjusts to your new life.

Frustation will set in as many things will be different. Depression will set it. This is when strong interpersonal relations help. Embracing the local culture and not rejecting it at this point is crucial.

The third phase is when you can move between your two worlds with ease. You bloom again and get back on with living well.

This can take years to play out.

In bocca al lupo.

-Siena

Lots of helpful advice above but I will say that going on 10 years plus in Italy, in a town with some but not a lot of English speakers, I have never gotten depressed, so it's not inevitable.  I have had the usual run of bad experiences one can have anywhere over a ten-year period (things breaking, some plans not working out, health emergencies or sprained this or that, things where I needed a lawyer) but to the extent I compare my situation here with what I'd be experiencing in America, I think I've got plenty to be happy about. All that said, if one does get depressed, wherever one is, it's always good to remember it's not an unusual thing and nothing to blame oneself for. Who knows? I might get depressed tomorrow...Also regarding trains: There are many parts of Italy that are very well served by the train system while other parts are not, but in actually quite a lot of central and northern Italy, and coastal Italy, it is possible to live in a very small town or smallish city and have a short walk to a train station. And if one is more distant from the train station there is a frequent bus to the train and it is usually possible to develop a relationship with a taxi driver for those days when you need a ride to or from the station.  I've lived without owning a car for 10+ years and not found it a problem at all.  (Where I live it would be just as hard to find daily affordable parking for a car as it was when I lived in Brooklyn,and possibly worse!)For me, overall climate and food were some of the most important considerations for choosing a place to live. I like to wake up to sunshine as often as possible and I like to eat seafood and fresh fruit, so I looked along the coasts, where the train options are plentiful.  But if you want to keep Florence in the mix, and don't care about seafood, you should check out some train routes that would eliminate the need for a car.