Did you visit hill towns on your first visit? Siena area?

Tuscany is 9000 square miles, so it would be helpful to know which "other towns" you've already seen.

"Should we confine the trip to Tuscany or look into Umbria also?" You should read/research a bit about Umbria. There are some great sights, but we can't know whether you'd enjoy them more than the parts of Tuscany you haven't seen yet.

Are you heading somewhere else after Tuscany? Or a particular airport?

Our trip to Tuscany was about 10 years ago and we flew to Milan, went to Florence and also stayed in San Gimignano, Siena, Greve Montalcino and Lucca. We rented a car and visited some of the hill towns but since it was so long ago, we would be up for seeing them again. I am wondering if we should follow the same basic itinerary--we definitely plan to stay in Florence, Siena and Lucca but am open to suggestions. Sounds like we should stay in the Tuscany area as there is plenty to see there.

To each his/her own, but I'd spend some time in Umbria. Different scenery, new treasures to view, other wines to sample, etc.

Where are you flying into and out of?

I really liked Volterra, a hill town with a lot of history both Etruscan and Roman, and lots of alabaster shops. Worth a visit. ,

If you are definitely staying in Lucca, then you are very far west, and from there it is not easy to include Umbria.

However, from what you describe -- and I realize you can't recall the names of every town you saw -- it sounds like you have not visited the Chianti or much of the area south of Siena (Montepulciano, Pienza, Cortona, San Quirico d'Orcia), and some people consider this the most scenic wine country in Italy.

If you are basically thinking in terms of doing scenic driving, stopping in towns for their charm or shops rather than their art and history, then you might want to tour the Chianti and the val d'Orcia areas. Having an "itinerary" in this area sort of fights the feeling of freedom of exploration and discovery. It's just a fun area to drive around, popping into towns on a whim.

If you would like an itinerary that includes targeting towns with outstanding art (and fewer tourists), the towns of Umbria offer quite a lot of that as well as some lovely countryside, plus equally good (and perhaps better) food and wine.

By the way, if you can be happy re-visiting Lucca as afternoon out of Florence, rather than spending nights there, you will have an easier time creating an itinerary where you see new areas of Tuscany, and some of the more famously scenic areas of Tuscany, and perhaps include some of Umbria.

In Tuscany there are many beautiful areas that not even Tuscan people knows and that you will hardly find on travel guides. It depends,as always, on what you are asking to your travel. Relax? Art? Wild landscapes while driving? I will tell you what I would do in two weeks in Tuscany: I would take aim at visit Tuscany not in a rush. Driving and stopping every time that the road suggests me to do it, just to admire a little old church or a castle's ruins, or to stop in a small shop of 'alimentari' to have some bread (Tuscan bread!) and wine (Tuscan wine!). I would avoid to stay in the big cities, because in May the countryside is a rainbow of colors with flowers of every kind. I just would fix a base and then move for daily trips to Florence, Lucca, Pistoia, Pisa.
So I would stay in Mugello which is just 20 km away from Florence, but instead than being crowded with tourists it is crowded with animals. Here you can stroll among trees which are not less 'Tuscany' then 'Duomo', if you know what I mean.
If you want to experience Mugello, I would definitely suggest Borgo San Lorenzo and if you are looking for a place to stay I think you should have a look on this. www.monsignordellacasa.com

You know, even if you are going to visit twice the same place, if you visit it in a different period of the year you will find all different, because of landscape's seasonal changing. Perhaps it won't be so obvious if you stay inside a city, but if you mean to drive in the countryside you are going to discover a great nature.
You wrote you have already been in San Gimignano and Siena, but I think Chianti is worth to have even a second visit in the less known and most true-to-life of its area.
Castellina in Chianti, Radda in Chianti, Gaiole in Chianti are beautiful villages and you will hardly find tourists here.
As a place to stay try www.borgopietrafitta.com in the Gallo Nero Country

I am beginning to collect some great ideas! We did tour the Chianti area when we were there ten years ago and I agree that it would be a wonderful area to focus on more this trip. Perhaps it would be good for us to check out some place to stay in this region and then we can have a combination of countryside and city.
Our goals for the vacation are to see the beautiful scenery, experience great food, wine, as well as the culture and history. We do like to explore and when I say itinerary, I am mostly thinking of regions and where to stay....after that, we explore.
So maybe, we should stay a few days in Florence, Siena, for the cities and then stay in some countryside place in Chianti and then figure out whether we should go to Lucca or not and what else might be fun and interesting. I will check out the accomodation recommendations given and try to firm up some more ideas.

drkathej - did you say where you are flying into and out of?

that info would help us with making suggestions about an itinerary.

also i note that you have 14 days or so - in which case you probably won't want to have more than 3 bases, or at most 4.

We thought that we would fly to and from Milan (unless something else would be more convenient). We will be coming from Boston.

Pisa, Florence or Rome would be closer than Milan. Depending on what you finally decide itinerary-wise, it might make sense to fly into, say, Pisa and out of Rome. Or vice-versa.

Unless you want to visit Milan on this trip....?

If you think you might want to visit Lucca, you should add a day to your stay in Florence so you can visit Lucca. Once you get to Siena or in the Chianti, it gets a lot more time consuming to make a visit to Lucca.

You really don't "lose" much by adding a day to Florence without being sure how you are going to spend it. If once you are there you think: "Let's see something new instead of Lucca!" you can take the train to Bologna, or take the bus up to Fiesole (see the Roman ruins and have a walk where Michaelangeo walked), you can see the Museum of San Marco in Florence itself (look it up online) or a zillion other museums some of them quite odd ball (shoe museums, medical anatomy museums). Take a cooking class.

Or, if you really miss Lucca, you have the time to go to Lucca. Bike around the walls.

We thought that we would fly to and from Milan (unless something else would be more convenient). We will be coming from Boston.>>

definitely think about doing an open-jaw flight into one place and out of another so you don't have to retrace your steps - you need to look for the "multi- trip" or multi-city button on the airline website, and it shouldn't work out any more expensive than a round trip.

so, for example. if you wanted to see something of Tuscany and Umbria, you could fly into Rome, get the train to Orvieto, spend a couple of nights there, and then collect a rental car, using it to tour and work gradually north, until you get to Siena, where you could return the car, then get the bus or train to Florence [where you definitely don't want a car] ,and then the train to Pisa airport to fly home.

oops, sorry I misread your first post.

Scrub Siena.

there are of course hundreds of permutations, but you get the idea.

Have you visited the Ligurian coast? We liked Santa Margherita Ligure a lot.

It's really helpful to know that other airports are closer to our destinations and I will look into that. The choices are so many so I am feeling a bit overwhelmed at the moment. I plan to do a bit of reading, try to narrow things down and go from there. Basically, I need to identify the places we will stay and then we can do exploring from our base spots. Our trip can change quite a bit if we decide to stay in Tuscany versus venture into Umbria. I am open to suggestions regarding itineraries--knonw we definitely want to include Florence, Siena, Chianti area and Arezzo.

If you know you definitely want to include Florence, Siena, Chianti area and Arezzo, that is definitely a full week. Flying into Florence, getting over your jet lag, and then renting a cary to enjoy a spot in the Chianti hills for a few days of whimsical exploring can be a lot of fun.

After that, it could be interesting to make a foray into Umbria, but then I would want to fly out of Rome, I think. But I think what I would really prefer is the area around Pitigliano, Soriano nel Cimino, Saturnia, and other parts of southwestern Tuscany. This is a much less touristed part of Tuscany with quite fascinating features. You might enjoy seeing this other aspect of Tuscany, which feels more off the beaten track and is less conscious of tourism.

While it is not a huge headache to use a car to visit Arezzo, you can visit Arezzo by train from Florence if you prefer. If you decide to go by car, spend some time with a good map identifying your path into the small city and where you will find public parking lots. Because Arezzo is an important regional commercial center, it has plenty of buzzy traffic at its edges, so it's not like just popping into one of the sleepy villages. It helps to have a plan.

By the way, I sympathize with this "overwhelmed" feeling of planning a trip to Tuscany, but this is partly the fault of guidebooks and other misleading advice people get. Most of Tuscany is really very very lovely and full of general interest. The mistake, I think, is to imagine one needs to fuss about where to "base". I see all these posts about "Which hilltown????? HELP!!!" Honestly, it scarcely matters.

It really can be worthwhile to make time to see a specific great artwork (as in Arezzo) or a specific great piazza (again, as in Arezzo!) or abbey or winery. It can help to give some thought to what you want to emphasize for your trip -- seeing more of Italy? Or relaxing more in Italy? Spending more time inside towns, seeing churches or shopping? Or spending more time in your car, enjoying scenic driving? Seeing more of the famous places? Or deliberately seeking out something off the beaten track?

But I wouldn't agonize about getting more specific than that in Tuscany. It's like a many-roomed mansion with miles of gardens, stuffed with treasures and curiosities at every turn. It's hard to go "wrong."

Thank you for all of the feedback. I am doing some research now to determine if we should head to the Lucca area after Florence and Chianti or head to the south west as suggested by golden autumn. I will then pose some more questions!
We would like to stay in a combination of city and country sites. The reason we like a city is so that there are great restaurant choices without the need to drive. We love wine, food, the ambience and just driving around to explore. It's not that we need to do anything in particular, just enjoy it all! I agree that anywhere is good as a base, but then again we do have to pick somewhere! So, as of now, we thought Florence, San Gimigano, Siena, somewhere in the Chianti area and then either the southwest area or the Lucca area. Any thoughts are appreciated--but I will pose another question when I get some of the specifics down.