...in Chiusi, yes, and in Arezzo, where the crowds are concentrating on just one church (the one with the Piero della Francesca fresoes), and you have the (wonderful) rest of town for yourself.

...frescoes, not fresoes, just in case anybody else is suffering from the heat and didn't get what I wanted to say :)

I prefer freschi myself. And I agree about Arezzo being wonderful.

And I would like some fresca air. How is it where you are? I think I felt a breeze a few days ago.

louistraveler5,

if you're lurking and haven't bought your air tickets yet, I'm increasingly thinking that maybe the best itinerary for you is to fly into either Rome or Florence (or even Bologna or Pisa) and take a train directly to Cortona. All the train trips are about 3 hours.

Spend 2 nights in Cortona. Then take the train either to Chiusi or Arezzo and pick up a rental car to drive into scenic Tuscany. Which town you pick partly depends on your next base in Tuscany.

Go to a base in rural Tucany of your choosing for the next 2 or 3 nights.

Use the car to drive to le Cinque Terre, and stay in a hotel with free parking. Stay in le CInque Terre for 2 or 3 nights, depending on how long you chose for rural Tuscany.

Drive to the Florence airport, drop off the car, take a taxi to a hotel in Florence. Spend your last nights in Florence and fly out of Florence.

If you've decided to see Venice instead of spending time in Florence, I recommend flying into Venice, spending 3 nights there, picking up a car and heading to rural Tuscany, near Chianti or south of Siena. See Cortona as part of your Tuscan stay, as a day trip, Use the car to drive to le Cinque Terre. If you are lucky, you can find a flight out of Pisa or Genoa that doesn't leave until late morning, so keep the car and drive yourself to the airport. If you have to spend your last night in Pisa, Genova, Florence or Milan, might as well get rid of the car on your way to le Cinque Terre. Drop off the car in La Spezia.

Since you are traveling in October, I highly recommend that you not book your le Cinque Terre stay -- or only book in le Cinque Terre hotels with a 24-hour cancellation policy. It is really not worth your while to be in le Cinque Terre if it is raining. Have a back up plan. There is plenty to Tuscany to fill up your time until it stops raining in le Cinque Terre (if it does) and you won't have trouble booking last minute in either area in October.

Ok, since we don't hear back from louistraveler, we can as well continue planning her trip without her input ;)
zeppole, one objection and one amendment. The objection first: we still don't know about louistraveler's level of interest in Renaissance painting and the like, i.e. of her interest in Florence. So you're in danger of making the same mistake that you've been criticizing us for - deciding what has to be good for her. If she wants to spend six or seven days in Florence, there's not enough time for your (otherwise certainly excellent) plan. And that's what I was thinking, in the light of louistraveler's Paris experience - I thought six days Florence, 2 to 4 days Cinque Terre, depending on HER preferences... which leaves another two to four days for rural Tuscany, which isn't that much, hence my thought about skipping Cortona... but ok, let's suppose Cortona is a must. So here comes, no. 2, my amendment to your plan: louistraveler, if you're generally fine with zeppole's itinerary, my suggestion is not to STAY in Cortona. It's in a generally very untouristy part of Tuscany, and the only touristy enclave there. Just a few kilometres away, there's a quite similar hilltown, Castiglion Fiorentino. It doesn't have a major sight like Cortona's S. Maria al Calcinaio (outside the walls, and Cortona's single claim to architectural greatness IMHO), but there's little difference to Cortona inside the walls, just that nobody ever visits Castiglion Fiorentino, so it's still the perfectly functioning Italian small town that also Cortona must have been before growing famous. In the surroundings of Castiglion Fiorentino, if you'd rather not stay in town, there are quite many excellent agriturismi (if you're interested, I can look up the address of the one where I've been immensely enjoying my stay, but only if you're interested - with the current heat, I try to move as rarely as possible).
Castiglion Fiorentino (or its surroundings) would provide you with a definitely non-touristy setting, and Cortona is just 12 kilometres from there: 15 minutes by car at the most, so you can daytrip there as often as you want, without STAYING in non-functioning towns and tourism-afflicted parts of Tuscany all the time.

I don't assume louistraveler5 isn't coming back. The trip isn't October 2011! -- !!!! Possibly he or she has duties that make it impossible to hang on every word posted on Fodor's.

I am sorry if any of my posts implied that louistraveler5 shouldn't jettison all our ideas in favor of doing PRECISELY what the travelers want to do -- with the freedom to change their minds right up until the last minute -- even in the middle of the traveling, which in October would be a cinch.

Unfortunately, air tickets must be bought at some point, with the entry and exit point fixed. FORTUNATELY, Florence and Cortona are pretty much dead center in Italy, surrounded by international airport connections. So even after tickets are bought, nothing has to be set in stone -- with the possible exception of flying in or out of Venice.

louistravel5....Take an Ambien on the plane! Sleeping 6-8 hours on the plane makes a world of difference upon landing and time adjustment. I am not a drug pusher. It works for my husband and myself.
Tina

I second tinabina's suggestion and I HATE to take pills but I take a valium on transatlantic flights, not because of jet lag (although sleep certainly helps with that) but because I am terrified of flying.

Also, as soon as the plane has left the runway, I set my watch to European time. And we never, ever, ever allow ourselves to sleep when we arrive. We did that on our first trip to Europe and we had jet lag for almost the entire trip.

Hi everyone...I'm back! Wow...I am surprised this morning to find that my post has 26 replies! I checked before I left work yesterday and only had 5.

Zeppole: You stated in a reply- "By the way, I suspect the only reason Louistraveler5 put "zeppole" in her subject line is because I live near le Cinque Terre". I did not know where you live and I put those names in the title of my post because I saw many responses on the Italy forum by all that I named. I wanted an array of ideas for my trip.

My trip isn't until 2011. My birthday is Oct 4 so I am planning on departing Thursday September 30 and flying home Monday October 11 which gives us exactly 10 days in Italy.

As for the jetlag...we are planning to take an Advil PM on the flight there and then for the first night or two if needed. I'm not going through what I did in Paris again. I've taken an Advil PM before and it does not me groggy. Tinabina
put it best..."I'm not a drug pusher".

I don't really know what to say about all the replies...so many people ask how much I'm interested in art and architecture. Well, I like to look at art and marvel at architecture but I don't LOVE it. I may not LOVE it but I appreciate it. I'm simply interested in traveling and seeing new places and I've always wanted to go to Italy. This seems to be coming out wrong...I don't want everyone to get the wrong idea that I'm just going "to go". I guess I don't have a focal point of interest. I like all kinds of things and love seeing new things while traveling. One thing I can say that I do NOT like is wine and I know, I know, I'm going to Italy and I don't drink wine. Not to say that everyone that goes to Italy is going to drink wine but one does think of it while traveling the Tuscan countryside. I have a feeling none of this is coming out right.

I will just conclude with: I've always wanted to travel to Italy; I've always wanted to experience/see Tuscany; I want to Florence to be my "city" to see this first time in Italy; my main goal of my original post was to get an idea of which Tuscan hilltowns plus Florence and Cinque Terre I could fit into 10 days and to get an idea of which Tuscan hilltowns a first-timer to Italy should see.

Thanks for all the replies and I will continue to research which Tuscan hilltowns I would like to incorporate during my stay. Next year when I am closer to my trip I can post again about a set itinerary. Thanks again!

Your welcome -- and please don't apologize for your interests in being visiting Italy which may not conform to other people's. It is refreshing to read that you understand yourself and are crafting an itinerary to suit your own interests.

Wine is not at all important in Liguria, which every year lands at the bottom of Italy's regions when it comes to wine production. Drinking the wine in Liguria will not improve your liking of wine, believe me! Also, many people go to Tuscan wine country and never develop any interest or liking for the wines there. They go to see the beautiful scenery and the towns. One of the reasons Tuscany has become so popular is because many travelers wearied of being in museums on vacation. They enjoyed looking at beautiful things -- and they are all over Italy -- even is some small churches in le Cinque Terre -- but they did not want to be spending all their time studying art.

While you are studying Tuscan hilltowns, study some Italian too! You can find free programs on the web! :-)

louistraveler, before you leave for your hilltown research sabbatical, one more thought. The question is not which hilltowns you "must", or should, or ought to see as a first timer to Italy. The question is which ones appeal to you; and which ones fit into your itinerary. This thread is outlining two ways of dealing with it: either go to the well-known towns where typically most first-timers go, and meet them there; or since you already have two major tourist destinations, Florence and Cinque Terre (plus Cortona, if we stick to what we've been discussing lately), try to avoid, for the smaller rest of your trip, meeting other travelers, and go to hilltowns where typically no first-timer ever goes. Since I'm advocating the latter, and since it's not guaranteed that we'll meet again when you come back to Fodor's next spring or whenever you're done with your research, I'm adding a few non-touristy suggestions (other than Castiglion Fiorentino, Chiusi and Arezzo - see above). If it turns out that you have little time or energy to travel back and forth (Cortona/Arezzo being in the opposite direction from Florence, of course, than the Cinque Terre), there are some interesting options that involve far less driving; of course, you could also use them in addition to Cortona-Arezzo. First of all, Certaldo south of Florence, and nearby Castelfiorentino (similar name as Castiglion Fiorentino, but a totally different part of Tuscany). Certaldo, above all, is absolutely wonderful, and both towns get few if any tourists. In the same region, if you have the nerve to go past S. Gimignano without visiting (which nobody ever has!), you could proceed to Colle di Val d'Elsa, with no spectacular sights and once more, with plenty of down-to-earth (or rather, down-to-hill) flair. Closer to the Cinque Terre, there's the mountain town of Barga, a spectacularly steep medieval town with an impressive little cathedral that is among Tuscany's oldest churches; and Carrara, rather a small city than a town, with an absolutely wonderful late Romanesque cathedral, and plenty of unspoiled atmosphere - a model of a well-functioning Italian town.
As for the well-traveled hilltowns, you've already got all possible advice on this thread. Of course, you could also do one more combination of touristy and non-touristy (like Castiglion Fiorentino-Cortona-Arezzo-Chiusi, that is) and visit Certaldo, Castelfiorentino and S. Gimignano. The comparison between S. Gimignano and Certaldo is striking, and a lesson in how arbitrarily the tourism industry is choosing their "must-see" places. Both towns have those medieval tower houses. In S. Gimignano, they're built in stone; in Certaldo, in brick. Otherwise, very little difference. Just that S. Gimignano is so overrun that you'd be hard-pressed to find a "real" person there (i.e. somebody living there without being a waiter, or a hotelier), while Certaldo is a self-contained place with some (small-scale) industry in the surrounding plain, where people are finding work, and the town is definitely functioning. And both towns have frescoes by Benozzo Gozzoli. (Ok, those in S. Gimignano are far greater, but they're not the reason why this is such a landmark on the tourist map of Italy - of all those throngs of visitors, perhaps 2 percent bother to visit S. Gimignano's greatest single sight.)
Finally, to the Cortona-Arezzo region, let me add Sansepolcro - not a hilltown but in the plain, and another absolutely lovely example of an unspoiled small town.

louistravel5- I tried the AdvilPM on our way to London 5years ago..not strong enough for "knock you out sleep like a baby on a plane" kind of rest. See your family doctor and just get a prescription for 5 or 6 pills, of an Ambien type med. Each of you take one on the plane, take one the first night in Italy and then perhaps on the plane ride home. It will make the vacation a million times better if you can hit the ground running, rather than fall down face first on the ground.
Tina

Okay off the topic of "Drugs".

I just returned from Italy, last week, and hope to organize my thoughts into a trip report very soon.
Meanwhile,
It sounds like you may be a bit similiar to myself, as far as travel interest.

We did go to Tuscany! (from Rome:driving a car.

I loved the whole driving through the countryside and seeing amazing town after town clinging to the tip top of hillsides. Amazing.

We went to-
Orvieto(day)...then onto Perugia(evening/spent the night)
I preferred Perugia.
Siena(day)...San Gimingnano was<FAVORITE>just my opinion. Felt like what I had imagined Tuscany would be like.(evening/night).
Pisa(morning) and Lucca(day-but it was Sunday afternoon and the place was a ghost town)
Florence(evening/2 nts.)

It was our first trip to Italy. We also went onto Venice for 2nts.

I loved it all. San Gimingano was my favorite hilltown/hotel and meal...so I am biased.

You will most likely find all of it very unique and magical.

Just my 2cents.
Tina

PS..I don't drink. Didn't affect my love of Italy or Tuscany, even a smidge. I did however develop a semi-serious gelato habit.

tinabina:

I would love to read your trip report and I look forward to you posting it!

Where did you stay in Perugia?
Where did you stay in San Gimingano?
Where did you stay in Florence?

Your trip sounds like the perfect mix for a first trip to Italy!

louistraveler:

Hi again:

Perugia:
La Rosetta Hotel.
Quaint=no shower, just bath with wand shower.
Neat location within the walls-on a piazza-included breakfast.

San Gimingnano:
Leon Blanca.
Perfect hotel, on the main piazza..terrace overlooking the Tuscan hillside...shuttered windows to lean out of and wave to "tourists". Just lovely. Nice breakfast..great included cappucinos. Dinner with excellent view. Check trip report for the name of Restaurant, later.

Florence: Bad choice for hotel on my part-too far from everything. Won't bother with a name.

Rome:
Medditerrano: Nice enough, good location for train/termini, 15 minute walk to Colosseum, good included breakfast. And terrific "make it yourself espresso/cappucino machine". I had 3 every morning. Zing.

Venice:
Hilton Molino Stucky: Just because we wanted the "american" style hotel at the end of our trip when we were tired and I needed a big fat bubble bath. Nice hotel, a bit far from main Venice, but quiet and comfortable and had shuttle boat to San Marco from the hotel every 20 minutes. Only place where breakfast wasn't included.

I will get on the ball and write the trip report within the next few days.

Tina

I'm also planning a trip to Italy for June 2011 and would be interested in reading adventureseeker's 19 days in Italy, but I'm having trouble finding the old posting. Just signed up and am learning so much from everyone.

adventureseeker's trip report:

http://www.fodors.com/community/euro...t-to-italy.cfm

louistraveler5, as you're now asking about Perugia, it seems you're not locked into CT/Florence/Cortona. Good. I'd spend a few months reading guidebooks, watching travel shows, DVDs (Netflix has a few) or online videos, peruse the coffeetable/photo books at the bookstore or library, etc. You may decide on other destinations than your original plan.

Where are you flying from? DFW? I think you should figure out your flight options before you decide too much. Yes, there are lots of airports throughout Italy, but reaching one in Tuscany may require waiting for hours (or changing airports) in Frankfurt or London or wherever. I'd look for flights/connections that get you to Italy fastest. Ten days is not a lot of time.

also backing up tinabina's recommendation for a strong pill like ambien. I just returned from italy 2 weeks ago and am still readjusting. The sleep/time derangement was very difficult. Next time, I am definitely taking meds. I can't overstate how important this is.

Louistraveler5, it's Adventureseeker here! I'm back...I was feeling a bit nostalgic and needing a "Italy" fix or perhaps just the simple thought of embarking on a new adventure, so signed in to the boards and was greeted with your lovely post!

I have been away from the boards for some time (as to be productive and not while away my days dreaming about travel! Which all of us travelers can easily do 24/7!). I hope you had a wonderful and memorable trip to Italia.

WOW!! Thank you all so very much for your kind and generous compliments on my trip report from 5 years ago. It means more to me than you know. I love sharing every detail with anyone who can gain from it, those who are "hungry" for it and especially those who don't get bored or glazed over from hearing/reading it!

Grazie mille, from the bottom of my heart!
Adventureseeker