My DH & are planning our first trip to Italy for October 2011 which will be during my 30th birthday. Our first and only trip to Europe was to Paris in October 2008. Our main focus will be Florence, Tuscan hilltowns and Cinque Terre. Our trip will be for 10 days excluding travel. I have posted, recently, on this board about which Tuscan hilltowns to visit.

Zeppole-you responded to that post. I took all the replies to that post into consideration but I still need help putting the puzzle together. I have not decided which Tuscan hilltowns to put on our itinerary so I would like some sample itineraries from you Fodorites. I know the trip will ultimately be of our choosing but I would like to know how you would put it together such as:

1) How many days in each place: Florence, Tuscan hilltowns & Cinque Terre?
*Sidenote: we don't mind renting a car, we know it will be a necessity for traveling to multiple Tuscan hilltowns.

Adventureseeker: If you read this post, a note to you...I absolutely LOVED your trip report of your 19 days in Italy! I have actually read it more than once! It is because of you that I want to go to Cinque Terre. I, as well as you, love the planning aspect of a trip.

A couple more things:
1) One Tuscan hilltown I would enjoy seeing is Cortona. I don't have to see it this first trip nor do I have to base my itinerary around seeing this one town but if someone had an idea to incorporate this town and others nearby, I would take that itinerary into consideration. It may not be everyone's taste but I do like the movie "Under the Tuscan Sun" and I don't have any notions that the town will be like a "movie".

2) An inside look: Our trip to Paris was very, for a lack of a better word, rushed. We went for one week, 6 days total, excluding travel. We were NOT overwhelmed by the language barrier or euros but the time change did affect us significantly. We flew from TX so the time difference was 7 hours ahead in Paris. We barely slept a wink on the flight over so we were off to a bad start and we did the ultimate no-no and took a nap! We slept for a couple of hours then went to get something to eat. We just felt so disoriented and it was so hard to adjust because in the mid-afternoon it was breakfast time at home. We stayed in a flat for the week and we wouldn't go to bed until almost 2am and even then it was hard to fall asleep! We would set the alarm between 7-8am but always fall back asleep until 10am. We had the "main sights" that a typical first time visitor has on their list and we weren't intentionally trying to rush from sight to sight. That is not what I want my traveling experiences to be about. With the time difference affecting us, it is what our trip turned into. I know Paris can not be seen in only one trip or even in multiple trips. I do feel I owe Paris a second chance someday. On my trips, I want to savor moments, take strolls, see some sights and experience being in that place. My dream in life is to travel the world, I have so many places I would love to see. I thought of this first trip to Italy and considered Florence, Rome and Venice. I've also considered Florence, Cinque Terre and Venice. I do worry that if we chose Rome or Venice it would Paris all over again. A big city and rushing to sights. I don't want that to happen...how do you avoid this? Ultimately it wasn't my fear of Rome or Venice turning into a rush as why I am not going there for my first time to Italy. I feel a pull towards Tuscany and I must see the five villages of CT clinging the cliff and spilling into the sea. How many of you out there think I should consider Cinque Terre, Florence and Venice? Remember, with 10 days our time is precious! How do you savor the moments and not rush from sight to sight? How do you deal with the time change?

I know this long-winded but I feel it gives in some insight as to who I am and how I want to travel and it will help you Fodorites to create a sample itinerary. Thanks in advance to any and all replies!

I'm no expert on Italy (ask zeppole!), but I'm thinking that maybe you should start with Tuscany or Cinque Terre so you can recover from jetlag in an area where it would be very laid back. We're planning a trip which also includes Tuscany right too and are looking at it as just go with the flow (if we can figure out which area to use as a base that is). Sorry I can't help you with an itinerary.

My best advice to you is to have a MAX of 3 destinations in your short time. And, the flight connections may well dictate your sequence. The ideal scenario will be to fly into Florence and home from Pisa--OR VICE VERSA. I would start there to see the feasibility from your home location.

Given good connections, I would start in Florence and do this:
Florence---3 nites
Get car--to Tuscany---4 nites
Drive to La Spezia--drop car---train to CT base
Train to pisa for flight deparure
The location in Tuscany is always key to me. Cortona is not your best location, and there are better hill towns to see. Do not let the movie spoil your judgment. I would base either near Siena or south of there---Pienza or San Quirico. I assume you have seen my list of hotels and rental properties in Tuscany.

louistraveller5,
This may help http://www.slowtrav.com/italy/tuscany/hs_planning.htm

Henry

Hi louistraveler5!

I'll bet bob is just as surprised as I am to be asked for help in the same post. We have completely different ideas about happy Italian travel, and usually disagree -- and I'm afraid this time won't be an exception.

To me, it is good that Paris taught you so much about what is and isn't a successful trip for you. Use that information to pace how to see EXACTLY the things you want to see most. There is a limit to how much you can see in 10 days, as you know, but at least know your priorities.

To me it is a given that you want to see Cortona -- a fantastic historic town with great artworks and personal meaning for you -- plus other parts of scenic Tuscany, and of course le Cinque Terre.

That is certainly doable in 10 days, even if you walk!

So the question is: What else do you feel you would be happiest to see and do?

If the answer is strolling Venice and taking in its artworks, either fly in or out of Venice. If you fly in, rent a car after you've seen Venice and head for an area near Cortona or in the hills above Cortona itself. (There are plenty of other beautiful places within an hour's drive.) If you would like to end your trip in Venice, it makes sense to sandwich the Tuscan portion of your trip in the middle, and use the car you rent to see scenic Tuscany to drive to Venice, and drop it off there.

If Venice sounds like a tourist rush of too many things, and the Renaissance is what thrills you, and you can't live without seeing all the paintings and sculptures and church art of Florence, head to Florence! Great if you can fly into there or Pisa, If you want to see Florence as your major city, it really doesn't matter which order you take your trip. But it does seem to me that since you had such a bad experience with jet lag in Paris, that maybe your first stop should be le Cinque Terre or a Tuscan farm near Cortona. You can take a train to Cortona from either Pisa or Florence or Rome -- so that's another possible fisrt stop.

It sounds to me like Rome would be the least satisfying city given your other priorities -- and be assured that are many sights of antiquity and papal extravaganza all over Tuscany -- so you will see that even if you skip Rome.

Last but not least -- if you only go to Cortona, scenic Tuscany and le Cinque Terre for 10 days, you can be astonished at what a rich trip you can have, with Roman and Etruscan ruins you can track down (even near le Cinque Terre), jaw dropping architecture and painting, edcuational museums -- and it is not hard to take a day trip into Florence from Cortona if you want more.

So take the trip to Italy you want to take -- your own private Italy. Yes, it would "be easier' or make "more sense" if you walked a certain tourist track -- but this is YOUR trip. If you decide between now and October you just MUST go to Rome to throw coins in the fountain -- hey, it's only 90 minutes by train from Florence. WHo cares if other people thing you'd be "wasting your time."

Hope that helps to make a start!

This may or may not help you, but with our ten nights in Italy next June we have chosen to spend all ten in an Umbrian town (Spello) and focus on a narrrower slice of Italy. This is an apporach to travel that has worked for us in the past in other countries and requires an aknowledgement that we will be not be seeing everythinng there is too see, but we will see and experience this area deeper than if we had planned 3 or 4 nights there. We'll just have to add Bologna and Venice to the list for next time. You might think about interjecting a bit of that thinking into your plan. How about a 5/5 split between Tuscany and CT and shelve the rest?

Anyhow, there are far more experienced Italy travelers posting here than myself, but when I saw your title, I thought I would share what we are doing with our 10 nights in Italy.

Have a great trip.

I'm not adventureseeker, I'm not Bob, and I'm not zeppole - sorry that I'm chiming in nonetheless. First of all, what Paris has taught you is the best of all possible starts. Period. Second, you are set on two tourist-red-alert destinations, Florence and Cinque Terre. There's nothing wrong with that, if you're just prepared that you're not going to be sharing the café on main square with a group of senior locals. But I strongly advise to postpone Cortona to your next trip to Tuscany, and to choose some tourist-free hilltowns for the middle portion of your trip; otherwise, you might - though for other reasons! - end up with the same mixed feelings that you have for Paris now. IMO, it's really important to balance touristy and off-the-beaten-path locations in Italy to see what this country can be like (one way and the other), and to really enjoy it. Hence, if you follow my advice: no Cortona, this time. No Siena, no Val d'Orcia (sorry, Bob), great as those sights are, and of course, and most important of all, no S. Gimignano.
Let me come back to the hilltown question later - first, kwren's advice not to start in Florence is GREAT. Florence alone is able to jetlag you even if you came from the same time zone - it's a city full of great sights, but really exhausting. Second, one thing you didn't say much about is your level of interest for art and architecture. For a thorough and very busy (but not terribly rushed) visit of Florence's sights, you need five days. You'll need a vacation after that, but you won't be dead. So depending on how many frescoes you want to take in (and there are plenty of them, and most are really worth seeing!), you'll need three to seven days for Florence if you still want to feel like you're on a holiday. IMO, two days for the Cinque Terre are enough, but I'm not a huge Cinque Terre fan (the charm of those villages was that they were unspoiled, which means they were charming 20 years ago). I'm not trying to talk you out of the Cinque Terre, just trying to explain my position. You have to judge whether you need two or four days there. Anyway, you won't have really much time for the non-touristy part of your trip, and still I think it's important to make sure there is such a part. If you tell me how many days you'd assign to Florence and to the Cinque Terre, I'll be glad to suggest a hilltown itinerary, if you want me to.

You've already gotten a lot of great advice, AND you're very wisely using your own experiences in Paris to draft a trip that's more right for you. I would agree that 3 destinations - at the most - is appropriate for your 10 days. You said "not including travel days." Does that mean you'll have 10 full days/nights in Italy?

I noticed that you'll be travelling in October - I'm not familiar with the weather in the Cinque Terre at that time of year, but if the more-knowledgeable people tell you that the weather is more likely to be rainy then, you might want to factor that into your decision. (And maybe wait to visit the Cinque Terre at a better time of year.)

I agree that places like Siena, San Gimignano, etc. can be full of tourists. But in October, that's less likely to be the case. And we've stayed in San Gimignano several times, spending the night there, and it's delightfully small-town feeling in the evening, after the tourists are gone. People are sitting at, but not filling up, the cafes on the main Piazza, and sitting on the steps of the cistern in the middle, eating their gelatos from either of the two excellent gelaterias on the piazza. Also, in any of these towns, if you venture away from the main tourist areas, it will quickly feel less (you guessed it) less touristy. So if you decide that you really want to visit those particular hilltowns, I think you can make the experience a more local, and less touristy, one. For example, the last time we visited Volterra, we were the only people visiting the Roman amphitheatre just outside the city walls. In terms of choosing towns, I, too, would put Cortona lower down on my personal list of lovely hilltowns, but I would put Siena and San Gimignano high on the list, along with Montalcino and Montepulciano. The latter two are in the brunello wine region, so if you like wine, you might consider them (though they're definitely on the tourist radar screen).

On the jet lag; your experience sounds a bit extreme in comparison to many people's. Based on your description, and the fact that it sounds like both you and DH had the same experience, you need to change your mode of attack on the time change. Get as much sleep on the plane as possible. Skip the movie, the dinner, whatever will provide you as much sleep as you can. Some people take sleeping medications. I have a glass of wine, and that seems to help a little.

Once on the ground, DO NOT think about what time it is in Texas. Your body and mind are in Italy, and treat them according to the local time. And spend as much time as possible that first day on the move and outdoors. Keep to the local schedule; have lunch and dinner at the local time, try to avoid taking a nap, and go to sleep at the local time.

Based on your listing Florence at the top of your list, it sounds like you have particular reasons for choosing it. If so, fit it in. It's less of a favorite to me than Venice, Rome or Bologna, but I can't really say why. I love art, particularly paintings, and Florence is one of the best places for that. The ambience doesn't click with me as much as the other cities, I guess. Also, on our last trip, where we re-visited all three places, it seemed like Florence had more group tourists than Venice or Rome. My theory is that group tours, especially large one or those including people who having difficulties walking, tend to skip Venice because it would be hard to get around. And Rome is so huge, and has so much to see, that the group tourists are more spread out.

I've always found Venice, despite the tourist crowds, to be a relaxing place to visit. We spend hours just wandering on the streets and along the canals, straying very far away from the tourists center of the city (though San Marco is wonderful too). There seem to be a lot of churches and smaller places that have wonderful art to see in between wandering and sitting at cafes. So, given that you want to feel more relaxed, if you drop the Cinque Terre, maybe consider Venice.

Enjoy your planning!

Hey, wait a minute.

I realize all of you have preferences over Cortona, but I think it's irresponsible to try to talk the original poster -- who has expressed a clear desire to see Cortona, to the point of it being a mission.

She is coming to Italy to see Cortona. It is hardly any more or less "touristy" than San Gimignano!

The original poster will benefit from many points of view, and no doubt welcomes them. But some of this bordering on "take MY trip to Italy" -- and you can't seem to understand that somebody else dreams a different trip, just as pretty as yours.

I have been determined to go to some sights all over Italy -- and been disappointed when I got there. I seem to remember some people warning me I might be disappointed. But I would have been haunted, I think, had I let tourists and others talk me out of my personal 'must-sees'.

It is perfectly reasonable to want to see Cortona on a first trip to Italy. Half the reason I ever came to Italy was from seeing movies. They are no less eye-opening and instructive than trip reports, internet postings, postcard pictures and guidebooks when it comes to speaking to the soul of a traveler.

Zeppole -well said: if the original poster has a specific reason, whether inspired by a film or a book, for seeing Cortona, then she certainly should satisfy that longing. I think her most logical itinerary planning should hinge on places in the areas she is most interested in seeing. Since Florence is one of them, Cortona is a short distance away in driving time and makes sense to do in a short time and there are many hilltowns similarly close that will allow them both the city time and the Tuscan countryside and that sounds like what she's looking for - intense experience without being rushed off her feet.

Well, Louis, aren't you glad you asked?
October is a great time to visit Italy. Just lock in your dates and flight connections first--that may help to define your itinerary and timing.

I plead "not guilty"!! Here's what the OP said (among other things) about Cortona: "I don't have to see it this first trip nor do I have to base my itinerary around seeing this one town but if someone had an idea to incorporate this town and others nearby, I would take that itinerary into consideration." That's why I suggested she might be happier to postpone it to her next trip.

Okay! I back off. And I do hope Louis will get something out of this, despite having asked posters of such disparate sensibilties!

But I do think it is EXTREMELY simple to incorporate Cortona into even the most standard itinerary of Tuscany -- it's only an hour and 15 minutes from Florency by train, for heaven's sake! Even if the OP beds down in the usual Fodor's favorites of San Quirico d'Orcia or Florence, why discourage her from seeing an Italian destination with personal meaning when it is so easily done?

And Frances Mayes aside, Cortona is one of the original 12 etruscan cities, it has quite important artworks and a delightful position. I hardly see the harm of creating an itinerary to include it.

It occurs to me that whether louistraveler5 flies into Rome or Florence, making the first stop Cortona as a place to relax ad get over jet lag isn't such a bad idea. It's an easy train ride there from either city. And there is the thrill of landing in the spot of one's dreams!

Louisraveler5 could easily go to Chiusi or Arezzo from Cortona to pick up a rental car and get on with the rest of the trip.

But Louistraveler5 might embrace the idea of other itineraries, downplaying Cortona. Fine with me!

By the way, I suspect the only reason Louistraveler5 put "zeppole" in her subject line is because I live near le Cinque Terre.

Now come on, zeppole. I didn't, and don't suppose that louistraveler's question was to be read as "do I need a private jet to get to Cortona?", nor as "is Cortona one of the towns that are besieged by the Taliban?" - I thought, and think she's perfectly able to read a map, and already knew about the distance between Florence and Cortona before posting. So I would say she was asking for opinions whether it would make SENSE to include it, for a traveler with her (very candid) self-presentation. And opinions she's got, yours and others. Nobody knows which one's going to convince her, if any.
Also, please note that I didn't say a single word against Cortona; just (as I've done sooooo often) against EXCLUSIVELY visiting places where the traveler (louistraveler, in the casae of this particular thread) is going to meet more fellow tourists than she may care for. I'm advocating balance between more and less crowded places, that's all (and usually, that's nothing that upsets you, so why today?). If I misinterpreted her and Cortona or San Gimignano are more important for her than either the Cinque Terre or Florence, excellent, then she could either skip the Cinque Terre or Florence instead, and still include some quieter destinations. Or she could take up Lexma's certainly good point that in October, even crowded places are not so crowded anymore, and stick to Florence-Cinque Terre-Cortona without skipping anything - btw, no doubt that also Cortona would be a fine place to recover from jet lag since it's so small. Either way, I don't think there's a reason to be upset; perfectly true that this is not OUR trip, but it's also not our discomposure.

I'm just as stubborn as you are, franco (on the internet).

Your directive of "no Cortona" --- I am quoting you -- seemed VERY directive. But I was much more upset, however, by Lexma trying to jawbone Louistraveler5 into San Gimgignano -- of all places! -- plus Montepulciano and Montalcino in lieu of Cortona. I can accept your urging Louistraveler5 to incorporate less touristed places. But that can be done without eliminating Cortona, which -- like Pisa, Florence and Lucca and other tourist-afflicted places, still has treasures worth experiencing!

But to be simple about this, anybody who tells me, tomorrow or the next day, "I'm going to be in Italy to for 12 days -- I'll be in Cortona, le Cinque Terre and I guess one of the big art cities" -- doesn't sound to me like they are plotting an ignoramus's trip from hell. I might suggest they bed down in a non-touristy town near le Cinque Terre, given what I know about the Riviera, but I think Cortona has intrinsic worth, much like Pisa has intrinsic worth. Some people can't see past the tourist impact, but others can.

Sorry for the typo!

San Gimignano

louisetraveler5: are you still there?

Zeppole - I was providing the OP my OPINION, not my instructions or orders. It is my opinion that I like San Gimignano, and I mentioned some of the reasons that I like it (I am aware that others' opinions are different, and that's perfectly acceptable). And I pointed out that on my PERSONAL list, Cortona would be lower. I should have given more details why, so that the OP could take my comments and impressions and make her own decision. And I was not telling the OP to visit all of those hilltowns; she asked for possible hilltowns to visit.

What I have often found, in talking to friends planning their first trips to Europe, is that despite my descriptions or suggestions of less-well-known regions or towns, or their saying they want to visit less-touristy places, they seem to end up going to the more standard destinations. And when they return home, they seem to have been very happy with their choices to spend time there. Just because more well-traveled visitors may be less interested in a more well-known destination, doesn't mean that others won't love those touristy places a lot.

Lexma,

I don't think it's a matter of OPINION as to how much San Gimignano has lost to mass tourism. I think you are misleading people if you lead them to San Gimignano on the promise you taking them out of a touristy experience of Tuscany. The local culture of San Gimignano has been completely displaced by tourism. Yes, sometimes the mobs themselves aren't there -- but that is equally true of Cortona. The town isn't functioning any more as an Italian town.

Cortona suffers the same problem, but within in a 10 minute train ride, you can be in Chiusi, a marvelously well preserved and important Etruscan hilltown which has none of the downsides of over-tourism, and has significant cultural treasures in addition to the charm being entirely Italian, day and night.