Italy Q&A: Itinerary Help, Please!

Carmen left this question on my Perfect 2 Week Italy Itinerary post, and I thought I’d turn it into a new post in the Italy Q&A series to answer her. She asks:

Hi, I’m planning to go with my husband to Italy in December for 2 weeks to be exact. After reading your itinerary (really good by the way) I would like to share what we have planned and ask for your opinion. We aleardy bought our plane tickets (before reading this article); so we have to start in Rome and end up in Milan.

19 December ROME
20 December ROME
21 December SIENA
22 December VENICE
23 December VENICE
24 December VERONA
25 December LAKE COMO
26 December CINQUE TERRE
27 December BOLOGNA
28 December FLORENCE
29 December FLORENCE
30 December SIENA
31 December TUSCANY
1 January TUSCANY
2 January GENOA
3 January MILAN
4 January BACK HOME

First of all, congratulations on buying an open-jaw ticket before you even read my post – it’s something too few people think of doing, but it can make all the difference in your trip. I do have to say, however, that I think your itinerary could use some re-arranging. Going from Rome to Siena is fine, but then to go all the way up to Venice only to kind of retrace your steps and head south again seems unnecessary. Is there some reason for the back and forth? Are you trying to do something specific in Venice or another city at a specific time? If not, I think your itinerary as it’s currently listed will have you spending too much time in transit.


Using the same cities you’ve got on your itinerary, and the same time spent in each, here’s what I’d suggest as a more direct one-way route:

19 December ROME
20 December ROME
21 December SIENA
22 December SIENA
23 December FLORENCE
24 December FLORENCE
25 December TUSCANY
26 December TUSCANY
27 December CINQUE TERRE
28 December GENOA
29 December BOLOGNA
30 December VENICE
31 December VENICE
1 January VERONA
2 January LAKE COMO
3 January MILAN
4 January BACK HOME

Having said that, there are an awful lot of one-day stops on this itinerary. You don’t say where you’re spending the night each night, but if you’re planning to sleep in the cities you’ve listed, that’s not just a lot of packing and unpacking, it’s a lot of transfer time spent on trains (or cars, depending on your transportation method). That kind of trip would wear me out, but it might be okay with you – everyone’s different. If it were me, I’d spend an extra night each in Florence and Siena and take day-trips into Tuscany, spend an extra night in Venice and take a day-trip to Verona, and spend an extra night in Milan and take a day-trip to Lake Como. That still leaves one-night stays in Bologna, Genoa and the Cinque Terre, but cuts the one-night stays in other places.

Anyway, those are my preferences – but again, everyone is different, and this trip may really be your travel style. Only you know that for sure! Just be sure you’re calculating transit time between cities, because you may find that you’ve got much less sight-seeing time in some places than you’d have thought.

Have a great trip, and let me know if you’ve got any other questions!

18 thoughts on “Italy Q&A: Itinerary Help, Please!

  • Carmen Maria

    Thank you very much for responding! You have helped us out a lot. We have no problem in doing your suggested intinerary because we didn´t have to much info to plan the one I sent and we´ve never been to Italy. You´re suggestions on where to sleep are very helpful as well. Do you think we can sleep in Venice but visit Bologna for the day or is it very far away? Maybe i should cancel Genoa from the itinerary or is it worth it?

  • Jessica Post author

    Hi, Carmen:

    The distance from Venice-Bologna by train is under two hours one way, so it’s definitely do-able as a day-trip from Venice. Whether you want to spend more time in Bologna, or whether you want to keep Genoa in your itinerary, depends on what kind of places you generally like. If you love the coast (even in the cold of December!), then you may want to skip Bologna and add another day onto your time in Genoa or the Cinque Terre. If you generally prefer cities, then you might want to skip Genoa and the Cinque Terre and add another day to Bologna or Rome. Bologna’s not a touristy city, but it’s great if you’re really into food. And given that you’re just arriving in Rome on one of the days you’ve got allotted for the city, I’d probably encourage you to add a day to Rome if you can anyway. (There’s just so much to see!)

    But again, you know what kind of traveler you are, certainly much better than I do. If I were taking this trip, some of the changes I’d make to your itinerary are – I’d spend at least three full days in Rome (if not four, with one set aside for Vatican City), I’d skip the Cinque Terre and Genoa (mainly because it’s December and will be too cold to enjoy the coastal Cinque Terre hike or many outdoor activities), and I’d spend a few days each in Bologna and Venice. But that may just be me. 🙂

    If you let me know more about what kinds of things you like to do (and don’t like to do), and how you’re planning to get around (car or train?), that might help me give more firm recommendations.

  • Jessica

    You are going to visit some fantastic places, but I agree with Jessica and might eliminate a one or two places, spending more days in a few key areas. Bologna is amazing and warrants more than one day for sure (you could spend one day just eating there!). I might save some of Tuscany and Cinque Terre for when the weather is better, like Jessica says. Also think that with travel you are really cutting out half days in these places. Rome could use more time (I live here so I’m biased!). In any case, I’m always of the philosophy to see fewer places better, so you don’t stress yourself out and you then feel you got the flavor of each spot. Italy north to south is so different, you should get a nice feel for that if you take your time.

  • Ava

    I just happened upon your site and, I must say, I am impressed!! I am planning a trip to Europe this summer with a friend, and we are beginning our 8.5 week adventure with 3 weeks in Italy.
    I was wondering if you could peruse our itinerary for us, and advise where necessary?

    2,3,4: Rome (we have both been here before)
    5: Travel to Capri
    6,7: Capri
    8: Travel to Florence
    9,10,11: Florence
    12: Travel to Siena
    13: Siena
    14: Travel to Cinque Terre
    15,16: Cinque Terre
    17: Travel to Venice
    18,19,20,21: Venice

    Thank you so much in advance!

  • Jessica Post author

    Hi, Ava, and thanks for your question!

    You know, I think you’ve got a really nice-looking itinerary there. You’ll have extra time on your travel days in your destination, but I’m glad to see you’ve essentially “set aside” a day for travel in each case – so that you’re not expecting more than a little time in the evening, if your trip is a long one.

    The only thing I might caution you about is the amount of time you’ve got blocked off for Venice. I dearly love that city, and could happily spend months there, but for most people it gets a little old/boring after a couple of days. There really isn’t anything to DO in Venice, aside from wander aimlessly and peek into churches, and while (again) the prospect of doing that for days on end makes me positively giddy, I know it’s not for everyone. Depending on what kind of things you and your friend like to do, you might want to add a day or two to Florence or Siena, as you could certainly occupy yourselves much more easily in either of those cities – and also take a day-trip or two if you like into the surrounding Tuscan countryside.

    Otherwise, I think you’ve got a great-looking itinerary there. Have a wonderful trip!

  • Carmel

    HEY!! i am really impressed with your thorough knowledge on Italian vacations. I NEED your help too!!! My husband and I are going to Italy for the first time for two weeks. Unfortunately, I booked the tickets before I read about your open jaw suggestion so we will be flying into Rome as well as leaving from Rome. We definitely want to see Rome, Florence and spend a day or two in Venice. The problem is that we absolutely must spend 4-5 days in Sicily. The order does not matter but I am having a very hard time coming up with an itinerary to accommodate Sicily. Can you help me??? Thank you!

  • Jessica Post author

    Hi, Carmel:

    Let’s see, two weeks in Italy, & you want to see Rome, Florence, Venice, & spend 4-5 days in Sicily? That’s definitely do-able. Since you’re flying in/out of Rome, I’d suggest bookending your trip with 2-3 days in Rome on either end so that you’re not rushing in or out just after you arrive or just before you fly out again. Some people don’t mind doing that, but personally I hate adding that kind of time-stress right at the beginning or the end of a trip.

    Here’s what I’d suggest for an order:
    – Fly into Rome, spend 2 days
    – Train to Florence, spend 3 days
    – Train to Venice, spend 2 days
    – Fly to Palermo, spend 5 days in Sicily
    – Train to Rome, spend 1-2 days before flying home

    If you can’t find a decent price on a budget airline flying from Venice to Sicily, you can take the train (there are likely overnight trips for such a long journey, although even overnight trains don’t always make it easy to sleep as some require mid-trip train changes!), but since that’s a long trip it’d probably mean cutting a day out of one of the other places on the list.

    Another option to avoid an in-country flight might be to head straight for Venice after arriving in Rome, then go to Florence and then Rome (where you’d then spend a couple days) before taking the train to Sicily. Either way would work, it just depends on what kind of trip you want to take.

    Here are a few posts I wrote which might be helpful:

    Those destination pages have oodles of links to other posts I’ve written, including what to do, where to stay, & how to get around.

    I hope that helps!

  • Sindie


    I was just searching for ways to travel better and stumbled upon your site! I will be travelling to Italy from 20th December until 6th January. I’ve never been there before and would really like you to help me map out my trip so I can get the best out of it. I’ll be landing and leaving from Rome. Please help!



  • Jessica Post author

    Hi, Sindie:

    Why don’t you email me (italy [at] with some more information about the kinds of things you like to see/do when you’re on vacation so I have a better idea of what to recommend to you.


  • Mike

    I am planing with my wife to to go 1-st time to Italy and here is my potential itinerary. Any recommendations?
    One day I like to do country side trip to see Tuscany, should I rent a car or take organized day trip?

    Day # Date Place Night
    1 Sat 3-Oct Land in Venice (1/2 day) Venice
    2 Su 4-Oct Venice Venice
    3 Mon 5-Oct Venice1/2 -transfer to Padova Padova
    4 Tu 6-Oct Padua 1/2 – transfer to Ravenna Ravenna
    5 We 7-Oct Ravena 1/2 – transfer to Florence Florence
    6 Th 8-Oct Florence Florence
    7 Fr 9-Oct Florence Florence
    8 Sat 10-Oct Florence (day trip country side) Florence
    9 Su 11-Oct Florence 1/2 transfer to Siena Siena
    10 Mon 12-Oct Siena 1/2 transfer to Luca Luca
    11 Tu 13-Oct Luca 1/2 go to Cinque Terre Cinque Terre
    12 We 14-Oct Cinque Terre Cinque Terre
    13 Th 15-Oct Cinque Terre travel to Rome Rome
    14 Fr 16-Oct Rome Rome
    15 Sat 17-Oct Rome Rome
    16 Su 18-Oct Rome Rome
    17 Mon 19-Oct Rome – side trip Rome
    18 Tu 20-Oct Rome Rome
    19 We 21-Oct Rome -morning

  • Jessica Post author

    Hi, Mike:

    Overall, I think your itinerary looks good – if a bit busy, especially for a first-time trip to Italy. I’m not sure, for instance, why you’d spend one night in Padova & then one night in Ravenna? You can do Padova as a day-trip from Venice, which would be a little more relaxed. Same thing with your one night in Siena followed by one night in Lucca. Both places are lovely, but getting from one city to another (not to mention all the checking into a new hotel & figuring out how to get around that goes with arriving in a new place) will eat up a part of every transfer day, taking away from your sightseeing time. If there isn’t something in particular that’s making you move hotels those nights, I’d say you might want to do Lucca or Siena as a day-trip from Florence, and stay in the other place two nights instead.

    As for whether to rent a car or take an organized day-trip into the countryside, you don’t necessarily need to do either. You can pick a smaller town that has a train station and do a day-trip there from Florence (there are also some good day-trips from Rome, including Umbrian towns). If you want to explore more than just one small Tuscan town and you’re comfortable with the idea of driving in Italy, then it’s definitely an excellent way to see the region. If you’re not comfortable with the idea of doing the driving, and you want to squeeze in more places than just one train-trip to one town, then an organized day-tour is another good option. It just depends on what you’re comfortable doing.

    Hope that helps!

  • Mike

    Hi Jessiaca,
    thanks for your recommendations. I think you correct about Padova as day trip.
    Reasons that I planed to spend nights in Lucca and Siena to see them when most of the tourists gone.
    What is your opinion of Cinque Terre in middle of October. Should I do it? Should I plan to spend night or go back to Lucca?

  • Jessica Post author

    The Cinque Terre could be lovely in mid-October, or the weather could be a little on the damp side. It depends on why you’re going there – to do the hike, or just enjoy the towns? If it’s the hike & you don’t want to do that if there’s going to be the possibility of rain, then you might skip it. If it’s just to see the towns & do the hike if the weather’s good, then sure – go. They’re pretty even in stormy weather.

  • Soph

    Hi, My partner are going on our first trip o/s and well what better place to start than in Italy and finishing off in Paris! We figure with all the stuff to see we hopefully wont get sick of each other! We are arriving on the 18 Dec – 17 Jan. I was wondering how cold is it and are alot of the attractions closed at this time? Our itineary is as follows. Any suggestions or improvements…
    18 Rome
    19 Rome
    20 Rome
    21 Rome
    22 Rome
    23 Rome
    24 Florence
    25 Florence
    26 Florence
    27 Florence
    28 FLorence
    29 Florence
    30 Venice
    31 Venice
    1 Venice
    2 Venice
    3 Verona
    4 verona
    5 Milan
    6 Milan
    7 Cinquere Terre
    8 Cinquere Terre
    9 Cinquere Terre
    10 Milan – Paris
    11 Paris
    12 Paris
    13 Paris
    14 Paris
    15 Paris
    16 Paris

  • Jessica Post author

    Hi, Soph:

    I think that looks like a good itinerary overall. The only thing I might change is I’d put the Cinque Terre between Florence and Venice so you’re not back-tracking south after Milan. That way you can just go straight from Milan on to Paris.

    I would offer one caution re: the weather, and it also has to do with the Cinque Terre. What are you hoping to do there? If you’re hoping to hike the trails, you might be really disappointed in the weather. If you’re just interested in hanging out, then it’s probably fine. It’s just good to be aware of the weather before you commit to the trip to the Cinque Terre, since it’s not “right on the way.”

    Now, as for weather. I’d recommend you look at my articles on weather in Italy, Italy in winter, Italy in December, and Italy in January. All of that should help give you an idea of what to expect in general, but be sure to check the actual weather reports for the places you’re planning to go right before you leave!

    You might also be interested in my Italy travel tips page for your overall trip planning.

    Have fun!

  • tania mousaw

    Question for Jessica – A friend and I want to travel from Siena to Rome by train during a trip this October. I am told there are “Mainline trains” that make several stops along the way, and a “fast” train that goes direct. What is the name of the “fast train” if it exists? I have a tour company making reservations and want to be sure we get the right train. Also, do you know cost one way?

  • Jessica Post author

    Hi, Tania:

    Thanks for your message. You’ll find the names of the different kinds of trains in Italy on this page:

    You can get an idea of the fares on trains by looking up the route you’re traveling on Italy’s train system website:

    You’ll have to put in some random dates in the next couple of weeks, because your actual travel dates are too far away. But it’ll give you an idea of what to expect cost-wise.

    And if you don’t mind me asking, how come you’re having a tour company book your train tickets in advance? It’s very easy to buy them when you’re in Italy, and that way you can also ask the ticket agent which train is the fastest option for you. You’ll also be able to book reservations on those fast trains (the fast trains always require reservations in addition to tickets), which is handy because if for some reason you decide to take an earlier or later train and you already have your tickets and reservations purchased, you won’t be able to change your itinerary. Your schedule is more flexible if you book your reservations when you’re there.

    Just a thought. 🙂


Comments are closed.