How to Create the Perfect Italy Itinerary

As you might imagine, there are themes that come up repeatedly with the questions I get via email, on my Twitter account, on the WhyGo Italy Facebook page, and as comments on various posts on the site itself. The most common theme, bar none, is this: “can you help me with my Italy itinerary?” The post with the most comments is my perfect 2-week Italy itinerary.

The question comes in many forms, from the “here’s what I think I’m going to do, what do you think of my plan?” to the “I have no idea where to start, can you point me in the right direction?” and everywhere in between. I answer every single one of them, and I love being able to help people plan their trips. I am, however, more of the “teach a man to fish” kind of person, so rather than spoon-feed itineraries to anyone I tend to offer suggestions that still require the questioner to make decisions. (I can’t help it, both my parents were teachers.)

Here’s the thing – I’ve realized that I’m giving out the same advice in terms of things to think about when creating the perfect Italy itinerary, so I decided it was about time I put those things in one article. I will say that these are my tips for creating the perfect Italy itinerary, and someone else is likely to have different tips. But since I have no plans of becoming a travel agent and booking everything for you, this is exactly the stuff I take into consideration when I’m planning my own trips – to Italy or anywhere else, for that matter.

How to Create the Perfect Italy Itinerary

1. Get a Good Map of Italy

It may seem like a weird first step to get a good Italy map, especially if you’re not planning to drive anywhere in the country, but it’s key to the rest of the itinerary planning. The map doesn’t need to be big enough to carpet your living room or have every back road identified or anything, it just needs to have enough detail to show you city names beyond the big three, so you’ll have a point of reference for the places you want to go.

2. Make a List of the Places You Want to Go

This isn’t the time to be realistic, this is the time to write down all the places you really want to visit on this trip. I mean, you can be a little realistic, because you’d get carpal tunnel if you wrote down the name of every single city and village in Italy because you wanted to get there “someday.” You probably already have an idea of a top five or top 10 places you’re really aching to see sooner rather than later, and you know how much time you have for your vacation. Don’t worry about getting it exactly right at this point in terms of number of places vs. amount of vacation time – that’s a later step.

3. Locate the Places You Want to Visit on Your Map

Use pins, crayons, magic markers, post-it flags – whatever you like – just identify and mark all the places that on your list on your Italy map, so you can see exactly where they are in the country. This is why getting a good map is so important. It’s not enough to know that Naples is in “southern Italy” and Turin is in “northern Italy.” You have to know where in northern or southern Italy these places are.

This is critical for two reasons. First, it gives you an instant sense of what order to go in – moving geographically in one direction as much as possible cuts down on the amount of time you’ll spend in transit, while backtracking is (as I see it) just a waste of precious vacation time. (I even recommend getting an open-jaw ticket whenever possible to eliminate backtracking.) Second, it makes any cutting back on your destination wish list easier because you can see immediately what’s realistic and what’s simply not.




4. Look Up Transportation Times

This is the part where I pay the Trenitalia site a visit and start typing in city names. If you think you’ll be renting a car in Italy and driving around, however, this is the part where you’d pay the Via Michelin site a visit instead. Obviously, both of these sites are giving you estimates for journey times, but it’s at least something to use as a reference point.

Why am I so insistent about this even before you’ve narrowed down your itinerary choices? Because I want you to know how long you’ll spend on each travel day in transit. I want you to keep in mind that just saying “on this day we’ll go from Rome to Venice” doesn’t mean the trip is over in a nanosecond, leaving you the whole day to explore Venice before jetting off to Verona that evening. Getting from place to place takes time, not to mention the time spent checking out of one hotel and into another on the other end. Skipping this step may mean that you end up with only a half-day in Venice when, in your head, you thought you’d have a whole day. And that would suck.

5. Plot Out a Calendar for Your Trip

Now that you know where your desired stops are and how long it takes to get from point to point, bring in your actual allotted vacation time from stage left. I like to do this calendar-style, with big boxes for each day so I can see my trip progress; other people I know just make a list of the dates they’ll be traveling down one side of a piece of paper. Either way, start filling in each day with where you’ll be that day, and on any travel days make sure to note how long it takes to get from Point A to Point B (as per your research in step 4 above) so you’ll have a very good idea of just how long you’ll get to spend in each of the places you’re stopping in.

6. Start Cutting Back

When you run out of days, as you are bound to do, then you’ll need to start cutting back (or adding vacation days, which I highly recommend, but which most people can’t do). How do you cut back? It’s difficult, I can totally sympathize – and it has to be done. Here are some ways to make it easier:

  • Look at the Map – You have a week in Italy and you want to see Venice, Florence, Siena, Rome, Naples, Palermo, and Bari? Yeah, that’s not going to happen. And before you ask why it’s not going to happen, look at your Italy map and see how far apart all those cities are. Having that map – and knowing travel times – makes it much easier to make realistic choices when your wish list of Italian cities to visit is longer than you have time to see.
  • Eliminate Duplicates – Okay, this isn’t to say that there are carbon copy cities in Italy, or that “if you’ve seen one medieval town, you’ve seen ’em all,” but sometimes you can cut a place off your list because it offers a similar flavor to another place you’re already going. For instance, the Cinque Terre and Amalfi Coast are both clusters of coastal communities, and while they’re notably different, visiting one and skipping the other is an easy way to get a taste of coastal Italy without trying to cram too much into your trip.
  • Consider the Weather – Maybe you’ve always wanted to see Venice, but you can’t stand the cold and your trip is planned for January. Maybe you’d love to go to Sicily to see the Greek ruins there, but your trip is in July and you’re not a sun worshipper. Sure, people visit Venice in January and Sicily in July, but there are weather extremes in some cases that might make your decision-making process easier.
  • Draw Names from a Hat – This is actually the husband’s decision-making trick, and it always annoys me when it works, but it does. If you feel like you simply can’t pick between a few places, put those options in a hat (or a bowl, I’m not picky). Draw one. If you’re really excited, that’s the choice you subconsciously wanted to make in the first place. If you’re not really excited, keep drawing until you are.
  • Plan a Second Trip – Travel is a luxury, and I won’t pretend that everyone has the option of visiting Italy (or any place) multiple times. And if you’re a budding Italophile you will, in all likelihood, go back. On this trip, then, visit the places that you’d be most unhappy about missing – and then start planning your next trip with the places on the next tier down. (I usually dive into planning my next trip on the plane ride home.)

7. Now You Can Start Booking Stuff

You might be more comfortable not booking accommodation before your trip, and if that’s the case that’s fine – but if you’re like me and you like knowing where you’ll be sleeping (especially on a shorter trip when you’d rather not spend time looking for a place to stay), this is now the part of the trip-planning process where you can start booking things.

I know it’s tempting to start looking at pretty hotel pictures as soon as you make your wish list of places you want to go, but I hate it when I find an adorable B&B I absolutely must stay in and then it turns out I cross that destination off my list in the end. Once you’ve got your trip sorted out and know where you’re going and how long you’re staying, then it’s time to start looking for places to stay.


To get you started:

And there are more articles about hotels and hostels near specific landmarks in cities throughout Italy on the site – just click on any of the city names on the menu to the right, and then look in the right-hand column for titles like “Budget Hotels Near the Colosseum in Rome” or “Hotels Near St. Mark’s Square in Venice” to narrow down your choices in a flash.

Other articles you might find useful when planning your trip are my first-time visitor’s guide to Italy and this collection of Italy travel tips.

And after all of that, if you still want to ask me a question, feel free. Just know that I will still attempt to teach you to fish.

photos, top to bottom, by: alex_lee2001, enigmachck1, Alessandro Capotondi, [nivs], a hotel’s website

55 thoughts on “How to Create the Perfect Italy Itinerary

  • Debbie Thompson

    Help! The more I know the less I know. Am visiting my brother who resides (until March) in Vicenza traveling with my sister in law in October- we have 2 weeks. Since we have free accomadations trying to figure out the best plan with least amount of adding hotel cost. Any suggestions? Debbie P.S. love your website

    • Jessica Post author

      Hi, Debbie:

      Well, the least amount of hotel cost would be to spend two weeks in Vicenza with your brother and do lots of day trips from there. But it sounds like you don’t want to do just that? Honestly, I need a little more information in order to offer suggestions. You’re not giving me much to go on here! πŸ™‚


  • Joanne


    I so enjoyed your 2 week itinerary suggestions. We are planning on going for 3 weeks. Can you suggest what to add to the two week itinerary

    • Jessica Post author

      Good for you planning a 3-week trip!

      With that 3rd week, you have a couple options.

      You could keep going south from Rome – a few days in Naples followed by a few days on the Amalfi Coast. You can do that in reverse order, going straight to the Amalfi for a few days right after Rome and then backtracking slightly to Naples so that you’re closer to the Naples airport for your departure (I’d recommend flying out of Naples rather than Rome at that point on an open-jaw ticket, again just to avoid backtracking whenever possible). With 2-3 days in Naples be sure to plan one day as a day trip to the ruins of Pompeii and Herculaneum.

      Another option would be to settle in for 4-5 days in an agriturismo in Tuscany somewhere – you could rent a car after Florence, drive to a more remote area of Tuscany (or Umbria, frankly), relax in an agriturismo or a small B&B/hotel for a few days, taking day trips out into the countryside – the aimless drives through Tuscany really are spectacular, provided you have a good map & a GPS unit to take the edge off of getting lost. You could either include Siena as a day trip from that homebase, or you could drive to Siena and drop off your rental car and then continue on with the itinerary.

      There are other options, of course – time at the lakes in the north after your visit to Venice, delving deeper into northern Italy (Piedmont & Lombardy) to get into the wine regions up there, touring some of the incredibly food-centric cities of Emilia-Romagna… It’s a bit like having a pile of oysters in front of you and knowing every single one contains a pearl. πŸ™‚

      • Jessica

        Jessica (love the name, btw),

        Thank you so much for sharing the wealth of information inside that pretty head of yours! I am spending WAY too much time at night trying to glean as much wisdom from your articles as possible. But, I’m confident it will pay off, so I will keep on doing it. πŸ™‚ My husband and I (with two daughters – ages 8 and 18 mos) are spending the summer in Italy and are a little overwhelmed with all of the planning we have yet to do to see as much as we can but still get a relaxed summer (while still working, of course, because we work from wherever we are as long as there is Internet). No complaints here, though. I’m just thankful to be able to spend so much time there. Thanks again for your help! I am feeling less overwhelmed with each article I read!


  • Janet

    Hi Jessica,

    I am so happy that I found your website! My husband and I are going to Italy for the first time this august. I do want to shop a bit in Italy, and you said Milan is the best place to shop (But not worth it to see?). If we stick to your2 week ideal italy itinerary, where is the next best place to shop? Also, what is a reasonable price for a hotel in Italy? (And any suggestions of places to stay?)

    Thank you!

    • Jessica Post author

      There’s great shopping in many Italian cities, not just Milan – it’s just that Milan is the fashion capital of the country, so it’s one of the most famous shopping cities. You’ll be able to find places to go shopping pretty much wherever you are in the country.

      As for what’s “reasonable” for a hotel, it’s entirely subjective – what’s “reasonable” is what you’re comfortable paying. The prices vary significantly depending on where you are, when you go, and what level of hotel you’re considering, so I suggest you look at my article on budgeting for an Italy trip for some tips:

  • Patrick DeHeer

    Hi Jessica,

    My wife and I are traveling to Italy from 11-19 to 12-3, but I am doing some medical training in Milan from 11-28 to 12-2. We have been to Rome, Florence, Siena, and Venice before. We love Siena and Florence the most from our prior trip. Could you suggest cities that make sense to visit from 11-19 to 11-27 with us ending up in Milan for my training on the evening of 11-27? We are open to new cities and revisiting ones we have already been to also. We would like to keep travel time to a minimum. Thank you so much.

    Patrick and Mary

    • Jessica Post author

      It looks like you’ll have about a week in Italy prior to your Milan training, which gives you a few options to consider. Since you liked Siena and Florence best from your last trip, here’s what I’d recommend as possibilities you may enjoy:

      * More rural Tuscany – Rent a car, stay in an agriturismo for the week, make day trips into hill towns
      * Umbria – Hit the highlights of Umbria (with or without a car), staying in one city or splitting your time between two
      * Bologna-Parma-Modena – Highlights of one of Italy’s premier food regions (great if you’re really into food!)

      Any of these options are still within a reasonable train ride back up to Milan at the end of your week (Bologna has a high-speed connection that’ll get you to Milan in just over one hour). The weather is something to consider in late November/early December – it may be fine, but it may also be rainy/cold and not conducive to wandering medieval streets aimlessly. If weather is a concern, you might want to stick to an itinerary that has more options for indoor attractions (museums, galleries) than outdoor ones (markets, walking).

      Hope that helps!

  • Russel

    Your comments and recommendations are simply amazing and of great great help. Please keep it up.
    I have a 3 part question.
    I’ll be in the south of France mid-September (Nice to be exact) and want to go over and visit the cinque terre. I was wondering if the following makes sense to you.
    Leaving early am from Nice, arriving in afternoon at approx 1h30 and going back to Nice the next evening for my flight back home.
    – What would you recommend as the best scenic way to get there?
    – Is almost 2 full days enough to visit cinque terre, and would you recommend anything else in area as a must do/see if time permits?
    – Finally where would you recommend we spend the night in order to get a true “italian feeling”

    Again, thanks so much and keep up your great work.

    • Jessica Post author

      To start with, here is my overall travel guide for the Cinque Terre – including an overview of each town, so you can see which one you’d prefer to stay in:

      I don’t know how long the train trip is from Nice to Monterosso (which is the northernmost town, so the one you’d get to first), but I would guess that’s your best option for transportation. You should definitely find out how long the train trip is before you commit to that itinerary, however, because if it’s going to take you a long time just to get there and back then you might want to reconsider going all the way to the Cinque Terre. There are pretty coastal towns all along the Ligurian coast before you get to the Cinque Terre that may be good alternatives (and closer to Nice).

  • Linda

    Hi Jessica,
    We are planning a trip to Italy from May 18-29, 2011. Our daughter is currently living in florence and threfore our plan is to stay in florence for 5 nights. she is anxious to show us “her city.” We will do a day trip to sienna and to Chianti. We are flying into Milan and leaving from Milan because it was much cheaper to fly there than to Florence. She will meet us in Milan and travel with us. We are thinking that we would like to see Venice and Cinque Terre. Is this do-able? Do you think we should go directly to Venice when we land? We are scheduled to arrive at 9 am but midnight our time. Or should we go to Lake Como for the day, night and then leave for Venice.? How many days should we allow in Venice? Then we thought we would go to Florence for 5 nights with day trips to Siena and Chianti. Then we would go to Cinque Terre. How many days? Then to Milan and home. should we allow any time in Milan? or would it be better to go to Cinque Terre right after we land, then to florence and then to Venice? Or should we skip Venice and see Cinque Terre and Florence. Your help would be greatly appreciated.
    thank you,

    • Jessica Post author

      It sounds like you’ve got a 10-day trip, 5 days of which is in Florence, so it’s only 5 days you have to play with, is that correct? That’s not much time, so I’d really recommend you follow some of the steps I outline above – especially looking up transportation times so you know how much time will be taken up by getting from place to place. With 5 days, you can theoretically probably visit as many as 3 cities, but I’d stick to 2 if at all possible.

      You can see some of my notes regarding how much time I suggest for each stop on my “perfect 2-week itinerary” here:

  • Jer

    My partner and I are traveling to Italy for the last week of September and the first week of October. Do you have any tips on when to book the flights? Also, we were thinking of flying into Venice, taking he train to Florence/surrounding areas, exploring wine country in Tuscany, and finishing off in Rome (flying back from Rome). Would you recommend any changes to this plan? How would you divide your time in each over a 10-12 day trip (including flights, the trip will be longer than that)? Beyond Venice, Florence, and Rome, are there other places you think we should include that wont veer us far off-course? All advice is welcome. Thanks so much!

    • Jessica Post author

      For a 10-12 day trip, I think focusing on three main places is good, so I wouldn’t necessarily add anything. You can add on day trips as you go if you “run out” of things to do in the cities where you’re staying.

      As for when to book the flights, I’d start looking at fares now so you can begin to get an idea of what the prices can be. There are some deals out now for the fall, but you’ll probably find even more as we get into July. By watching the fares starting now and checking them regularly, you’ll see when prices start to go down and can jump on a good ticket when you see it.

  • velma

    hi what would you recommend for someone in Italy for 4 days. we are coming from Monaco, we were thinking of doing rome or venice and then get to Croatia. I looked at the map and think we may have to just do venice. what is your suggestion. I know 4 days is short but that’s all we have. what would be the best since we are heading to Croatia from Italy?

  • B

    Hi Jessica, I discovered your website today and it’s hands down the most useful site I’ve found on travelling in Italy! When I read how you like the format of your itinerary to be like a calendar I laughed – this is exactly how I’ve drafted my itinerary and my partner thinks I’m being OTT – but clearly I’m not alone! Can you please tell me two things: 1. If you think I’m cramming too much into our allotted time period and 2. What you think about not booking accommodation up front but leaving it somewhat to chance.
    I’ve drafted a rough itinerary as follows, however, we don’t want to set anything in stone – we want the freedom to stay longer in one place if we absolutely love it and less in others if we need to. But that means not booking accommodation in advance which is worrying me. We’ll take our laptop and try to book hotels at least 1-2 days in advance whilst we are travelling, either via Expedia, Wotif etc or just by calling places if they are recommended/not online. But will we run the danger of nothing being available, or the only available places being crazy expensive 5 star palazzos etc?
    We’re flying from Australia into Zurich late August and out of Rome late September which gives us about 3 and a half weeks in total. Current plan is to travel by train and spend 3 nights in Switzerland, 3 nights in Como, 2 nights in Venice (the one place I have been before), 2 nights in Cinque Terra, 3 nights in Tuscany region, 4 nights in Naples/Amalfi region and 5 nights in Rome. What do you think? Too much rushing around and not enough relaxing? What you said about duplicates is a good idea so I thought maybe we could drop Cinque Terra and keep Amalfi. But my partner is set on Cinque Terra and I’m set on Amalfi!
    Thanks so much :>

    • Jessica Post author

      Haha – No, you’re not alone with the calender for planning. πŸ™‚ And thanks for the kind words – I’m glad you like the site!

      I think your schedule is pretty good, actually. I’d still be sure to look up transportation times between each place so you know how long it’ll take to get from A to B (and, consequently, how much time you’ll have left to actually explore/enjoy each place) – and if you’re content with the amount of time you’ve got in each place, then that’s all that matters. I don’t like to spend fewer than 2 nights (3 if I can) in a place, so on that front you’re doing just fine.

      Regarding not booking accommodation in advance, you can absolutely do that – and yes, you do run the risk of places in your price range or the locations you want to be in being already booked. This is especially true because you’re visiting extremely popular places. It just depends on how flexible you can be as far as where you stay in a given city and how much you can spend on accommodation.

  • george

    My wife and I are looking to explore Italy in October 2011, with stops in Venice, Lake Como (possibly), Florence, the Cinque Terre, and Naples (actually, Sorrento). I’m wondering if there is any advantage to travel (by train) from Venice to Naples, or from Naples to Venice? We’re thinking of doing this over a three week period.

    • Jessica Post author

      I’m not sure I understand the question… An advantage of taking the train over another method of transportation? Or an advantage of doing the trip in one direction or the other?

  • Marianne

    Ciao Jessica,
    I have been living in Rome for a while and recently found out that I have to leave soon on short notice. I’ve not had the opportunity since i’ve been here to see anything but Rome. I am quickly trying to put together a 9-10 day trip (July) to see as much of Italy as I can before I leave. However, I am traveling alone and I am wondering if it is better to just visit 2 or 3 places and spend more time say, at the beach, where I may be able to meet people and enjoy myself longer than seeing such wonderful sights all over the country but no one to sharethem with.
    So far I have followed your itinerary suggestions but because I am alone I am really have a tough time narrowing down cities. I should first say that I am also flying out of Rome on July 25. I realize its a tough month to be traveling Italy period. I guess a big question is what is a nice beach I can spend 3 days on? I was supposed to be staying in Sardegna in Aug. and I’m terribly dissappointed I cannot now, so I am looking for a somewhat (I know its not possible) equivilent beautiful beach. I’ve heard I should try Rimidi, Bari, Livorno, and Otranto. Bari and Otranto being the only 2 that are pretty isolated from other areas I wanted to see.
    Do you have any suggestions at all for the beaches? or Traveling alone? I’m known for being unrealistic and trying to fit too much on my plate.. help?

    • Jessica Post author

      It’s too bad that you have such a short window, Marianne – because you’re going to have to make some tough choices! I think the big thing to keep in mind, as outlined in the article above, is that you won’t see everything you want to, so you’ll need to go in rough order of priority and then plan to come back someday. Even if you never make it back to Italy, you’ll at least have checked off your top priorities.

      I’m afraid I’m not much of a beach person, but my southern Italian friends rave about the beaches that line the coasts of Calabria, Basilicata, and Puglia – and of course there are beaches further north, too. If I were you, I’d first figure out which was the priority – beautiful beach & relaxation, or ticking off sights/cities on the to-do list? – and work the rest of your 9-10 days around that.

  • Lorena

    I will be traveling with a friend end of July early August. We will start our trip in Rome. We are thinking of renting a car when we leave Rome. Is it a good idea or should we consider the train? We also have heard wonders about Capri what is the best way to get there and is a one day thing enough. We are also planning to travel to Assisi, Siena, Florence, Pisa, Venecia, Verona, and Milan. What are the must sees in those places??? Thanks for the advice we want this trip to be worth it and really well planned out.

    • Jessica Post author

      There is one question here I can’t answer without more information:

      * Should you rent a car? It depends quite a bit on your itinerary. See the Italy transportation page for an overview of the ways to get around, which may help you figure out which makes the most sense for your trip:

      Capri is a fine day-trip from the Amalfi Coast, so it just depends where you’re leaving from whether it’s a good idea for your trip.

      As for things to see and do in the places you’ve mentioned, I haven’t covered every single one of them in great detail on WhyGo Italy, but I encourage you to look around the site at the city guides for Siena, Florence, Pisa, Venice, Rome, and Milan (most are linked from the right-hand side of every page). You can also use the “search” box in the right column to find things, and let me know if you don’t find what you’re looking for:

  • Bill

    Hello. Great website. My wife and I are going to Italy April 21 – May 3. 13 days. Flying into Rome and out of Milan. We want to do Rome in 2 days (limited to a few sites), Tuscany 4days, Venice 1 day to Lake Como or Lugano 2 days to Milan 1 day and then back home. This includes 3 days travel time. I want to take a train to sienna from Rome, rent a car, see some hill top towns, etc. Do we keep the car and drive to venice, take a train and then how to get to lake como? Lots of questions. Any advise would help. thanks.

    • Jessica Post author

      I’d avoid driving into Venice at all costs. If you’d like to drive around the lakes, you could swap the order of your itinerary to drive from Tuscany to the lakes, then drop off the car and take the train to Venice and stick to the trains from there to Milan.

  • mary

    Hello- tell me if this seems possible: we fly in and out of rome. we attend a wedding in positano so we have 5 days in that region. we then want to go back to rome where we have rented a car.(would it be smarter to rent a car in naples and drop it off in rome at the end?) we would like to include a stop on maremma somewhere, lucca, florence,cinque terra and bellagio with a couple days in rome at the end. should we skip something in there to include venice? following the wedding, we have 9 more days in italy.
    Please advise. thanks!
    ps: I LOVE this site! well done!! only wish i had discovered it sooner! : )

    • Jessica Post author

      I highly recommend you get out a good map of Italy so you can see where all the places on your wish list are (in relation to Positano), and then start looking up drive times (using the Via Michelin site listed in the article above). With only 9 days, I think your wish list is far too long – but you’re going to be the best judge of whether it’s okay with you to spend only a few hours in a city before you need to get in the car and move on! Getting around Italy takes much longer than you might think. πŸ™‚

  • Michael

    Hello Jessica,

    loved your itinery – but need a little help in selecting spots for our 2 week trip next June.

    So, essentials are Rome – Florence – Venice – Cinque Terra
    Next we have the lakes, Verona, Bologna, Siena, and a few days relaxing somewhere in a typical Italian village setting. We are a couple, both fit and like walking/hiking and must at some time take a boat trip (essential part of any holiday)

    So need a little guidance on a route and any other gems might have missed (Turin?). My idea was fly to Rome, on to Florence & Siena, up to Cinque Terra, either Verona or Bologna then Venice finishing with relaxing 2 days at Lakes and fly out of Milan.

    What do you think?


    • Jessica Post author

      You’ll probably expect this, but I have to say it… In my opinion, your goals are too ambitious for just a 2-week trip. πŸ™‚

      I’d encourage you to go through the steps I’ve listed above – make your wish list, look up transportation times, and start making cuts based on your priorities. You won’t be able to see everything on your wish list, so focus first on the essentials and add in other places as you can, without going overboard so much that you lose the ability to relax at all.

      Do note that the Cinque Terre may still be in a state of disrepair by next June after the devastating floods there:

      I’d encourage you to keep checking on the situation there to find out if things are open before you book anything.

  • Marie

    Hi Jessica,

    My better half and I are going to be flying into Charles De G. Airport. We have about 12 days. The thing is I’m going on R&R from a 12 month deployment and we don’t want to be too busy, that we’re disappointed by not doing everything. Do you have any suggestions about doing things, that are romantic yet must do’s and we’re not disappointed by not doing as much as we wanted? So relaxing yet memorable! I appreciate your help!

    Our original plan was CDG but not stay there, then to Venice, Rome then back to Paris and end there. Our first time. Your help is very much appreciated!

    Thank you!

    • Jessica Post author

      As much as I love Italy, if you’re flying into Paris, have to get back to Paris at the end of the trip, and only have 12 days, I’d say you should stay in France! I say this also because you say you want to be relaxed.

      There’s so much of the countryside of France that’s worth exploring, and with 12 days you could see quite a bit of it, that it seems like a shame to spend so much time in transit to get all the way to Rome and Venice and then have to get back up to Paris… My colleague Christine at WhyGo France has some tempting ideas for France:

      Have I convinced you? πŸ™‚

  • Areej Daoud

    Hi Jessica,
    First of all I have to say that your website has been the most helpful thing I’ve come across yet! (& trust me I’ve been doing my research)…everything, the little tips & details are terrific, they give such an in-depth insight into what to expect – its so exciting.
    I can take around 16 days vacation, originally my husband & I were keen on going to paris, amsterdam then go around italy around mid-June this year. After my research I realised that obviously its so unrealistic because its hardly enough time (last year we went to paris & barcelona-i only got 3 days in paris & still feel nostalgic because i feel like i didn’t get to see it properly at all). Which is why i was so determined to have it on my agenda for this year, i absolutely loved it! but after much thought I thought I’ll give it up & maybe go again next year, so I thought I’ll go to amsterdam then start the 2 week itinerary you planned, but i still feel like its not enough! do u think i should do italy only & use my extra time to visit places there?? please give me your advice!
    I really appreciate it!!
    Thanks u so much πŸ™‚

    • Jessica Post author

      Thank you so much for the kind note! πŸ™‚

      Honestly, it’s an impossible question to answer properly. You could spend years in Italy and still “not see everything,” so it’s best not to think about it that way. You’ve got time constraints, as every traveler does, so work within them. You can have a glorious time in Italy in 2 weeks, and you’ll still have barely scratched the surface – but if you’re using my “perfect 2 week itinerary” you’ll have seen some of the greatest hits of the country. On the flight home, you can start making the list of the places to visit on your next trip. πŸ™‚

  • Areej Daoud

    thank u very much for ur help jessica, I’ll definately take ur advice & use ur “perfect 2 week itenerary” πŸ™‚ thanx again

  • Lara Sullivan

    Hi Jessica, this site is terrific – many thanks. We’re looking at 4 weeks in Italy – starting in Milan, adjusting the 3 week itinerary somewhat, and ending in Sicily. Can you suggest any ‘must dos’, or fantastic experiences for our 2 kids aged 11 and 8 who’ll be travelling with us and deserve a holiday as much as we do! Many thanks, Lara

  • Alison Hall

    Hi, Love your site – full of useful info. We are two couples travelling to Italy Sept 20 to Oct 4 and would love a suggestion for an itinerary. We are flying into Rome and are planning on getting the train from Florence to Paris on the evening of the 4th. We would love to see Rome, Venice, Florence, some Tuscan countryside and also a bit of the Amalfi Coast, which we know is in the opposite direction so may be a bit difficult in the time allowed. Any suggestions would be appreciated. Happy to hire a car for some of the trip, but would prefer to use the trains. Many thanks, Alison.

    • Jessica Post author

      I don’t actually do individual itinerary planning, I’m afraid, so I’d suggest you follow the steps listed in the article above – they’re the same steps I follow when I’m planning out my own trips, in Italy or elsewhere, and they really do help!

  • Magda

    My adult daughter and I, during a two week holiday in Italy, are going to travel from Sorrento to Venice. 900 km!! I thought of doing a stop in Assisi, (450 km) sleep one night. Walk around. Next day carry on to Venice (411km)
    Best option? Train travel? (more space, more relaxing) Map of rail lines, possibilities?
    Bus travel? On route in 1 day? (900 km, exhausting?) overnight?
    Can you please help?

    • Jessica Post author

      Wow, that’s a long journey – if I were you, I’d take a look at your whole itinerary to see if you can rearrange things so as to not need to go from Sorrento all the way to Venice in one day. You can look up train schedules using the Rail Ticket Search box here:

      And if you absolutely can’t change your itinerary, you might also look into catching a one-way flight from Naples to Venice. A quick search shows that budget airline easyJet flies from Naples-Venice directly, as does Alitalia, & those flights are under 1.5 hours long. The cost will depend on when you’re traveling, but that would certainly save you time.

  • Roxanne

    Dear Jessica,
    I just found this site and am so excited for our trip in June ’12. I’m working on the itinery and would love your input. This is tenative:
    Arrive from SFO to genoa airport at 5:30pm
    June 4-7 in Monterosso (can we get to Monterosso that night, or is it too late?)
    June 7-8 Lucca
    June 8-10 Florence
    June 10-13 Rome (1 day for Ostia Antica)
    June 14 fly home
    How does that sound? we are 2 adults and 2 teens (14 and 17)
    Thank you so much!! Happy Valentine’s Day to you! Roxanne

    • Jessica Post author

      You can look up train schedules using the Rail Ticket Search tool here:

      That way you can find out how late the trains from Genoa-Monterosso run. Keep in mind that the schedules are only updated roughly 90 days in advance, so right now the best you’ll probably be able to do is get an idea of the schedules on the same day of the week as the one when you plan to travel.

  • Jody

    Great info. Jessica. Love your comments. Going to Naples in early April. 7 nts. @ Hotel Garibaldi, but want to squeeze in Sorrento, Positano, Amalfi. Love food & markets. Might consider 1 night stay some where south of Naples for convenience. Where should it be to make it logical to get to some of the more southerly sites? We don’t mind properties like the Garibaldi (clean rooms, friendly staff, good value). How do you think we should split up the trip (#s of days exploring which towns; we don’t mind train/bus commutes daily unless you think it’ll be too tiring).

  • Sarah

    My 15 year old daughter and I are traveling to Italy. We will first be landing in Paris then would like to take the fast train to Venice, Florence/Tuscany Sienna, Rome, the Amalfi Coast, then Cinque Terre area, Marseilles France and back to Paris. We land in Paris on June 5th in the early afternoon. We’d like to head to Italy right away and spend the end of the trip with family in France. So in the late evening of June 5th we’d like to be in Venice and start our trip. What would you recommend

  • Ellen

    Great site and recommendations. My husband & I, brother & sister in law & my BFF are taking a trip to Italy, They are 3 weeks, my hubbie & I are 4 weeks. We’re planning on flying into Milan and flying out of Rome. we are staying 1 week in Vogogna, Lombardy, Italy. We figure day trips in the countryside and 1 into Milano, Lake Maggiore and possibly 1 day into Switzerland. 2nd week, Siena (Tuscany)…. same approach, day trips, 1 day in Firenze ,etc. Last week or 2 is in Roma. The others are 1 week, hubbie and I are 2 weeks in Rome.

    My dilemma: I strongly believe in using trains, but for day trips you’d need a car. What do you think of using train to get to destinations and then renting a car at each destination for the week? I looked into renting a van for the whole 28 days…. and its $$$$$$$!!!! ($3000 for 28 days). However, I’m concerned that renting at each location could end up being just as much if not more. What do you think? Thanks ahead of time. Love the site… very common sense info!!!

  • F

    Hi Jessica, what a blessing for me to find your site! Your posts are so informative and interesting to read! I am planning a 3-weeks trip to Italy (solo traveler, first time to Italy) and I need your help to figure out the route of my trip. I will be flying into Milan on 9/23 and flying out of Rome on 10/14. In between, I am going to take trains to Venice, Parma-Modena-Bologna, Florence, Pisa, and Cinque Terre. Since Parma, Modena, Bologna, Florence and Pisa are in the middle continent, should I plan my destinations/route in the above order or do you suggest a better option? Also, for Parma-Modena-Bologna, I will stay at either one of those three cities for 2 nights (I am also planning to take tours to see cheese, vinegar, and ham factories (I love food!), so which city do you recommend me to stay at? Thank you so much for your help!!!

  • Sw

    Hi Jessica,

    We’re planning our 12- day honeymoon on the Italian mainland + Sardinia or Sicily starting Oct 7th. The plan is as follows – 3 1/2 days in rome, + 3 days in sicily or sardinia + 2 days in Florence + 3 days in the tuscan countryside.
    We want a little bit of everything without significant overlap – monuments, museums, fountains, squares, gardens, shopping (street and outlets), restaurants, gelaterias, concerts/opera/shows.
    ROME: Sistine Chapel, St.Peter’s Basilica, Pantheon, Colosseum, Trevi fountain, Palantine,Gardens of the Villa Borghese. – Are these do-able in the 3.5 days?

    Sicily/ Sardinia : we want to stay close to a beautiful beach. we’re unable to decide between them. sardinian beaches look gorgeous, but if the water is going to be cold, we think sicily with its ruins and other sights might be a better alternative. would the sea be too cold in the second week of october? what would you suggest?

    Florence: we’d like our stay here to be different from that at Rome. a different experience if possible.

    Tuscan countryside: We’d like to stay at a castle hotel for 2 nights and drive around the countryside for a day. Visit Abbey at Monte Oliveto Maggiore in time for the Gregorian chanting. 2 nights in the Chianti region. Basic cooking class. Attend the chocolate festival on the 19th, perhaps? we plan to leave italy on the 19th(evening) or on the 20th(morning)

    Do you have any suggestions for the above trip, Jessica?

    Thanks in advance!!!

    • Jennifer

      I’m by NO MEANS an expert, but I spent 5 days in Rome and 5 days in Florence in late Sept- early Oct 2012. We saw everything you list there in Rome… but in 5 days it almost killed us. First, the Sistine Chapel & St. Peter’s Basilica is one day, period. There is really no getting around that. Also, we went in late Sept- early October, which is STILL high tourist season. In the Sistine Chapel, you could not MOVE, it was literally wall-to-wall people.

      As for the Gardens of the Villa Borghese… again, I’d say it’s a day just to try and find the VILLA through the garden, never mind the whole estate! The garden is huge, and if you wanted to see a good portion of, but by no means the entire garden, THAT is one whole day, period. & that would NOT include time in the Villa. Speaking of, you MUST make reservations for the Villa B days in advance, and you MUST be there when your ticket says.

      Colosseum, Palantine Hill are usually doable on one tour, though that tour was probably 3 hours.

  • Sandy Rosenthal

    I am amazed at the wealth of information on your site. I have been using your guide to create my perfect itinerary. I originally thought our trip to Italy would be for around 2-3 weeks but at this stage I am up to around 35 days. I am not at the stage in my mind yet where I am ready to cull anything! I am not planning to go until 2014 and can take as many weeks holiday as I need and as I am coming from Australia I am worried that I may not get the chance to ever go back. Here is my draft itinerary – do you think I am being unrealistic and/or too ambitious?

    I am travelling with my partner and our interests are hiking, enjoying good food and wine, boating/kayaking, etc

    Venice – 5 nights, visit Verona
    Lakes District – 4 nights, either all nights at Lake Como/Bellagio or Lake Maggiore (or 2 nights at each). Hire a car here.
    Milan – 2 nights, day trip to Ferrari Museum in Maranello (my partner is an enthusiast), explore Modena
    Cinque Terre – 4 nights, stay in Monterosso. We will hike every day in the Cinque Terre.
    Florence – 2 nights
    Tuscany – 5 nights in a villa in Chianti, hire a car here and day trips to Pisa, Siena, San Gimignano, Lucca, take a cooking class,etc.
    Rome – 5 nights
    Naples – 2 nights. Visit Pompei, Mt Vesuvius, Isle of Capri
    Amalfi Coast – 4 nights. Considering staying all 4 nights in either Amalfi or Positano
    Palermo – 2 nights. Day trip to Mt Etna.

    Your input would be greatly appreciated.

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