How to Create the Perfect Italy Itinerary for Any Trip

Goddess of Trip Planning || creative commons photo by Sunilbhar

Goddess of Trip Planning || creative commons photo by Sunilbhar

I know how it goes. You start planning a trip to Italy and you get all excited, madly pinning pretty pictures to Pinterest boards and bookmarking a whole bunch of things you want to see or do. Inevitably, you’ll end up with a list as long as your arm, and not nearly enough time to accomplish it all.

That’s when I hear from you.

For as long as I’ve been writing about traveling in Italy, the most common question I get is some version of “would you help me with my Italy itinerary?” Sometimes you’ve got an itinerary basically laid out and you just want someone else’s stamp of approval. Sometimes you’re just starting and are overwhelmed by the options. In any event, while I help everyone who writes to me as much as I can, the truth is that you are the one who’s best equipped to determine what the ideal Italy trip is for you. In order to do that, you just need a few guidelines to get started.

So, in keeping with my overall belief that you’ll get more out of your travel experiences if you do some of the planning yourself, I bring you my tips for how you can create the perfect Italy itinerary – no matter where you think you want to go or for how long.

>> Find out more about why I don’t offer Italy travel planning services

This is what I do when I’m planning my own Italy trips, or trips anywhere, really. I’ve found them to be an excellent basis for creating an itinerary, and once you’ve got the basics down you’ll make more educated decisions when you want to tweak them slightly.

Are you ready to craft your own perfect Italy itinerary, tailored specifically to you? Let’s get started.

Want something to get you thinking? Here’s my perfect two-week Italy itinerary.

Step 1: Get Yourself a Good Map of Italy

Map of Italy

Map of Italy

A geography lesson may not be your idea of the first step to an itinerary – especially if you’re going to be taking the trains in Italy and not driving anywhere – but trust me, it helps immensely.

You don’t need an intricately-detailed map with every tiny town or road on it, you just need to be able to see the locations of places you may want to go. In other words, it needs to show more city labels than just Rome, Florence, and Venice.

Online maps can serve this purpose really well, as long as you remember to zoom out far enough now and then to see places in relation to one another.

Step 2: Start a List of the Places You Want to Go in Italy

Make a list || creative commons photo by Brendan DeBrincat

Make a list || creative commons photo by Brendan DeBrincat

This is probably what you’ve already been doing, and this is the sort of “brainstorming” portion of the exercise – so jot down anything that comes to mind, whether it’s a restaurant you’ve read about or a museum you want to check out or just a list of places based on photos you’ve seen.

We all have that “I absolutely, positively must go there” feeling about whatever trip we’re planning – sometimes it’s that sort of random inspiration that makes us book plane tickets in the first place. This is the time to make sure all of those things are accounted for. I’d even suggest that you don’t worry about being too terribly realistic yet about how much time you have – you’ll have to get realistic later. Have some fun now.

Step 3: Plot Those Places on Your Map

Aspirational travel goals || creative commons photo by Caitlin Regan

Aspirational travel goals || creative commons photo by Caitlin Regan

This is when the rubber begins to meet the proverbial road. Take the list you created in step two and find those places on the map you procured in step one. Use push-pins, post-it flags, or Google’s teardrop icons – whatever suits you, so long as it’s removable.

Why bother with this level of detail so early in the planning process? There are two reasons that it makes sense.

  • You may be able to see more or less the order your itinerary should take, knowing that you want to avoid back-tracking as much as possible (it’s just a waste of your precious vacation time, in my opinion).
  • You may also get a sense of how do-able your dream list is, if you’ve got dots scattered at all corners of the country and only a week or two for your trip.

Step 4: Research Transportation Times

Watching Italy go by from the train || creative commons photo by Rhonda Oglesby

Watching Italy go by from the train || creative commons photo by Rhonda Oglesby

Now that you’ve got your dream list mapped out, you should start to see something of a route forming. This is when you open up the Trenitalia site on your computer and start to get an idea of how long it takes to get around in Italy.

I can almost hear you saying, “But wait, I haven’t even finalized my itinerary yet – how am I supposed to be booking train tickets already?” You’re not booking anything yet, so don’t worry. This isn’t about picking a departure time or reserving seats on the train, this is about being aware of how many hours it takes to get from Point A to Point B in Italy. Just knowing that you’ll start one day in Rome and end it in Venice isn’t enough information – and you’ll understand why when you look at those two cities on your map. The amount of time you spend in transit is withdrawing time from each of the places you’re visiting, and I always find that annoying. I don’t go to Italy just to sit on trains, after all.

So, yes – I believe this is an important step in the process, and I think you’ll thank me later.

Now, don’t worry about dates when you’re looking up train times on the Trenitalia site. You don’t have dates yet, you just need to see how long average train trips take between two points (including train changes, if necessary). Focus primarily on the destinations that seem farthest apart on the map, but keep in mind that some places that seem close are longer-than-you-would-think train trips because they’re not Italy’s high speed trains. Keep track of all these train times, as you’ll use it to help decide whether or not to include places in your itinerary.

Oh, and if you’ll be driving around Italy instead of taking the train, then I like the Via Michelin site for similar information – driving times, distances, and cost (gas and tolls, where applicable).

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Step 5: Create a Trip Calendar

Calendar || creative commons photo by Dafne Cholet

Calendar || creative commons photo by Dafne Cholet

Next, you’ll bring in the pesky component of time. How long is your vacation? Whatever the duration of the trip (including the time it takes to get there and back), this is the part where I like to go old-school with a calendar-style grid. I print out a sheet of paper with big boxes, one for each day, and I label the dates with a pen. Then I use pencil to start filling in the days.

And I do a lot of erasing.

(If the calendar-style grid doesn’t work for you, I also know people who put the dates they’re traveling list-style down one side of a page, filling in each day’s activities or destinations to the right. Find a style that works for you. I just think it’s helpful to be able to see the whole thing at once, on one page.)

Those notes you took in step four about transit times? You’ll put that information on the appropriate days on your calendar, so you’ll know how long you’ll be traveling on your travel days (and, consequently, how much time you’ll have that day in your start city and end city, too).

Hmm… It looks like you’ve run out of days on your calendar, but that dream list you made in step two still has stuff on it. Now what?

Step 6: Make Some Tough Decisions

Flipping a coin || creative commons photo by Nicu Buculel

Flipping a coin || creative commons photo by Nicu Buculel

Yeah, I know. Cutting some places out isn’t as fun as step two was. But, unless you’ve got unlimited vacation time, it’s a necessary step.

This is, incidentally, where I hear from many of you. How on earth are you supposed to choose what gets nixed? It’s not easy, and there are also some factors to consider that may help make it a little less painful.

  • Make priority lists. Think about how you’ll feel on the plane ride home at the end of this trip you’re planning. Complete this sentence: “I will consider the trip a failure if I have not seen ____.” Choose 2-3 things or places that meet that criteria, and put those at the top of your list. Be honest with yourself about what can be considered second-tier or even third-tier priorities.
  • Go back to step one and look at the map again. If you’ve only got a week or two and you’ve got 12 cities from Turin to Palermo on your list, you already know that’s not realistic. Seeing just how far apart those places are (step one), and knowing how long it takes to get from place to place (step four) can help make eliminating some of the places on your dream list much easier.
  • Look at weather forecasts. You may have always had your heart set on sunbathing in Positano, but if your vacation time falls in November you’re going to want to make other plans. Italy is a year-round tourist destination, that is true, but some activities and destinations are not ideal year-round. Always take Italy’s weather into consideration during your trip planning.
  • Check your calendar against Italy’s holiday calendar. Perhaps you’ve always dreamed of strolling the alleys of Venice, finding its quiet corners. If your trip happens to fall during Venice’s annual Carnevale celebrations, you won’t find any quiet anywhere. Not only that, you’ll find prices on accommodation (if any is to be found) have skyrocketed. So consult not only the Italian weather and your own calendar, but also Italy’s holiday calendar to see what might be going on when you’re there.
  • Skip any semi-duplicate destinations. I would never suggest that there are exact copies of, well, anything in Italy… And yet? If you’re looking for ways to cut back on your list of possible destinations, one way to do that is to see if you’ve already got someplace similar on the list. Maybe if Siena is a priority, then you don’t need to also visit Lucca or Cortona. Maybe if the Amalfi Coast is on your must-see list, then you don’t also need to detour to the Cinque Terre. There is something unique and wonderful about every one of those places – I’m not saying they are stand-ins for one another. I am saying that if they offer a similar flavor, then that might be a reason to skip one or the other.
  • Flip a coin, pick names from a hat, draw straws… If you really can’t decide, then make something arbitrary your decision-making tool. The thing is, you may find that you really do care in your heart of hearts – that you’re rooting for heads vs. tails, for instance – and that’s the message you weren’t allowing yourself to admit. It could be a gut-check, it could just be a quick way to make decisions. Either way, it may just work for you.

The bottom line here is that Italy has been there for many, many years, and it will still be there after you’ve taken this trip. All of the work you put into creating your dream list in step two? It’ll come in handy when you pick up where you left off and start planning your next Italy trip – maybe even on the flight home.

Step 7: Start Booking Stuff

Tickets to ride || creative commons photo by Pete

Tickets to ride || creative commons photo by Pete

Huzzah! You’ve done all the prep-work necessary, and now you can move forward confidently with booking whatever you need for your trip.

You may already have your plane tickets for Italy sorted out, and you may be one of those kinds of travelers who prefers to book lodging as you go (more power to you – I like knowing where I’m going to sleep), but even if that’s true you still probably have train tickets to buy (and don’t forget, train tickets and train reservations aren’t the same thing!) and perhaps some tours to book (city tours, museum tickets that can be purchased in advance, cooking classes or other lessons, etc.).

Whatever I book at this stage, I put the information in the calendar I created in step five. And there’s typically no second-guessing myself at this point, either, because I’ve done all the research listed above and I’m feeling confident about my itinerary choices. I find that it actually makes the booking process a piece of cake.

As an aside, while I use and love the TripIt app for corralling all the details of my travels when I’m on the road, I actually leave a cleaned-up and printed-out copy of the calendar I started in step five with my mom, house-sitter, and anyone else who may need emergency info while I’m gone. So the calendar comes in handy yet again, when you’re all done with the planning.

And if you still have questions at this point, please send them my way – I am always thrilled to hear from you, I really am. Just remember that I am wired to give you as much ownership of your trip as possible, so although I will help you make decisions that make sense for your trip, I’m still going to hope that it’s you making the decisions.

Well, what do you think? Do you have a tried-and-true method of trip planning that’s different from mine?

35 responses to “How to Create the Perfect Italy Itinerary for Any Trip”

  1. Ida says:

    I found this article quite interesting since it supplements a lot of what we have already done. My husband and I have reservations to stay in Florence arriving Mid December, spending Christmas there and ending our trip New Years in Venice that weekend. Question…we eliminated going to Cinque Terre due to weather that time of year. We want to visit Tuscany and loving wines we want to travel that region. Going to Siena is top priority as well. Which other city within the time constraints we have would u recommend visiting? Milan, Bologna, Naples? We can still change itinerary but are very interested in seeing Florence…..thoughts? Love the Christmas spirit in Europe!

    • Jessica says:

      Thanks for the note, Ida! If you like wine, you can find vineyards just about everywhere – but Tuscany is a famous wine producing region, for sure. It sounds like you’ve got about a week in between Florence and Venice, yes? If you’ll already be spending some of that in Siena, you could certainly spend the rest in Bologna en route toward Venice – it’s a serious food-lover’s city (and region). Verona isn’t far from Venice, either, and is close to the Valpolicella wine region, if you wanted to incorporate another wine-focused area into your trip.

  2. MICHELLE says:

    This is one of the best articles I have read in regards to trying to set my Italy itinerary. Myself and my friend will be in Italy from March 21 to March 30. This is my dream trip and I am the planner (she is more go with the flow). I am planning our trip not with a strict hourly schedule but just an idea of what we would like to see each day. Our flights are booked as well as hotels and train tickets between Venice-Florence-Rome (I do not have the times yet). My biggest challenge is trying to decide if we should walk everywhere, when we should take a bus or taxi and if we do that how we go about doing that. I would love to be able to send my sample itinerary to you or someone who could let me know if it looks do able or if I should start cutting some things. I still have time since our trip is not until March πŸ™‚ Thank you

    • Jessica says:

      Hi, Michelle, and thanks for the comment! I’m not a travel planner, but I do think if you’re going through the steps I outlined in this article you’ll be fine in terms of your itinerary. The big thing is that so many people forget to consider transit times, so as long as you know how long it will take to get from place to place you won’t be caught off-guard. As for the questions of getting around within a city, that depends on the city. Venice and Florence are easy to explore on foot (the outer islands of Venice by boat, obviously), but in Rome it’s handy to use the buses to cover more ground. Here’s my article about getting around in Rome.

  3. liliane ancona says:

    thank you for the information. i agree on the planning stages and drawing it out. question, we are planning 8 days in the italian lake region. spending 2 days in stresa, 3 in varenna and 3 on lake garda visiting family. we land at malpensa and have a car. should we visit stresa first or varenna. Garda is last.

    also any suggestions on where to stay. all the options on websites is overwhelming.

    • Jessica says:

      Thanks for the note, Liliane. I don’t know that it matters much which place you visit first – again, I’d look at transportation times, how long it takes to drive, and see what route makes the most sense. You might also consult the open hours/days of the things you want to visit in each town, to make sure something isn’t closed on a Monday when that turns out to be your only full day there (that sort of thing). And I’m afraid I don’t have any particular suggestions on where to stay – there are so many options, you’re right! I tend to look for places that aren’t as fancy, but still have a decent location so I can walk to the sights.

  4. Marianne says:

    We are planning to go to Italy this summer with my kids. My partner and I would like to get married there and are wondering if you have any suggestions? It would be just the 5 of us, and were thinking of Tuscany.

    • Jessica says:

      Are you asking for information about getting married in Italy, or simply the travel part? If it’s the latter, then the article on which you’re commenting is truly the best place to start. Here’s my Tuscany guide for additional information.

  5. Joann says:

    I have 7 days booked in Florence in April, 2018. It is my second trip there. I have a second week to plan and have already done Rome and Venice. Would consider Milan and Lake Como area or an easy to get to bordering country. I am pretty open to other suggestions. This year we visited Nice and Paris so those are not a consideration this time. I only want areas with public transportation or good day trips.

    I love your articles.

    • Jessica says:

      Thanks for the nice comment, Joann! Other than public transportation or good day trips, what are you looking for in a destination? Museums? Lots of restaurant options? Places to just relax? City vs. countryside?

  6. Michelle says:

    Hi Jessica,

    Thanks for this post. I’ve been a little stuck with planning an itinerary for my husband and myself for an Italy trip in April/May next year. We land on a Sunday morning and fly out the following Saturday afternoon – so not loads of time. Luckily we’ve both been before and have done all the “Holy Trinity” sites plus Tuscany. Our plan is to get a booking at a certain famous restaurant in Modena but beyond that we don’t know where we should go. I was thinking of staying in Modena and just doing day trips (to Florence, Bologna maybe, Pisa and Venice) but would you recommend spending a couple of nights anywhere else? We’ve never been to Cinque Terre or Milan or Genova or Verona, but I’m not sure if those places warrant overnight stays with such a short trip. We love food, wine and sightseeing, and are particularly keen on exploring interesting cities. Would appreciate any insight or help you could give us. πŸ™‚ Thank you!

    • Jessica says:

      If dining at Osteria Francescana is your top priority, get that scheduled first and build the rest of the trip around it, based on when during that week you can get a reservation. Personally, I’d stay in one place and do day trips, but that’s me… Though I say that partly because you’ve been before and are now on the next tier of sightseeing, as it were. Depending on when you get a reservation, if it’s not smack in the middle of that week, you could split your time between two places as home bases from which to explore on day trips. You didn’t say where you’re flying in/out of, but take that into consideration when you think about another place to stay for a few days.

  7. hi, i just found your blog after random searches to help me plan our anniversary (and first!) trip to italy. i have about 17 days or so, and when i travel i really like to get a feel for an area, not go place to place to place to mark off that i’ve been there. that being said, i want to spend actual time in cinque terre, not just a day trip or even an overnight. i want to relax, go to the beach, and enjoy the views. in your opinion, what is too long a time there? i was thinking a day to enjoy each village, while staying in riomaggiore. so actual time in CT would be 5 days. is that insane? i really don’t want to give up and plan an escorted tour that only gives me one day there, but i find this task and this trip so incredibly daunting and headache inducing. some info-May 2018, we are coming from Philadelphia, so i have to see the best place to fly into, and then basically book the whole trip around the availability of places in CT. we will not be renting a car this trip and want to use trains as main mode of transportation. as far as time in other cities, my husband is not as into museums as i am. in the louvre, we saw the big three and that’s it. b/c of this, i think i could have less time in other cities on your two week itinerary b/c we aren’t going to be spending alllll day in museums. thoughts? thank you for any insight. when i stop feeling overwhelmed, i will continue through the rest of this blog.

    • Jessica says:

      Personally, I don’t think I’d stay in the Cinque Terre for five full days, unless you wanted to do lots of hiking (the trail that links the five towns plus all the other hikes in the hills behind them) and visit nearby spots on half-day trips. The CT beaches aren’t great – the only one that’s really good for lounging on is the one in Monterosso, and even that’s not particularly noteworthy – so if beaches are a top priority the CT might not be the right destination. Having said that, the villages are lovely, and taking a few days to meander rather than power-hike through all five in one day (which is totally possible) is a much more relaxing way to visit the area.

      I hope that helps, and that the rest of the site helps you feel less overwhelmed! πŸ™‚

  8. Nancy says:

    Hi – I am just starting to plan a trip in October 2018 and am very much a novice regarding Italy. Your articles have been so helpful! it will probably be a 7-9 day trip, with at least 3 nights in the Tuscany region. Where would you recommend next? We are a food and wine loving group!
    thanks for any suggestions!

  9. alysha says:

    Hi there. What a wonderful site. I am planning my honeymoon for Oct 2, 1017 and am overwhelmed. We have never been to Italy. We have our flights booked, fly into Venice and out from Nice, France. So we are a clean slate. We love to walk cute city streets, wine, good food, shopping, sight seeing and nature (not for hikes mind you lol) We are open to traveling by car or train. We are not sure how far south to travel, or if we should stay above the map line hitting Florence as the farthest city to travel to before making our way to France. If you have any time to assist me that would be great. I am finding this trip to plan a bit out of my comfort zone. Thanks so much and greatly appreciate any response.

  10. Mark says:

    Hi Jessica, great articles and very helpful for international travel novices. My wife and I are planning our ‘kids have finally all grown up and finished school’ trip…..Italy is our place of long term dream. We are looking to go late August into September for 4 weeks in total. Planning for Florence, Rome, Naples and either Milan or Venice. Possibly a week in each location. We are going to soak up the ‘life’ of Italy and also food / culture. Based on this time of year what would your suggested travel itinerary be (i.e. if we land in Rome and depart from there what would be your ‘flow’ of travel for this time of year). Many thanks

    • Jessica says:

      The article above is really the best advice I have on planning a route, based on transit times, weather, holidays, and whatnot. I prefer not to backtrack if I don’t have to, so if (for instance) you start in Rome and end up in the north, either Milan or Venice, I’d look into flying out of one of those airports. That helps you maximize your actual time on the ground.

      • Mark says:

        Great many thanks Jessica. Would a week in each location we choose be too much or should we shorten a few of the planned spots a little and look at a few extras?

        • Jessica says:

          If you’ve already seen that there are multiple museums or attractions you want to see in each place, then a week will give you time to see them at a relaxed pace. A week also means you’ll have time to take day trips from each place, should you choose.

  11. Daina says:

    Jessica, Great travel tips. Celebrating my 50th birthday in Italy next June. First time there. Flying into Rome on a Sat afternoon and leaving Milan the following Sunday. How would you structure our trip through the Holy Trinity in terms of the number of days in each city, potential side trip if possible? Should we do a structured tour or go on our own? Do we need a car? My 2 teenage girls are coming with us.

  12. Osho says:

    Hi Jessica,

    I am visiting Italy in February 2018 from Feb 8th to Feb 14th (flying back home from Milan on 15th morning). I did definitely like to visit Venice during the carnival and murano/burano. Also, either CT or Amalfi coast after Rome and Florence. I am not much into museums and would just want to visit Rome and Florence for the touristy spots. I plan to travel through trains. I would not mind cutting out either Rome or Florence out of the itinerary completely. I am more into country-side and picturesque places. It would be great if you could help me with a proper itinerary.

    • Jessica says:

      I don’t do travel planning for people, which is why I wrote up the article above – it’s the exact steps I’d go through to plan any trip of my own. If you want to plan your own trip, I’d suggest going through the article above for suggestions on how to do that. If you want someone else to plan your trip, I can refer you to friends who do that for a living.

  13. Lisa Borghi says:

    Hi Jessica.
    Found you as the first “hit” on Google-“two weeks in Italy”!
    We have 2 weeks Sept/Oct 2018 and love your itinerary. I would
    love to see Sardinia! How crazy is that?

    • Jessica says:

      It really all depends on whether you think you have enough time to get there and back AND see what you want to see in Sardinia. Going through the steps outlined in this article, I’d concentrate on transportation times and whatever must-see list you’ve got for Sardinia to determine whether it makes sense or not. And, of course, you can always cut out something in my suggested itinerary if Sardinia takes precedence!

  14. Dave says:

    Hi Jessica, came across your posts when searching two week trips to Italy, very helpful. Just looking for any suggestions you may have in regards to what we are looking to do. We are not huge history buffs but we enjoy good food, wine, shopping, country settings and taking in nice scenery. We will be in Italy for 2 weeks starting the first of September. We will fly into Venice and will fly out of Rome two weeks later. Thinking of going Venice-Bologna-Florence-Tuscany-Rome. Does this seem reasonable to you? We would day trip from some of the City’s. It would also be nice to visit a cliff side town. Any suggestions are greatly appreciated..Thanks

    • Jessica says:

      I think the article on which you’ve commented is really the best place to start to see if your proposed itinerary suits you. It’s hard to tell what you mean when you say “Tuscany,” since it’s not a small region, but if you’ve got a rental car and just want to wander aimlessly then Tuscany is a good place to do that. (The rest of your itinerary is awful for having a car, though.)

  15. Kate says:

    Hi Jessica,
    Thanks for all of the great info! I’ve been researching and stressing until I found your blog and finally felt a bit of peace! However I wanted your opinion about booking hotels in advance. In the states we go on many road trips and always book hotels last minute just to give us more flexibility. Is this a bad idea to do in Italy? We are going in less than a week and I haven’t booked ANY hotels! The reason is I am not certain of how many days to spend in each city. My husband and I are traveling with our 2 children (4&2) for two weeks. We are starting in Paris for 2-3 days and then heading to Cinque Terre, Venice, Florence, Amalfi, and Rome. Realistically, this is probably the only time we will get to visit Italy so I want to explore as much as we can at a comfortable pace for the kids (they are used to long road trips and do great traveling). Anyways, do you think we will be ok with booking hotels as we go or should I book everything now? Any other advice for us based on our plan? Thanks so much in advance!

    • Jessica says:

      People certainly go to Italy without reservations booked in advance, so it’s not that it’s a bad idea per se… It’s just that you’ll need to be prepared to spend time looking for accommodation each day. And how tough that is will depend on where you stop for the night. You can book the next stop before you leave the previous one, too, to take a little bit of the guesswork out of it. Personally, I like knowing where I’m going to lie down every night, so I book ahead. But I’m also a hyper-planner, so that M.O. doesn’t work for everyone! πŸ™‚

  16. SRB says:

    Hi, My husband and I are flying in and out of Rome. We have 8 full days and two travel days. How would you plan the trip? Head right to Venice after the flight and travel down to Rome? Or spend half to trip in Rome and Florence and take a few side day trips? Thanks for your help….we need it!

    • Jessica says:

      I’d go through the steps outlined in the article above! πŸ™‚ Keep in mind that even if I design suggested itineraries as starting in Venice, yours can start anywhere – my overall point is to take into consideration where your inbound and outbound flights are when you’re figuring out your route. Here are some suggested one-week Italy itineraries that may help get you started.

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