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.

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?

2 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.

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