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.
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.
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.
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.
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).
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?
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.
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.
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?