Planning a vacation to Italy? Here are some things to consider:

Big constraints

Length/Time

How much time do you have to spend? How flexible is your schedule? Planning a one-week trip is much different from planning a three-month trip. Also, even if you're the most frenetic traveler, it takes time to go from one place to another, so the shorter your trip is, the fewer places you can go. Especially considering jetlag for people coming from outside Europe, I usually recommend 2 weeks minimum, but you can have an amazing 1-week trip if you are willing to make compromises (e.g. only pick 1, maybe 2, towns).

Budget

How much do you want to spend? Is this a "go as cheaply as possible" or "splurge" trip? (For example, when my wife was in college, she used things like volunteering with WWOOF to stay for free; others do couchsurfing or stay in hostels for free/cheap lodging...all the way up to expensive fancy hotels with Michelin-starred restaurants.) Generally speaking, it's more expensive to stay in central cities than on the outskirts, but if you stay on the outskirts and want to see sites in the central city you pay for it in your (likely more valuable) time. Southern Italy also tends to be cheaper than Northern Italy.

Season

What time of year do you plan to go? This can affect the weather, how much things are open, and how crowded places are. Northern Italy and mountainous regions (like much of Abruzzo) are cooler in the summer. Generally speaking the most popular sites (especially in Venice, Florence, and Rome) are most crowded in the summer. August is a bit weird, with a lot of tourists but many Italians are on vacation. The "shoulder" seasons of Spring and Fall are less crowded but still have more tourists than the winter (except winter sports areas). This advice doesn't apply as much to off-the-beaten-track trips (e.g. even in the height of summer, tiny hill towns in Molise are unlikely to be crowded). Some destinations are also seasonal (e.g. some hotels and restaurants on the Amalfi Coast shut down during the winter).

Other important constraints

Where you've already been / where you want to go?

Is this your sixth visit to Italy and you've seen all the big sights already? Or is this your first, once-in-a-lifetime trip?  Have you seen a lot of Tuscany but never been south of Rome? Or have you seen everything in Southern Italy but not the North? Are there specific places or sights that you especially want to see?

For most trips, I try to make a list with three categories:

1. Must See - Places I want to go & will be disappointed if we don't go

2. Would Like to See - Places I want to go & we should plan on going to, but if we don't make it, that's OK

3. Consider Seeing - Places that might be nice to check out if we have extra time and/or it's on the way to something else

...start with what you know already (e.g. in which category is Venice?) and add to it over time.

"Carpe Diem" vs "Relaxing"?

Everyone is somewhere on the continuum of "adventurous exploration trip" to "relaxing unwinding trip"...where do you & your traveling companions fall? As an example, my style of traveling verges towards the "let's see something new every day and make the most of our time", but my wife tends to want "let's take it slow and relax", so we usually compromise by staying 2-3+ nights in each place but trying to see 1 new thing each day.

"Must See Sights" vs "Off the Beaten Track"?

The 3 most popular destinations in Italy are Rome, Florence, and Venice, and for good reason: that's where many of the "must see" sights are....but they are crowded with international tourists, especially in the summer. Or you can avoid crowds in a beautiful hill town...but then you won't have seen the Sistine Chapel (and it might be more of a schlep to get to that beautiful hill town).

Are you comfortable driving (manual transmission) with Italians?

Most rental cars ("car hire") in Italy are manual transmission ("stick shift")...it is possible to get automatic transmission rentals, but they can be in short supply and/or very expensive. Some places (like many hill towns) are much easier to access with a car. You also have to be comfortable with the different way Italians drive; see the Driving in Italy page for some advice. 

"Planned" vs "Spontaneous"?

Where on the continuum of "I want everything planned and orderly" and "I'm OK being more spontaneous and having plans not quite work out" are you? Italy has a somewhat deserved reputation for not being completely on schedule overall (if you want that, go to Switzerland 😊), but there are ways to fit a trip more into one personality or another. In general, Northern Italy tends to be a bit more orderly / organized and Southern Italy a bit the opposite. I prefer the South (where I used to live in Naples) because I think it's more fun, but many people find it's a bit too "spontaneous" for them and it's impossible for them to relax or have fun. (Consider reading my description of Neapolitan culture and see if that excites you or scares you! ...also note that Naples is probably the most "southern" place; some other places like Puglia are less intense.)

Interests?

Italy is famous for food, natural beauty, art, history, etc...is there something in particular you care most about? For example, if you love the Renaissance, then Florence is your town. If you're into Roman/ancient history and/or Baroque art, Rome is better. If you're into food, there's good food everywhere but the region around Bologna (Emilia Romagna) is my favorite. If you love experiencing the beauty of nature, the Italian Dolomites are stunning...but some places like Emilia Romagna have relatively boring scenery.

Prioritizing Experiences

You'll remember the times you actually engaged with locals more than seeing great works of art or history. Some ideas:

• Almost anywhere in Italy: If you like cooking even a little bit, I recommend trying a cooking class.

• Going to Rome? Some experiential walking tours (e.g. going to food markets with Katie Parla's tours) sound great

• Going to Venice? I haven't tried it yet myself, but learning to row in Venice sounds amazing, or maybe a cicchetti bar crawl?

• Going to the Amalfi Coast? Folks recommend the Amalfi Lemon Experience