First trip to Italy in May

Note that your first and last days of any European trip will be essentially wasted. And every time you move from city to city will be a lost day. And 10 days is really not enough to take in as much of Italy as you're showing.
I suggest you fly into Rome for 4 nights, move up to Florence on a fast train for 3 nights and the balance of your time in Venice--flying out of there.
Getting all the way to Milan is just too much for the time allotted.

I would go

4 nights Rome
Train to Florence
4 nights Florence
Train to Milan
2 nights Milan
Fly home
Rick Steve's covers all the must sees under Italy in his videos. You can get a lot of ideas and instructions on what you want to see by watching those free videos or getting the guidebooks
https://www.ricksteves.com/watch-read-listen/video/tv-show

Note that your first and last days of any European trip will be essentially wasted. And every time you move from city to city will be a lost day.

I never feel moving from a city in the same country as a lost day, depends on the person. The first day can feel a little surreal after flying all night.

Steve-
Just got back from a “first trip”myself. I spent two weeks in Italy. I started in Milan and had a car, but we went to two smaller towns neat Torino and Milan to look up family history. Car was a must for us for those places. My last three nights of the first week was in Bellagio at an apartment just outside the limited traffic zone. It had onsite parking. We never used the car for Bellagio except to arrive and leave. The center of most smaller towns and cities will be very walkable and in some cases only walkable. Depending on where you decide to go, you might find a car more of a problem than a bonus. Driving between cities is great on the freeways, but in cities and even smaller towns, driving can be an issue with Limited Traffic Zones and parking. Use known garages in big cities and be aware of tolls on the highways. Make sure your hotels offer parking and what they charge. Driving between Milan and Torino was a breeze with Google Maps but really plan on the routes and how much time you spend in the car. Download your maps first so you don’t have to use data.
My second week was solo and the trains make travel much easier. I downloaded the Trenitalia app and purchased all of my tickets online. My second week was in Florence, Bologna and Venice with a final night in Milan before my flight out.
I also opted for the service Wi Tourist. It’s a handy mobile WiFi device that uses cell data to create a hotspot for WiFi. It’s more expensive than a data plan or getting a chip for your phone, but I had unlimited 4g data for two weeks and it handled up to 10 devices at once. Make sure you compare plans, but it worked like a breeze for me.
Whatever your plan ends up being, make time to stop and enjoy yourself. Try the language (you’ll find English everywhere) and branch out from the pizza and spaghetti (I actually ate horse on this trip).
Good Luck and Safe Travels!
Jeff

Basic principles of trip planning:

1) Count nights, not days.
2) The day of departure is taken up with getting to the airport.
3) The day of arrival is often a jet-lagged haze, so don't plan anything important on this day.
4) Two nights in a place equals one full day. Three nights in a place equals two full days. And one night in a place is less than a full day.
5) Don't focus on what you can't fit in. Accept, right now, that something you really want to see will not work out on this trip, for one reason or another.
6) While it's great to get others' recommendations, be sure your trip is what YOU want to see and do. Don't go to a place just because "everyone" goes there, or some book or website says it's a "must see" (or even worse, "must see before you die"). With only 10 days, if a place doesn't make it to your personal A-list, it's out.

Specifics for Italy:

1) It's often easiest to see Italy in a line, north to south or vice versa (you've got the part covered).
2) Italy is insanely dense with history and worthwhile places, sights, artwork, food, etc. In ten days, you can only see a sliver, of a fraction, of a portion, of the country. Accept this now. Don't try to add more than can be reasonably seen and enjoyed in your very short time. And be careful of well-meaning people who say, for instance, "if you're going to Florence, you simply have to see Bologna too, because it's so close." "if you're going in Bologna, don't miss Ferrara." "If you're going to Ferrara, be sure to see Ravenna too." Pretty soon, you will have a great two-month trip - except you only have 10 days. Yes, all these places are great, but you have to ruthless in putting places on the "next trip" list.
3) A car is handy in Italy for small towns and countryside. It is an absolute liability for cities. So, before you plan on renting a car, make sure your itinerary is best served by driving. Or, conversely, if you're committed to driving, make sure you're seeing places that are easy with a car. For instance, if you want to go from Rome to Florence to Milan and stay in those cities, don't rent a car, or you'll be sorry (really - search the forum for posts of problems for the unwary driver in Italy). If, on the other hand, you want to go from Rome to small towns in Tuscany and Lombardy, only going to Milan to catch your flight home, then a rental car between Rome and Milan makes sense. If you want to stay in an agriturismo (farmstay), then a car is a near-necessity.

And most important: Assume there will be a next trip! Otherwise, you'll drive yourself crazy with what you're not seeing this time.

Hi Steve,

I wish I had read Harold’s post before I took my trip last late May/June to Italy with 6 people, 6 of whom had never been to Italy. I will add a couple of lessons learned from our trip and a recommendation.

Lessons:

• Everytime you change locations, you can burn up to 1/2 day in travel, factor that into your travel plans.
• If you are going between cities, long distances take the train. It is fast and efficient. We rented a car to explore Tuscany and it was worth it, especially since we stayed in the countryside. Driving is straightforward, the only issue for us was navigating parking (too big of a vehicle and limited parking in cities such as Sienna).
• Don’t jam your intineary, eveything takes longer than you think and it is great to have breathing room in your trip.

In the amount of time you have going to Rome, Florence, and Venice is one plan, the other is to go to Rome, Florence, and Milan.

Italy is an amazing place to visit. Have a great trip,
Sandy

I agree with others that Rome, Florence and Venice are the 3 best cities in Italy. However, It will be tough because you only have 8 real sight seeing days. You will loose one-half day traveling to Florence and another half day Florence to Venice or Milan. Why drive? It will add to your costs, you'll get lost, it will be a hassle to park (no parking/cars in Venice!!!), you'll eat up more valuable time and the driver is always the person who sees less of the countryside. Consider trains. Rome-Florence is a 3 hour train ride as is the Florence-Venice route. Sit back and relax and enjoy train travel. Milan is nice, but IMO not as great compared to Venice. Your hardest decision is what to see in Rome and Florence. Book tickets to museums ahead of time and skip lines. PS...If you can add a couple extra days, do it. Enjoy your trip.

Actually, the trains on the Rome-Venice line are much faster than Threadwear remembers. The trips can be as short as:

Rome-Florence: 1 hr. 16 min.
Florence-Venice: 2 hr. 5 min.

By comparison, ViaMichelin estimates the driving times (no stopping, getting lost, searching for parking, etc.) at:

Rome-Florence: 2 hr. 53 min.
Florence-Venice: 3 hr. 16 min.

So driving takes roughly twice as long, in aggregate, plus there's the time spent dealing with the rental agency on both ends.

Steve,

Is there a reason you want to fly out of Milan?
Some place you want to visit?

A common first trip would be to fly into Venice, much softer intro to Italy, then train to Florence, and ending in Rome. Allocation of days would depend on what you want to see in each city.

Thanks for the double check acraven. Even better for the OP to utilize trains.

I forgot to mention some things (reminded by posts above):

You lose a half day when you change locations, even close together ones like Florence and Rome. You lose more of a day with further location changes.

While Rome and Milan get most of the nonstop flights from the US, Venice has "seasonal" flights from O'Hare on American. In May, these flights should be operating, but I don't know if they are daily. Flying into Venice and out of Rome, as someone said above, is a great outline for a trip, and particularly with such a short trip, you don't want to detour to Milan unless you are seeing places near it (such as Lake Como or Lake Maggiore).

Furthermore, with a single plane change, you can get from Chicago to any airport in Italy. If, for instance, you want to focus on Tuscany, there are airports in Florence, Pisa, and Bologna (this last is just outside Tuscany, but close enough to use). All of these get flights from various European airports, and may work better for your itinerary. Or round trip to Rome may be best if you're only seeing Tuscany and Rome.

While Rome, Florence, and Venice are the Big Three for a reason, there's no law that says these are the three places you have to go on your first trip - particularly with only ten days. My first trip to Italy was Milan, Venice, and Florence, with side trips to Siena, Lucca, and Pisa. People were scandalized that I didn't go to Rome, but it just didn't draw me. However, on the trip I got a yen to go to Rome, and did so on my second Italy trip. It's now one of my favorite places. But who knows how I'd have felt if I had only gone out of obligation rather than genuine desire to see it?

So, don't book any flights until you've figured out what you want to see, and be flexible as to destinations and look at all flight options before buying.

Wow everyone -- thank you for all of the great tips.

The car thing is more about flexibility of itinerary, but I get the point that sometimes it's more trouble than it's worth. We'll re-think that. I'll also take a look at flipping the trip and shortening the distance north to south.

Thanks again!
Steve

"The car thing is more about flexibility of itinerary"

You have ten days, so you don't have that much flexibility. Furthermore, if you're taking trains or buses on main route (say, train from Florence to Rome, or bus from Florence to Siena), these are frequent enough that you will have lots of flexibility. On the other hand, pre-booked and non-cancellable tickets will be cheaper than turn-up-and-buy tickets for fast trains, like those from Florence to Rome. Flexibility costs money; saving money requires committing to specific trains in advance. Either way works, and unlike in some countries, last minute train tickets aren't insanely expensive in Italy.

"but I get the point that sometimes it's more trouble than it's worth."

If you do want to rent a car, which does work well for rural areas and small towns, be SURE you understand all the pitfalls. You need an International Driver's Permit (easily obtained from AAA even if you're not a member, but must be obtained in the US). Certain kinds of insurance are mandatory in Italy, so the cost of a car can be high. There are speed cameras of several cameras, bus lanes you cannot enter, and ZTL's - zona traffico limatato - which are parts of city centers you cannot enter. If you speed - even a little - or enter a bus lane or ZTL - even briefly - cameras will catch you and you will get a ticket. The ticket comes in installments. First there's a fee of about about €45 - per ticket - from your rental car company for turning over your information to the authorities (you have to agree to pay this as part of your rental agreement). Then there are the tickets themselves, which often arrive months later.

You also have to budget for gas (much more expensive than in the US, although cars get good mileage), tolls, and parking.

Again, I'm not saying you can't rent a car. Just, please, don't be one of the people who doesn't do the research beforehand, then comes back here to scream and yell about how unfair all these fines are, because "How was I supposed to know all the rules?". The rules are the rules; follow them strictly and you'll be fine, deviate and pay the price (literally).

For a first trip, I would not bother with Milan.

I would fly into Venice, a relaxing place to get over jet lag. Easy to get flights into. Flights out of Venice are usually very early in the AM, and the airport is not that close.
Depending on how much time you actually have, not including the 2 travel days, you could train to Florence for 2-3 days, then train to Rome for the remainder and fly home. There are many flights out of Rome, very easy to get to the airport.

Forget the car, trains are easier and faster, and cheaper! When you return to Italy to tour the Tuscan countryside, then you can rent a car.

We have taken a lot of advice and booked our tickets, flying into Venice and out Rome. Great prices in May. We are also forgoing the rental car and doing the train. Just started diving into hotels and Rick's Italy book. So, the real planning begins.

Thanks again for all the great thoughts and experience. We appreciate it.