Need advice for Italy trip in May

If you do want to visit Venice, I’d suggest flying into Venice and out of Rome (are you familiar with the ‘multi-city’ or ‘open jaw’ option for booking flights?). Certainly, there’s serious crowding in parts of Venice, but it’s easy to avoid those areas during peak times, and save them for visiting early morning and evening.

Def book MultiCity Tickets. We like Venice much more than Milan. With only 10 days, fly into Venice, train to Florence, train to Rome - three nights each... Fly into Venice and out of Rome.

You can do a day trip out of Florence with WalkAboutFlorence - the Best of Tuscany tour includes Siena.

There is no where else like Venice.

If you only have 10 days, and no particular interest in Milan or Lake Como, then flying into Milan only makes sense if you have a killer ticket price. Venice IMO is one of the most unique cities in Europe, and crowds can be mitigated with adequate research. And any of the places you cited will have crowds. Flying on a multicity ticket into Venice and out of Rome would maximize your available time. This would give you 3 days in each place.

However if you also want to add day trips to Pisa and Siena, I'd limit your stays to Florence and Rome. Fly RT Rome, but continue on to Florence by train on your arrival day. Spend the last half of your stay in Rome.

I agree with Inbsig about flying in and out of Venice and Rome. If you fly out of Venice, make sure it’s a late morning flight when the bus will be operating and can take you to the airport. Otherwise, you must pay a fortune for a water taxi.
You need three nights for Venice, four nights for Florence and that includes a day trip to Siena by direct bus (1h 15m) and skip Pisa. Be sure to buy tickets for the Uffizi Gallery two months out to guarantee a reservation. Rome also needs four nights if you visit Vatican City.

Welcome to the forum!
We need a bit more info-
Who is we?
Have you traveled abroad before?
What are your interests?

How many NIGHTS do you have on the ground in Italy?
A 3 night stay means 2.5 days in that location. Usually that does not allow time for day trips,
Florence should get a minimum of 3 nights, Rome needs 4, Venice should get 3.

Venice is worth it. It is the most unique city in the world and IMO not to be missed. Everywhere will be crowded in May, there are lots of tips and tricks to avoid crowds.

Milan- if you have any interest in Milan then flying in to Milan makes sense- otherwise it is sort of an outlier. We visited Milan on our 4th trip to Italy strictly for The Last Supper. Also enjoyed the Duomo rooftop terraces, but have no need to return to Milan
Often flights to Milan are less expensive than to Rome or Venice but you have add the time/cost it takes to get to the place you actually want to be. Your trip is short- prioritize your locations.

You can fly into Venice and fly home from Rome.
Or if Venice is really not of interest then fly in to Florence (change somewhere in Europe as there are no flights to Florence from USA), fly home from Rome. Or if RT Rome is a better deal fly into Rome head immediately to Florence, put all Rome nights at end.

So until we know exactly how many nights you have to work with I will assume you have 10.

Milan- 2
Florence- 4 with a day trip to Siena
Rome- 4

Or
Venice- 3
Florence- 3- no day trips
Rome- 4

Or
Fly into Rome
Train to Florence- 5 nights- 2 day trips- Pisa and Siena
Train to Rome 5 nights
Fly home from Rome

All easily done by train
It is easier to fly IN to Venice than out of.

If you have less than 10 NIGHTS on the ground I would stick with 2 locations- Florence and Rome.

Thank you so much! My husband has been to Italy, but I am new to international traveling. We really want to see the wonderful art and architecture, and really just soak it all in. I love the idea of just wandering in Florence and Rome, seeing the things that we have wished to see, but not kill ourselves trying to do it all. It's during our Anniversary, so we want it to be special, and not grueling.

If you truly have 10 full days (not counting days spent flying in and also flying out) , I would spend five in Rome , 1 day for train travel between one other city, (Venice or Florence) and 4 days in that 2nd city.

I think most of us find it can be challenging to be realistic. It’s easy to underestimate the amount of time it takes to get “situated” in a new destination, time it takes to get to a train station and on the train, get checked into a hotel or out of a hotel, etc.. try to plan time for those things so that you are not in a frenzy throughout your vacation.

My vote is for flying into Venice and on to Rome , flying out of Rome. But you can’t go wrong. All of those places are lovely. Enjoy!

You really should study what's of interest for you in every city. Just wandering around such premier and important cities might be a waste of time that you could use seeing the sights.

If at all, try to grab a few more days. Italy's got so much art, architecture food and culture that you need to travel slower.

Venice and Florence are both 3 day minimum cities. Rome has so much to see that it's a 4-5 day city at the minimum. And even the Rome suburbs has many, many things to see.

You cannot do much about the crowds--other than hitting the tourist trail very early in the mornings.

Siena is best traveled to by bus from Florence, and the buses line up to the right side of the McDonald's Restaurant out the side door of the Florence train station. They take you directly into the center city of Siena.

With only 10 days, choose two places and split your time.

Into Venice, out of Florence.
Into Florence, out of Rome.
It really isn’t enough for 3 cities especially if you want to do a day trip or two out of Florence. Then I would definitely go onto Venice, spend 3-4 nights and spend the remainder in Florence and leave from there.

Otherwise, if into Florence and out of Rome, I would be tempted to only take one day trip from Florence, then maybe one day trip from Rome. I think once in the cities, it will be hard to tear yourselves away from all they offer.

Besides, you’ll most likely fall in love with Italy and go back any number of times!

This is all very helpful thanks!