3-4 day trip to Italy

Hi James -
Realistically you have 3 nights in Italy. That is only enough time for 1 location: Rome.
I wouldn't even think of taking trains from Vienna as it's too far.

Day 1: fly to Rome; partial day in Rome; sleep in Rome
Days 2 and 3: Rome; sleep in Rome
Day 4: partial day in Rome; fly back to Vienna (if possible as I've no idea about flights)

There are a great many things to see in this city - far more than you can do over 2 full days and parts of 2 others - but what works for you depends on what you are interested in. You will also want to pre-order tickets for the most popular of attractions.

You might be able to squeeze in Florence if you FLY the afternoon of the day you intended to take an overnight train.

Day 1 : fly to Rome later afternoon: sleep in Rome that evening
Day 2: Rome; sleep in Rome
Day 3: Rome; take a fast, evening train (90 minutes) to Florence; sleep in Florence.
Day 4: Florence/ sleep in Florence
Day 5: Sightsee Florence in the morning/fly back to Vienna that evening (if possible: have no idea about flights)

Since Rome to Florence is normally a 1 1/2 train ride, taking a night train is not practical. There is a night train leaving Rome at 22.50, but it arrives in Florence at 1:44, not very good time to arrive in Florence. Why not take a late train (20:20 or 20:50), or a very early train the next day (6:05)? Pisa back to Vienna is a late train to Florence and then get the night train back to Vienna.

I agree, this sounds too tight to see two cities let alone 3. You should consider flying to Rome, staying in Rome and then flying home on such a tight schedule.

Day 0: Evening flight to Rome (3 nights)
Day 1: Rome
Day 2: Rome
Day 3: Early morning train to Florence (1 night)
Day 4: Early morning train to Pisa. Afternoon flight to Vienna

I've been to Italy 3 times but never to Pisa and it is not on my bucket list. On the other hand, every time I go to Italy, I increase the time I spend in Florence. Fly to Rome, visit Colesseum and Forum the afternoon you get there. Next day to Vatican then take late PM train to Florence. That leaves 1 1/2 days for Florence before train back to Rome to fly back to Vienna.

Another possibility, stay in Rome entire time and take day trip to Florence-leave early AM, return late PM.

The night train from Vienna is a great idea:

Wien Hbf 19:23 13:59 0 EN
+ 1 Day

Roma Termini 09:22

Rome to Florence is 1:30 at most - take a late train and check into your Florence hotel - then you are settled in and ready to take Florence by storm!

You can do a "day trip" to Pisa from Florence and return to Florence for the night train to Vienna

You can take the night train back to Vienna from Florence:

Firenze S.M.N. 21:49 10:57 0 EN

+ 1 Day

Wien Hbf 08:46

Arrive Rome, day in Rome, sleep Rome
day in Rome, late train to Florence, sleep Florence
day in Florence, sleep Florence
day trip to Pisa, return to Florence for night train back to Vienna

I would spend your time in either Rome or Florence.

Spend all your time in one place. It always takes longer to relocate than planned and that is time that is just plain lost. And you really don't have enough time to lose any of it.

I will never understand what takes so long about relocating. For a trip such as this with quick stays we typically stay within a 10 or less minute walk from the train station. It takes all of 5 minutes to check-in to a new hotel and 30 seconds to check out - I usually just drop the keys at the front desk, tell them the room number and that I do not require a receipt. If I need to still settle the bill in the morning I do this before breakfast.

We do not ever "unpack" on a quick trip - items are taken out, used, then returned to the suitcase. It takes about 5 minutes to be ready to walk out of a hotel room to check out.

I guess if yopu have never traveled with a fast moving itinerary it may seem difficult to do but it really is not.

Time lost for relocating at most:

10 minutes walking from/to train station
5 minutes checking in/out of hotel
10 minutes arrival before train departs

Not much really - we can usually do it in less time.

Everyone has their own style - do what works for you. If you want to hit the highlights in each of these places it is very doable. If you want a relaxing mini-trip then stay in one place for the duration.