Itinerary in Italy May 2026

Two nights in Sorrento will not give you time to do much, especially if you will not be departing to get there at the crack of dawn on the first day. I’d stay in one place, Rome. Or you could stay in Florence longer, or stay somewhere between Florence and Rome.
Or, if you have your heart set on Sorrento, give Rome short shrift, as it will be easy to tack on to a future trip.

It would take most of the day just to get from your hotel in Florence to a hotel in Sorrento. I'm not sure that there is value in that when you have such a short time in Italy. And 2 nights in Sorrento leaves you with very little time to see much of anything other than Pompeii.

You could take an extra night in Florence, which is still too little time there, then move to Rome. And if Pompeii is really important to you, you can go there as a day trip from Rome, albeit a very long day.

You will 'see' Venice, so unless you want to go back and leave from there, just make the most of it! If you are leaving from Rome because you want to head south to Rome and Pompeii, that will be great. If you aren't determined to do that, then I would stay in northern Italy and go to Lake Como for 3 nights, then train to Milan for a day and a night. It really depends on what you want to do and see.

I would suggest staying in Florence and doing day trips from there. There is so much to see in Tuscany and Umbria, and you don’t need to rent a car because public transportation is easy and direct. You could visit Sienna, San Gimignano, Volterra, Pistoia, Lucca, Pisa, Arezzo, the Chianti region, and on and on.

Most Florence museums are closed in Monday so you’ll probably want to stay another night there

Sorrento/Pompeii is s long trip so 2 nights there is not enough

I would recommend splitting your 5 nights between Florence and Rome

You could visit Ostia Antica while in Rome

First of all .. . unless your 100 years old or some other reason that you might not be able to travel (I'm 81 and my husband is 87 and we're going back to Italy in May as well to visit magnificent David for the 4th !!!! time), You WILL go back if you want to . . . so save Sorrento and south for another trip. (spent 3 weeks a couple of years ago in Sorrento then Sicily.) As you said, it's lovely to stay in one place and explore.

If you want another spot to thoroughly enjoy on your way to Rome. . . consider Orvieto. You will meet visitors there who stay there for months at a time. Easy train access to Rome and other small cities around. You'd especially want to visit nearby hill town of Civita di Bagnoregio, a fabulous Etruscan, now "dying" village, inhabited 2500 years ago.

"Keep on Travelin'"

I'll vote with splitting the time between Florence and Rome: Monday/Tuesday in Florence; Wed/Thurs/Friday in Rome. As already mentioned, you'd kill too much of the short time you have just getting from Florence to Sorrento.

We're all different but I try not to plan very short stays in places where almost all main activities involve the outdoors. Sorrento/Amalfi Coast/Pompeii and, say, the Cinque Terre fall into that category. Longer stays allow some flexibility for working around weather.

But I could also vote for scrapping Rome, staying in Florence for the duration - which really gives you only 4 full days and some odd sightseeing hours, depending on the larger family plan - taking a day trip or two according to whim and weather, and departing from there.

I think the consensus is Florence and Rome for sure.....but I also think Kate's suggestion is good to stay in Florence, doing the intown sites AND doing a few day trips, like Lucca/Pisa, a tour to the tinier towns, or a visit to Siena.....then train to Fiumicino (stay in the seaside town) and then fly out the next morning

You have such a short amount of time that transportation-wise, it makes sense to say to go to Florence & Rome. That’s just 90 minutes by the fast train. But, if you haven’t been to Italy previously & sounds like you won’t in the near future, I hope you can experience one of the less crowded cities, too.

I stayed in a unique street in Tivoli in May. And Tivoli is just an hour from Rome, and you could stay there before finishing in Rome. Here’s what I wrote about it:

“I rented a little apartment in the medieval section of Tivoli over the weekend for my friend joining me The terrace for this apartment, Domus Colonnato su Villa d’Este is situated out over the corner of the Villa d’Este garden - wow! (Some people waved up at us.). A fun comment: last year I had listed Casa Gotica in my TripIt plans to be sure & photograph in the medieval section. Guess what is located a few doors from this apartment!

We purchased the 3-day ticket to see Villa Adriana & S. Ercole Pincitore on Saturday & Villa d’Este on Sunday. We spent three hours at the Villa d’Este grounds - what we would consider the minimum.

Both of us thought Tivoli hasn’t received enough love on this forum. The city is outstanding to stay overnight, and the sites are well worth a couple of days, and there’s some notable church interiors! Yes, Tivoli is promoted as a day tour by many, but how about the chance to wake up in a medieval neighborhood with quirky photo moments all around & being able to enter the gardens at 9am while it’s uncrowded & peaceful with great dinner choices afterwards? : )”