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Itinerary in Italy May 2026

We will have approximately 5 days in Italy to go wherever we want in May 2026. We have a family event that will give us 2 nights and 1 day in Venice, 2 nights and 1 day in Florence prior to being on our own. My husband and I will be in Florence and will do our own thing starting on a Monday. We will fly home from Rome on Saturday morning.

Right now we are trying to decide what to do. I don't know when we will get back to Italy any time soon. We were considering taking a train to Sorrento for 2 nights and going to Pompeii and then other things in the area. From there, we would go to Rome for 2 nights. I'm sad that we won't have more time in Venice but there is a lot to see and the time at the beginning of the trip is not ours to plan. I'm planning Monday lightly because I don't know when my family is leaving and there could be group activities Monday morning or they will leave bright and early. I also like the idea of being in the same place for 2 nights and not moving hotels every day. We aren't against renting a car but like the idea of skipping a car for this trip.

If you only had 5 days -
- Does this plan make sense?
- Would you stay in Northern Italy and explore more there? Do we "need" more time in Venice? I will always need more time everywhere.
- Would you do something different?

For some context, we stayed in Paris for almost 2 weeks in 2018. We switched hotels after 5 days and stayed in a different part of Paris. We loved that trip. It was relaxing and gave us a chance to explore. We had a lot of "happy accidents". We won't have that kind of time obviously and I don't know that I want to stay in the same place for the entire time either for this trip. Thank you in advance for your thoughts.

EDIT: I forgot how we ended up in Rome to begin with. Because of the flight times, we get to leave on Saturday instead of Friday. So we do need to end in Rome at least on Friday night for a 9:30am flight on Saturday.

Posted by
6202 posts

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.

Posted by
6687 posts

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.

Posted by
327 posts

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.

Posted by
765 posts

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.