We'll be in Rome and Calabria this spring. Will report back here as to crowdage if they let me out of Al Fodoria prison.
I am done. the vanishing shoulder seasons

We always prefer September in Europe.
Both May and September are beautiful weather, a bit less tourism, but we have found September to have all the flowers, etc.in bloom, so a lot prettier than May when they are just starting to flower.
Just one traveler’s opinion!

Thanks all! I really appreciate it. I actually am helping my son plan his honeymoon. They are thinking about 8 full days on the ground -- arrive on a Friday morning and depart the following Sunday.

Ideally, they want to experience Rome and then go relax on the Mediterranean somewhere. I think they need to avoid the Amalfi coast and Cinque Terre due to insane crowds. My husband and I loved Santa Margherita Ligure two decades ago and Camogli looks charming but I hate for them to waste a day traveling up to the Italian Riviera. My husband and I were in Forte di Marmi two decades ago but I just don't know much about the Tuscan coastal towns.

Anyway, just starting to help them (and plan my own 2025 trip as well!)

I has originally told you I had a slight preference for May over September, as I felt there was a
​​​ better chance of good weather. However, if you are looking at seaside stays, I want to warn you that the water is usually still very cold in May. If you just want to look at the sea, it's fine.

There are some beautiful Mediterranean locations closer to Rome than the Ligurian Coast. The easiest to get to is Sardegna. I would also consider Elba, or one of the very small islands off the coast of Tuscany, for instance Isola del Giglio. If you're don't want to find an island, there are some very nice spots in Tuscany. The Argentario Promontory has some very nice spots, and you can visit the Isola del Giglio from there. The Maremma Regional Park has some beautiful non touristy relatively undeveloped beaches.

South of Rome, I would consider Gaeta, or (another island) Ischia.

None of these places are overrun by tourists, although beaches will start to be a bit crowded, at least on weekends, by the end of May. And if the weather is as hot as it was in 2023 in September, the beach season will be prolonged well past August.

If I don't injure myself, we're going Rome/Naples in May next year, and Northern Italy in mid-September. Personally my favorite traveling time frame is mid-September through early October, especially if we're in wine country.

Last year northern Italy (Lecco, Como, Bergamo) was hot at the end of May, hot being 25, whlie in southeastern MA it was a cool 18. Greece was hot too but it was bearable, at least, and the island we went to was hot too. There’s no shoulder season anymore. Meanwhile my FIL has had 28 this week in Calolziocorte.

We see Tom running head-down/full-speed directly into a cactus. A large one.
I am done. the injury

25? I know plenty who will be wearing a jacket.

25 is the ideal temperature. If it's cloudy or windy, I might need a jacket or cardigan.

Italy has some real weird weather year round. I would suggest you visit central and southern Italy during may and Northern Italy in September.
If you visit Milan or Venice in May it might get a bit cold to fully enjoy the trip and if you visit Sicily in September you will be miserable with the heat.

The whole world has weird weather lately.

Sicily can be miserably hot even in May. This year there was summery weather already in February. Some of the beaches were full of sunbathers.

On the other hand, I think May would be fine for a visit to Milan and Venice. There's a fair chance of rain, but it's unlikely to be very cold.

amen to that

Albeit a while ago, we went in May to Venice, Cinque Terre, Tuscany, Florence and found it to be a great time to be there.

It honestly really depends on what temperature a person prefers, if they're fine with temperatures as low 55F then it would be great to visit Venice in May. I found Sicily was bearable in May compared to September when it got hotter than 80F, I was dying then.

Last year, the average high temperature for the month of May in both Venice and Milan was 73 degrees (Fahrenheit). The average low temperature was in the mid-60s in both cities. I live in Italy and I wouldn't expect to find 55 F temperatures in those cities. It could happen, of course, but I wouldn't plan a holiday anticipating those conditions.

I agree with late May. September will be more crowded and hot

A jacket for 25c? 😂. Where we live even when it’s 25 it doesn’t feel like it because of the constant winds which usually average 15-25 on any day of the week. We’re heading to a few Greek islands this year, bookended by our usual Italy family visits.

I love both times, see no problem with both dates.

Of course it might not get that low, but if someone is not used to colder climates then even 60F might be a bit cold to them. Imho Venice is pretty and enjoyable even in cold ass winter. I could go there any time of year, it's beautiful.

An average low temperature in the mid-60s doesn't mean you can expect to be walking around at a temperature of 60 degrees. The average low temperature is usually reached at around 3 AM.

By the time you're up and about, the temperatures would probably be in the high 60s or low 70s.

Of course, as I said before, it's always possible that there would be an unseasonable cold snap. These days it's even more likely that there would be an unseasonable heat wave.