September Travel vs May travel (as related to Weather and Food)

I have been in Italy in both months you mentioned. I kind of like the spring better than the fall. Everything is colorful and blooming as opposed to being dusty and golden (although it is pretty). I have also been in June, a good weather month but the tourists are on the upswing then.

So, I say spring. Try anywhere in Tuscany or Umbria for hill country food. The further north you go the more French/Swiss/German/Austrian influence you have on the food, e.g. it gets a bit heavier. Emila Romagna is the foodie capital and they have some pretty good stuff. Bologna, Parma, Modena, etc.

Beaches. Viaraggio, Monterosso al Mare are good. Some of the cool places near the ocean too, like Piombino or Porto San Stefano, but beaches are more scarce.

As far as weather, either would be fine.
But sooner is better than later.

If late May then it is probably a toss-up. Early May would not be warm enough for the beach.
Different things will be in season, but otherwise I think either would be perfect!
We loved the beach at Maremma park, but we earned the gorgeousness with a hike.
The beach at Feniglia (near Orbetello) was fantastic--sandy and natural.
The beaches on the promontory are secluded and rocky, worth it!
Around Punta Ala there are also great beaches,

.".. the most couple friendly beach"

huh?

Weather is good for either month generally.

September likely warmer.

In terms of scenery in Tuscany everything will be more green and flowering in May, it will not be that way in Sept so May highly preferred for that region if that is of interest.
For the beach though, I am thinking the opposite with May possibly too cold to lie out and definitely too cold to swim where Sept should be ideal for both.

Food I think there will be seasonal and regional options at both times, so comes down more to preference. In Italy they will typically eat what is in season and fresh.

I have spent the first 3 weeks of May and the first 3 weeks of September in Italy. This occurred in different years. Yes, everything is greener in May, but I also found it cooler and experienced more rain. Another thing I experienced in May was encountering school groups, ranging from elementary to high school ages, in all but the tiniest hill towns. i don't think you can go wrong with either of those months, but personally I preferred September.

I'm voting for May. It's my favorite time to visit Italy, and we had amazing fresh produce in the greater Tuscany area while we were there during that period.

not too many screaming roudy kids/teens

except on weekends (and bank holidays) they will be in school in both May and September.