May wedding in Tuscany - Help!

We have found our dream wedding venue in Tuscany and an absolutely brilliant wedding planner who can do all we want within our budget and is really pleasant to work with. We have had a less favourable experience with another planner who has quoted us a lot more for exactly the same!

The planner has given us 2 dates in mid and end of May. I am worried that given we want our guests to enjoy evenings and the unheated pool that May might be too mild and an increased chance of rain. I have always pictured a very summery wedding and I am struggling to think about paying so much for a wedding that might have bad weather.

The alternative is we could get married at our venue in June/July but without the fab wedding planner and try to find someone else to work with but I am 100% certain they won’t be as good and it will make the weekend more stressful.

Can anyone advise if May would be absolutely fine or if it really is worth loosing the wedding planner to switch to June/July and get better weather. Thanks!!