Getting Married a few days after tourist visa expired!

Hello,
My Brazilian boyfriend and myself (I have dual citizenship: Italian and Brazilian) decided to get married while he was visiting me on a 6 months tourist visa (he arrived on 22nd December 2016).

We've been together for 2 and half years - both of us travelling back and forth between Brazil and the UK over this period to meet and spend time with each other.

We gave notice at my local council and received a letter from the Home Office that they will not conduct an investigation and that we are allowed to marry after the 28 days notice have expired.

Obviously getting married in the UK in June and with such a short time to organize the wedding isn't an easy task. (We only received the letter from the Home Office on the 9th May - so we didn't do any planning till then - as we didn't know if we'd be allowed to marry after 28 days or only after the 70-days investigation period).
So we've been having issues finding a venue that we like, can afford and that is available on a Saturday before his visa expires.

It will be a small celebration (around 30-35 people), but nevertheless it is a special moment for us and we don't want to marry anywhere or on any day (we wouldn't want to marry on a week day for example - as a lot of our friends would be working or people would have to rush to the wedding - as opposed to it being a special day for us and our friends.). Plus we have close family coming from Brazil - so we need to allow time for them to organise themselves to travel to the UK for the wedding.

We found the perfect venue which is available on Saturday 24th June - which would mean my boyfriend's tourist visa would have expired by a few days already. We are afraid that might be an issue and that we won't be allowed to marry. (or even worse, that he might be arrested on the spot before the ceremony!!!). Also, would we have an issues when we apply for his family visa to remain in the UK with me? (I've been living and working in the UK for almost 17 years). We'd apply straightaway the Monday after the wedding.

Thank you!

You will encounter problems if you marry after your boyfriend's visa expires. The purpose of the Tourist visa is to visit and not marry. Additionally, the fact that your boyfriend overstayed his visa will be noted by the authorities.

Your boyfriend will not be allowed to apply for a visa whilst in the UK whilst here as a Tourist. He will have to leave the UK and re-apply for the appropriate visa.

Highly_Skilled wrote:You will encounter problems if you marry after your boyfriend's visa expires. The purpose of the Tourist visa is to visit and not marry. Additionally, the fact that your boyfriend overstayed his visa will be noted by the authorities.

Your boyfriend will not be allowed to apply for a visa whilst in the UK whilst here as a Tourist. He will have to leave the UK and re-apply for the appropriate visa.

A visa application isn't relevant as the OP is a dual Brazilian/Italian national. Once married it should be possible to apply for a Residence Card from within the UK as the family member of an EEA citizen. Depending of course on whether the sponsor is exercising her Treaty rights here.

https://www.gov.uk/apply-for-a-uk-residence-card

The HO will not appear at your wedding as they have told you they will not investigate your marriage, meaning they are convinced your relationship is genuine.
If your husband overstays before the marriage then he can still make application on Flr(fp) 10 years route.
He has the chance of getting the stay, if refused go for judicial review and you'll get it from court.

FLR(FP) isn't relevant here as I've already pointed out, the OP's boyfriend is applying under the EEA Regulations, not the UK Immigration Rules.