If you are still reading this, I will leave it to others to hector you on the legality and/or morality of what you are doing. But, as I have posted before, if your goal is to enter the Schengen area with as few questions as possible, I recommend entering via Copenhagen, as the immigration checks there are quite limited.

Avoid entry via Switzerland, at all costs.

Is this of help to answer questions?
http://europa.eu/legislation_summari.../l33139_en.htm
Airlines will be fined so they do check.

Here is the epilogue if anyone is still out there, and if my story is helpful to anyone in the future:

Thanks to every for your input and replies. My summary of most of your replies goes a little something like this, "Let me get this straight. You broke the law and were lucky enough to get out alive the first time. Now you are stupid enough to dare break the law again? Not only that but you brought innocent children into this lawless situation. You should be ashamed Of yourself. Get your family out immediately if not sooner and certainly don't make it worse by going back."

And I don't disagree...

In the end, after all of that, I decided to fly through Rome and take my chance with the Italian passport control. It wasn't a great plan, but it was the best of a limited number of other bad options. When I got to Rome, the officer flipped open my passport and handed back to me in about 37 nanoseconds. He could not have cared less or looked at it for less time. YMMV and please don't try this at home.

Thanks again for all of you that gave me your serious thoughts and suggestions. It helped!

Looks like a win for J62. With five years of interest.

When I went through Bergamo Airport in June, the border agent looked carefully at my British passport, studied various stamps I have collected, put it trough a scanner and compared against Schengen database, and asked me where I was heading for. This is a big change from my previous experiences in Italy where they barely looked at the passport before tossing it back. So there is definitely a heightened security and greater scrutiny of documents.

So, are you and the family traveling again for another month?

>>So, are you and the family traveling again for another month?<<

They traveled 5 years ago -- he likely wouldn't get away w/ that now.

Janisj, you are right. Didn't notice that when it was the OP, himself, who brought it back up after 5 years. That in itself is pretty funny.

In any case, Bill, thank you for bringing us up to date, even if a bit belatedly. So very glad you got you and your family away safely!

I'm sure things have changed and everything is now on some monster EU database that would snap you up instantly if you tried that today.

Recently border staff are known to count the 90 days from passport stamps to check compliance with Schengen rules. This is more likely in 'fussy' countries like Switzerland, Germany, Netherlands and Poland, but in the current security climate, just about anywhere in Schengen area.

Also UK border force are known to deny entry to those who have broken Schengen rules, from passport stamps, even though UK isn't part of it. The reasoning is that someone who breaks another jurisdiction's immigration rules can't be trusted not to do the same while in UK. Immigration officer is empowered to deny entry to someone on whom they have a reasonable suspicion that they may break the law.

Even though this is and old post I will post my view. Alec. Not only in the UK but here in Australia as well. Life has changed dramatically since 2011 and if you overstay in one country it shows that you are prepared to not comply with laws and as mentioned by nukesafe you would be entered on to a list fined, and face an exclusion period of up to five years.
The complete disregard of another countries laws is mind boggling let alone the example set by a parent. Shame on Bill.

He made the effort to come back 5 years later to let us know (brag) he got away w/ it.

let's see. I put in my 2c, and at 10:1 odds that 2c = 20c total. Add in 5yrs interest at 2.45% that rounds off to a whole $0.25. I won't spend it all in one place.

If only I'd been so luck at the track on Saturday for the big race - an 11:1 long shot pulled off the upset and set a new stakes/track record!