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I need to go to Schengen zone and my flight back takes off at 11:30 PM. I need to specify the date of leaving Schengen zone and corresponding number of days in the zone in my visa application.
Do I specify exactly the day when the plane takes off or do I account for possible flight delay and specify the day after the plane takes off?
I recommend you to add one day to your application - there is no problem to stay one day less than you were going to, but you can get real problems if flight will be delayed - if you wouldn't pass through the customs in time, you can be marked into black list.
Three weeks ago I was on the train from Irkutsk (Russia) to Ulaanbaatar (Mongolia). A Canadian in my cabin had his visa finish on the 10th (same date as the departure of the train). Unfortunately it's a long train ride, and you don't actually cross the border the same day - meaning we crossed on the 11th, and as the border guard said solemly - "There is problem". He was fined 600 Rubels on the spot (about US$18) and had to pay an additional fine in Mongolia through the bank of 2000 Rubels (about $US60). The 600 Rubels apparently was a 'per day' thing - 10 days over would have been 6000 Rubels.
He was fortunate in that they didn't put anything in his passport or flag him in the system, as he would then have a black mark against his name from then on. A fine is bad enough. I'd personally try to put in as much extra time as permitted on the visa application (not sure how easy it is on Schengen to add days as I've not done it myself), but for example I met people who had a specified 12 day Russian visa, while you can just ask for the maximum of 30 and get it. Always worth going for the most.
(The closest I've come is taking a shared taxi out of Uzbekistan into Tajikistan with about 10 hours left on my visa. Also my toughest ever border crossing - arguing with a guy who has a machine gun is stressful!)
I think as in almost all visa applications it is not necessary to really cross the border at the specified date. It is only important do not enter before or leave after the date range. So I would specify the date the plane leaves.
Edit: Ok I saw you're leaving the zone. In this case, I would at least specify an extra date on your visa, so that you have some buffer if the plane is late or something like that. It is not a problem to leave the Schengen zone earlier than it is mentioned in the visa.
