Can I travel into the region on a Canadian passport, then use my U.K. passport on the way out?
When traveling with two passports, immigration will generally like to see your entrance stamp on the way out of a given country. So if you get stamped into a country on one passport and want to leave on another, you will sometimes be requested to show the entrance stamp that was put into the first passport.
Though your case is different than most people as far as the visa situation goes, as you are eligible for a UK passport. As you intend to have your new UK passport mailed to you subsequent to your arrival in the European Union on your Canadian passport, you will have no problems with staying anywhere in the EU for as long as you want. After you receive your UK passport, you will then have proof of being an EU citizen. This means that you can stay in Italy — or any other EU country — for as long as you please.
My recommendation is that you stay in Europe for as long as you want, and when you leave, simply show your UK passport. You should not be questioned, but if you are, just take out your Canadian passport, show the entrance stamp, and explain the situation.
When you receive the UK passport, you will have the full rights of an EU citizen, and should have no problems moving through immigration in the European Union.
As far as showing your passports to airlines and immigration at the airports, it is my impression that you can show either one to either party. Showing your passport to the airlines when you check is simply a matter of proving your identity, when showing your passport to immigration it is to make sure that you have an OK status to leave the country and be stamped out. If you are flying back home to Canada then it would probably be wise to show your Canadian passport to the airlines and the British passport to immigration.
I hope this helps. If you have any further questions, or feel as if this information should be updated, please comment below.
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Original question about traveling with more than one passport
Question about traveling with more than one passport:
I will be traveling to Greece this September on a Canadian passport. I will be staying in Greece for 90 days, then traveling to Italy for 2 weeks. This means that I will be overstaying in the Schengen area by 2 weeks.
However, I am also eligible for a U.K. passport. I won’t be able to get it before I leave (1 month) but I can get my family to mail it to me while I am in Greece. If I obtain my U.K. passport while I am in Greece, can I use it when leaving the country? That way, I could have my 90 days in Greece, then be eligible for another 90 days in Italy.
Basically I am asking if I can travel into the region on a Canadian passport, then use my U.K. passport on the way out. When I return to Canada, can I use the U.K. passport? And if I use it for the flight, does that mean I have to go through immigration on that passport? Or can I use my Canadian one…
Sorry if this is a bit confusing!