Would it be safe to bring my Rolex to Europe (namely Greece and Portugal)? Or should I not?

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I would personally avoid. Stick to a cheap watch. I wouldn’t even wear Apple Watch in Greece

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I took my Diver with me to Greece and wore it in Athens, Mykonos and Santorini last year. Felt perfectly appropriate and safe on the islands. Athens was noticeably less safe due to the immigrants and I was a bit uncomfortable wearing it there.

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Having a watch insured is all well and good until you get stabbed by someone robbing you. It’s kind of a bummer, because I bought a Rolex GMT before the price craze and watch theft attention, for the purpose of wearing on those kinds of trips. But I’ll usually wear something else for international travel where I’m not super familiar with where I’m going.

I want to bring the watch on vacation but I don’t want to spend the whole vacation thinking about the watch on my wrist and trying to be conscious of what might happen to me or my fiancée. I wore an Oris to Italy in the fall - probably would have been fine with the GMT, but I’m glad I didn’t have to worry about it. Thieves are as good as you or me at spotting Rolex, Patek, AP, or other recognizable high-dollar watches - if you’re wearing something that doesn’t have the recognition then you’re probably fine.

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Love Americans who think everywhere else in the world is, like, something out of Mad Max or something.

Just like home, one must exercise good judgement. Some parts of town are fine, others maybe not.

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Even if it’s 90% safe and nothing bad will happen, it depends on what brings you peace of mind. I personally wouldn’t. Having to be extra conscious about it while on vacation doesn’t sound appealing to me.

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I mean I don’t think it would be any different than wearing it in a major US city.

I’m bringing my Rolex to Portugal, it’s not known for violent crime just pickpockets that with common sense you can avoid.

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I wore my Rolex in Portugal no issues at all. No safety concerns.

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