Yes, I make that decision every trip that I take. I been in Colombia, Puerto Rico, Dominican Republic, Venezuela and Brazil a few times and I'm always do my "Trip research" beforehand. It also helps when you have people that you know/family members in the country that you traveling to. They can tell you which spots are "safe" to walk around with your timepieces. But bottom line "streets smarts and a little common sense" is the key of every successful trip.
Last year blew up my 5% budget set aside for watches but it was a special lifetime occasion. I was retiring after 35 Years in the workforce. Spend over $15K including tax on this bad boy but how often you retire?
FYI, My wife wasn't very happy about it. 🙄
I usually bring a backpack carry on and I stuff my three watch roll in it. Usually I bring a G-shock, a dress watch and every day watch and the watch that I wear in the plane (usually my GMT). In total I travel with four watches. I select my timepieces depending of what I'm doing and how safe if the country that I'm traveling to. So far (knock on wood), it has worked for me and I been in 30 countries in five continents. Good luck on your trip.
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