When I bought my genuine Day-Date new, I was stopped at customs six months later on my return journey from Italy back to Switzerland and they wanted a plausible explanation of where the watch had been bought. Fortunately, I was prepared and had a copy of the invoice in the glove compartment of my car....
The seller in Switzerland gave me this tip...
agreed.. people saying it won't happen have probably never traveled enough..
it's not just the new watch you bought.. i have a question: when you bought your rolex did they ask for your passport/id/etc?
i am convinced that the genuine articles are actually tied to travelers.. it's already in their systems so to speak
in dubai we went nuts on gold (why not, hello it's Dubai!) and were basically given paperwork on departure to get the "tax refund" back at the airport and then told to keep all receipts/etc just in case we got questioned
"Do you have anything to declare?" -- everyone gets asked this at customs.. and if you lie you're gonna get in more trouble cuz they probably already scanned your bag
..i know my heart skips every time i come back from the Philippines with a loaded checked-in bag of goods and knowing i have to go through customs -.- but no, for some reason if you do not declare "oh i have fake watches", you're fine.. remember, do you have anything to declare does not apply simply to fakes
good luck have fun!! where you going so we can get the bail money fund going?