How many watches do you take when you travel and how

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Speedy with NATO strap, black leather and tan leather would get me through most occasions.
 
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Upon some Googling, first I am hearing of these two practices.

Do people "register" their watches with CBP upon leaving the US so as to not have them mistaken for new purchases upon re-entering? https://www.allgetaways.com/international-travel/declare-jewelry-watches-traveling.html

And do people ever declare their watches for personal use upon entering foreign countries so as to not have them mistaken for items being brought in for commercial sale? https://quillandpad.com/2023/05/21/...g-but-heres-how-to-avoid-the-worst-reprise-3/

How common are horror stories of having to pay erroneously for persona, already-owned watches worn into foreign countries or back into their home countries?!
 
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Upon some Googling, first I am hearing of these two practices.

Do people "register" their watches with CBP upon leaving the US so as to not have them mistaken for new purchases upon re-entering? https://www.allgetaways.com/international-travel/declare-jewelry-watches-traveling.html

And do people ever declare their watches for personal use upon entering foreign countries so as to not have them mistaken for items being brought in for commercial sale? https://quillandpad.com/2023/05/21/...g-but-heres-how-to-avoid-the-worst-reprise-3/

How common are horror stories of having to pay erroneously for persona, already-owned watches worn into foreign countries or back into their home countries?!

There was that horror show when Swiss customs charged people who were attending Baselworld a couple of years ago, but for three years I used to travel over 90,000 miles a year for work -- Asia, Europe, US -- never had less than 5 watches on me and never had a problem. I've also immigrated with my entire collection a couple of times: customs in Australia showed a bit of interest, but didn't charge me anything.
 
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I've never been stopped by any customs people anywhere who were interested in any of my watches. They have bigger problems to chase, ie drugs and cash. US has totally dialled back its customs presence, no more forms to fill out while on the plane and the red lane/green lane arrangement is mostly gone, in fact you'll be hard pressed to often find an agent. In the US at least they believe that chasing duty from travellers is a non-productive exercise, it's been that way for years. Other countries, not so much.
 
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I used to travel with dozens of watches in my ignorant youth. What seemed to cause trouble was music boxes.

A steel studded brass cylinder filled with organic material. Sets off the detector every time.

I once got pulled into the "room" carrying an uncased Violin back from Vienna in my book bag. Was cheaper than the little miniature souvenir toys. Bought a bunch of clocks too. Those were in the checked in the luggage.

My Uncle worked for the Airlines, then after retirement worked for Customs. He told me to just put the stuff in a cardboard box what fit under the seat. Or checked through.

One time the pilot asked me if I had donuts in the cardboard box. Now I wonder if that was Mad Dog?

The box was actually full of organ pipes.
 
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Just got back from an Alaskan cruise, only took my new White Dial Speedie. Would of felt comfortable packing a couple if it was direct on the ship and back home after debarkation, but with staying before and after in Vancouver/Seattle, didn't want to worry about another thing. Started on my wrist and every time I was out the room, so was it. Made life easier and it dressed up and did casual great as well.
 
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When flying, I usually wear my smart Apple watch for convenience and notifications. For the trip, I typically bring 1-2 luxury watches based on the events I’ll attend. It's a good idea to store them in a secure travel case in your carry-on to keep them safe. And if you're flying business class, you'll have a bit more space and comfort to manage your belongings during the flight.
Edited:
 
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if you bring two, do you ever wear your second watch on your wrist while in transit on the plane?
 
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I just bring one, I like the idea of picking one to accompany me. If I was concerned about theft, I'd bring a cheap one.
 
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No work meetings on this trip, just good food, music and sporty things. So just one watch…

 
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2 cheapish watches
 
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I leave with one when I go internationally, but I seem to return with two many times.
 
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Primarily, 1960 steel Constellation, piepan, no date. Anywhere from casual to semi dressy.

If the trip will include astronomy activities, also a Casio dual time, with one time set to UTC. Red LED display for minimal disruption to dark adaption.
 
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2 of my favourite Seiko. Not flashy but reliable
7A28 Gen 1 Chrono
SPB147 Diver
 
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I take 1 watch, on my wrist. It is usually the cheapest watch I have.
 
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I’ve traveled with multiple watches and have cases/envelopes for protection. In the end, I stick to one watch. The stress of leaving one out of my control in a strange place is not worth the options
 
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I always take two watches with me. My iwc and my samsung smartwatch. I take them straight up in my bag. No protection at all. Living on the edge. Although I did want to bring one of my kontiki's. But my girlfriend said that they are'nt waterproof. So of course I listened to her
 
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My current shortlist for a city break in Scandinavia later in the summer.

I imagine I’ll wear one and take one or two of the others.