How many watches do you take when you travel and how

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Only one, and if it's vintage, I also carry my weatherproof pouch in my pocket so I can quickly hide it if it rains or I need to wash my hands. Works well for spotty neighborhoods too.

But if I am going to the sea, I would just take my Seiko Monster and not baby it.
 
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I go back and forth on this question. I ALWAYS travel with my Apple Watch. It's on my wrist in the airports and if I'm working out. I'll frequently double-wrist if I think I'm going to need it. For instance, was pretty high up on my last outing - over 10K ft at times without a lot of time to acclimate, so i wanted to watch my O2. ( which was fine).

Usually I bring : 2 to 3 watches: 1. My Apple Watch; 2. Something mechanical for the flight usually set to the destination's timezone that I put on in-flight to help with jet-lag ( this really does help); 3. And if I"m bringing a third, it's because it fits the occasion in some way watch #2 won't always. Usually that third choice is a green Seamaster 300M since the green dial is so changeable in different lights. Or my strap-monster Panerai. Or a dress watch ( if either of those are watch #2 and I need a dressier piece). But on my last trip I brought my Speedy on the new bracelet w/the quick adjust. I was going to some patriotic sites in the west ( Mt. Rushmore, Yellowstone, Crazy Horse, etc. ) and I wanted to have it with me for reasons I can't exactly explain.
 
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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.