Fewer watches equals fewer headaches (ditto with toddlers). It’s easy to imagine all the different locations that will pop up during your fortnight in Torremolinos – a lounger, a nice restaurant, a high-stakes poker tournament, dinner on the yacht of an eccentric billionaire you bond with over negronis – and pick a watch for each. But versatility wins.

“I am less cautious personally than I would ever suggest to my clients,” says Ms Zoë Abelson, who posts her own knockout watches on @watchgirloffduty and sources them for others through Graal. “But I take two or three watches on vacation. Usually something that is more casual, something gold to match with my gold jewellery, and something that is a bit funky.”

As a rule of thumb, if you’re travelling for less than three days, take one watch. If it’s longer, maybe you need two. But if James Bond can wear a steel diving watch on the beach, at the baccarat table and for a shootout in a collapsing nuclear silo (your version: a trip to the local market), then so can you. Something like Oris’ Divers Sixty-Five or Chopard’s simpler Alpine Eagles work almost anywhere, worn with almost anything.

Other than timing eggs with your chronograph, it’s rare to really use most of the complications that watchmakers sweat over. Two of the best, however, are specifically designed for hopping longitudes.

GMTs and world timers track time in multiple time zones, normally where you are and where you just were. Holidays are the perfect excuse for one, even if it’s just so you know when the group chat is likely to be most amenable to your photos of sunsets. “I designed our Bamford London GMT with travel in mind,” says the brand’s founder, Mr George Bamford. He pairs his with “a titanium Aquaracer for beach holidays and the TAG Heuer Team Ikuzawa Carrera for evenings out.”

The big benefit of taking just one watch is that it need never leave your wrist, which is where it’s safest. If you do travel with multiples, make sure they’re close. “Always keep your watches in carry-on,” Abelson says. “Never put them in a checked bag.” This minimises the two things that can go wrong during the parts of a trip when you’re actually moving – theft and accidents.

Alertness and good insurance are your best defences, but a watch roll prevents any dings in transit. “A simple wrap,” Bamford says. “They’re an easy watch roll to take away.” His own watch roll is predictably sleek, or Lorenzo Milano’s lambskin leather version is even more slimline. Slot a GPS tracker inside – in case the worst does happen.

Chlorine corrodes gold alloys. Saltwater stains steel. And unless you’ve had your vintage diver pressure tested, that bar rating on its dial might as well be a pair of crossed fingers.

As mentioned, the best place for your watch is your wrist, and if your wrist is going to spend time near sun, sand, and sea (and, essential for you, but terrible for your timepiece, sunscreen), then your watch should either be robust enough to withstand them or affordable enough that you aren’t distraught if it’s not. And while a quick rinse and shine after the beach is always advisable, it kills the vibe somewhat if you’re late for dinner because you spent an hour battling all the icing sugar-like St Barts’ sand under your bezel.

The worst rarely happens, but better to assume it will. “Ask yourself what you feel comfortable travelling with,” Bamford says. “I wouldn’t take anything dainty or over-blinged. You want to wear these watches, but you have to be savvy about where you’re going.”

Though watch robberies remain rare, they are rising everywhere. In London, around of fifth of watch thefts now involve violence.

The best way to avoid being robbed is to make sure you’re not wearing anything worth robbing. If a watch is worth multiples of your destination’s per-capita GDP, maybe leave it at home. Avoid precious metals and brands everyone recognises (and knows the resale price of). That also goes for lookalikes. Counterintuitively, you’re more likely to be relieved of your gold Seiko Datejust than a bright and bold Club Campus.

Remember, too, that even the most comprehensive insurance has its limits. “There’s one watch I wouldn’t travel with,” Ableson says. “It’s a family heirloom from my great-grandfather. It’s absolutely irreplaceable and not worth the risk.”

Customs officials tend to be equal parts suspicious and ornery. When confronted with someone transporting multiple luxury watches across a border, they tend to assume you intend something more lucrative than taking multiple photographs of your wrist while holding a champagne flute.

When travelling in and out of the EU, for example, watches can be seized until you pay VAT on their full value. It’s reclaimable when you get home, but not easily. Some collectors have even been stung on both sides of a border – exiting a customs building is a solid hint that you’ve got something to declare.

If you must travel with multiple watches, pack receipts – better to prove their actual value than be at the whim of a Google-armed border guard armed – and don’t dissemble if officials do approach you. Declare your watches proactively and take the bureaucratic hit on the chin, rather than risk being charged with something more serious. You might lose them permanently.