The Agonizing Joy Of Choosing A Holiday Watch

There’s a particular kind of madness that grips watch nerds before a big trip. Other people worry about airport transfers, currency exchange, or how many pairs of socks they need. I, however, have spent the last two weeks in what I can only describe as horological paralysis, staring at my watch box as if it were a chessboard. Soon, I’ll be flying from Australia to Europe for a month, bouncing between Italy, Greece, Slovenia, Austria, and the Netherlands. There will be swimming, pasta, and Aperol. And through it all, one watch — just one — will have to hang off my wrist every day.

And that’s where things get complicated. I’ve always loved the idea of a “travel watch” — something dependable, low-maintenance, and communicative enough to keep me entertained while waiting in airport lounges but anonymous enough that it doesn’t scream “rob me!” when I board a European metro system. Europe is notorious for pickpockets, particularly in certain places, and that’s not paranoia. This brings me to the central dilemma: when does a watch become too risky for holiday travel?

The perfect holiday watch? 

My default answer to everything involving water and adventure should now be my (new-to-me) Rolex Sea-Dweller 16600. It’s the ultimate dive watch — built like a submarine, water resistant to 1,220 meters, no nonsense, zero compromise. Every time I strap it on, I feel like I could headbutt a coral reef and come out on top. The Rolex Sea-Dweller is tactile and purposeful. It is truly my endgame dive watch.

And yet… picture me strolling through the streets of Barcelona, licking gelato, blissfully unaware of the pair of eyes watching for the glint of Rolex under a rolled-up linen sleeve. That’s the problem. The Sea-Dweller is too recognizable. It’s too flashy, despite its tool-watch humility. In Australia, it attracts little more than a nod from the occasional airport security agent. In Europe? It might as well be a neon sign that reads, “Mug me for resale value.” So, with a heavy heart, the Sea-Dweller cannot come. That left me with four other contenders for The Great European Watch-Off, each living in a different price bracket and offering a different philosophy of travel companionship.

Contender 1: Tudor Black Bay 58

My Tudor Black Bay 58 in blue is refined, understated, and impeccably built. At 39mm and on a soft NATO, it’s practically a holiday uniform unto itself. It has a sapphire crystal, a 200m depth rating, and that Kenissi caliber ticking away confidently like a well-bred butler.

But the Black Bay suffers from Rolex adjacency. Europe may not clock a Tudor instantly, but a polished case and Snowflake hands still carry luxury energy. If I’m wandering through Naples with a gelato in one hand and Google Maps in the other, I don’t want people scanning my wrist and thinking, “That guy’s got money.” I want them thinking, “That guy is confused and probably has no money.”

Contender 2: Seiko SKX173

This is where the conversation starts getting more democratic. The Seiko SKX173 is the kind of watch that is not ostentatious but does everything well. It’s the Americanized cousin of the classic SKX007 — same DNA, different hour markers. This Seiko diver was built to meet ISO standards, so it’s rugged. It’s the horological equivalent of wearing beat-up Converse sneakers: nobody thinks twice about it.

The Seiko SKX173 provided a lot of bang for the buck back in the day

The problem? I’ve already owned multiple SKX variants over the years. I love them like one loves a favorite T-shirt, but wearing one day after day for a month straight feels a little… unambitious. I want something with a bit more spark, something to reward me in quiet café moments when I sneak a glance at the dial between forkfuls of tiramisu.

Contender 3: Casio F-91W

Practically all watch nerds either own this or pretend they’ve transcended it. The Casio F-91W is the ultimate digital watch. It’s 20 grams of plastic magic. This Casio tells the time, and it beeps. It lights up with a glow reminiscent of old Nokia screens. From a security standpoint, it’s unbeatable. You could hold it out to a Parisian pickpocket, and he’d probably just pat you on the back sympathetically. I’ve showered with it. I’ve dived with it. It’s indestructible.

So, why not take it? Because I am weak. Because, for all my philosophical waxing about practicality, I like mechanical watches. I like seeing a seconds hand sweep rather than stutter. I like bezels that click, crowns that screw down, cases that carry weight. The F-91W is like eating toast for a month — satisfying enough but, ultimately, too monkish.

Contender 4: Seiko SRPL93 “Gene Kranz”

And finally, there’s the wild card. If you haven’t seen it yet, the Seiko SRPL93, dubbed the “Gene Kranz” after NASA’s legendary flight director, is a re-edition of an old 1970s Seiko 5 Sports diver. And, my word, Seiko nailed it! What I love about this watch is that it sits perfectly in the Goldilocks Zone of travel watches. This Seiko is mechanical. It’s water resistant to 100 meters — enough for the Mediterranean without inviting decompression stops. It’s visually interesting without being expensive.

Crucially, nobody is going to yank it off my wrist thinking it’s worth flipping, but I am going to catch myself smiling at it while waiting for airport espresso at 6:00 AM. For me, it ticks every box. After weeks of deliberation, I’ve made my decision. The Sea-Dweller stays home. The Tudor, too, is just a bit too luxurious. The SKX is too “tooly” for those fun evenings out, while the Casio is too austere.

The Seiko “Gene Kranz” is coming with me to Europe

This is not just the most sensible choice; it’s also the most honest one. As much as I love the idea of striding through Florence with a Rolex under a cuff, that fantasy collides hard with practical reality. Europe is beautiful, chaotic, and, in certain alleyways, opportunistic. A travel watch should make you feel free, not guarded. I don’t want to keep one hand over my wrist in busy plazas. I want to cannonball into the Adriatic without thinking twice.

The “Gene Kranz” gives me that freedom. It’s the kind of watch I can bash against a suitcase handle, rinse under a dodgy Airbnb tap, and still enjoy over gelato at midnight. The watch has enough vintage cues to give me just enough romanticism to feel like I’m traveling with intention. And if, along the way, I meet another watch enthusiast who recognizes it, well, then I’ll know I’ve found my people. So here I am, Seiko already on wrist, the Rolex Sea-Dweller tucked away gently in its box like a retired war hero. In truth, my dad will get to wear it for my trip away, but I might have trouble getting it back! Europe awaits. Gelato awaits. Excellent public transport awaits. But the wrist? The wrist is sorted. And that, fellow travelers, is half the battle.