The Best Rolex Watches To Wear On Vacation

The first thought you probably had seeing this title: “The best Rolex to take on vacation is the one already on my wrist.” You’re not wrong. But there are some Rolex models that feel particularly at home while relaxing by a pool, exploring a new city, or swimming in tropical waters. Here’s a rundown of a few watches that pair especially well with vacation vibes.

Rolex Celebration Dial Oyster Perpetual

Image Source: Bob's Watches

Wearing a Celebration Dial OP is practically a vacation in and of itself. With a dial full of vibrant-colored bubbles, it’s the horological equivalent of a Hawaiian shirt—bold, playful, and exactly the kind of watch that should be peeking out from your sleeve when holding a cocktail.

Curved-End Rubber Strap For Rolex Oyster Perpetual

But if the Celebration Dial is too busy for you (or simply impossible to source), any of the colorful OP dials—turquoise, coral red, candy pink, or the new pistachio—will deliver that carefree, vacation-friendly look. Plus, the rugged Oyster case (with 100m of water resistance) and straightforward design means this Rolex can handle some swimming and even recreational diving. Want to add even more practicality? Throw it on a curved-end Everest rubber strap—no bracelet scratches, and a lightweight, comfortable feel in hot weather.

Rolex Submariner

Image Source: Hodinkee

Picking a Submariner as a vacation watch might seem obvious, but clichés are usually clichés for a reason. The Sub isn’t just iconic—it’s ideal for travel. Few watches transition so well from 20 meters underwater to a Michelin-star dinner. The lume on a Submariner, charged by long days in bright sun, feels extra strong on warm vacation evenings—especially when you step out of the blazing heat into a cool, dim hotel lobby.

Curved-End Rubber Strap For Rolex Submariner

And no, you don’t have to dive with it, but the knowledge that you can (with any generation, provided you’ve pressure-tested an older reference) somehow makes beach days a little more fun. It’s also incredibly strap-versatile: a tailored Everest rubber strap for swimming, leather for evenings out, or just stick to the Oyster bracelet—it all works.

Rolex GMT-Master II

If your vacation involves getting on a plane, you should probably be wearing a GMT-Master II. Yes, your phone tells time zones perfectly well, but setting that GMT hand forward as your plane crosses international borders remains uniquely satisfying (especially with the jumping local-hour hand).

Like the Submariner, the GMT-Master II offers an ideal blend of tool-watch toughness and everyday luxury—particularly in stainless steel. Whether your favorite flavor is a classic Pepsi, Batman, or the more subtle grey-and-black GRNR, it’s a natural travel companion: comfortable, capable, and sharp enough for dinners out. And if you’re traveling with your Rolex, Everest’s watch rolls and travel pouches offer peace of mind and padded protection in your carry-on.

Rolex Yacht-Master 40

Curved-End Rubber Strap For Rolex Yacht-Master

Some Rolex models just feel inherently summery, and the Yacht-Master 40 is undeniably one of them. It’s slightly more upscale in its finishing and detailing compared to other sports models, without sacrificing the go-anywhere flexibility you want on vacation. The dramatic curve on the lugs makes for a wrist hug like no other. The bezel—whether platinum or gold—is just the right amount of flashy. The YM40 looks particularly good on a rubber strap, leaning into its nautical heritage. (If you somehow snagged a titanium Yacht-Master 42, it might be the ultimate subtle flex for vacation.)

Rolex Yacht-Master II ref. 116680

Image Source: Monochrome Watches

This one might surprise a few people, but the steel Yacht-Master II makes a strong case as a vacation watch—if not on paper, then definitely on the wrist. Yes, it’s big (44mm). Yes, the regatta countdown complication is wildly specific. But this watch is fun—which is exactly what you should be having on vacation.

What makes the Yacht-Master II so enjoyable in this context is that it doesn’t pretend to be low-key. The dial layout is unlike anything else in Rolex’s lineup, the Ring Command bezel feels like a party trick, and the overall wrist presence is hard to ignore—in the best way. I know people who own, wear, and love this watch.

Image Source: The Watch Club

And frankly, it’s a good time to buy one. We just covered this watch in our latest pre-owned value piece—prices are significantly down from retail, and if you’ve been on the fence, it might finally make sense to go for it.

Final Thoughts

A vacation watch shouldn’t just survive the trip—it should add to it. All five of these models bring something different to the table, and with the right strap swap (rubber for the beach, leather for dinner), you can keep your setup light and your bracelet safe. If you’re taking your Rolex abroad, check out our guide to safely traveling with a Rolex—it covers smart, low-profile ways to keep your watch secure on the go.