The Best Rolex Watches To Wear On Vacation
The best watch to take on vacation is the one you already own. But if you own many, or you're in the market for a new one, it's fun to think about the ideal watch to take on holiday. I picked four Rolex watches and a Tudor that I think fit the bill, but I’d love to hear what watches you’re wearing on vacation this summer. Let us know in the comments.
One thing before I dive into the watches. The fun part about owning a nice watch is wearing it, but you always need to be aware of your surroundings and be willing to leave a watch at home if it’s the right move. Watch theft is real, and it happens more often when you're somewhere unfamiliar and not paying attention. I'm not trying to scare anyone off the idea of bringing their Rolex on vacation — just read the room. A little awareness goes a long way.
Rolex Explorer II
The Explorer II is functional for travel, comfortable, and flies under the radar more than a lot of other Rolex watches. The fixed 24-hour bezel and accompanying 24-hour hand was originally used by cave explorers to know whether it was day or night. But in the 1980s, Rolex introduced the caliber 3085, which allowed you to jump the local hour hand independent from the 24-hour hand. All of a sudden, the Explorer II could track two time zones and the GMT-Master II could track three. When you arrive in a new time zone on vacation, just jump the local hour hand to match. The 24-hr hand can track your home time zone or any other you prefer.
The Explorer II retails at $10,600 as of publishing, and it's one of the less-expensive, easier to attain steel sport Rolexes left in the catalog, which is part of the appeal too. If you want to go back a reference generation or two, you can save up to a few thousand dollars.
Tudor Monarch
This year's new Tudor Monarch is sort of the perfect vacation watch. In my hands-on with the Monarch, I described it as "a dress watch from the front and a sports watch from the side." You look at the dial and see 6 o'clock sub seconds, applied indices, skeletonized hands, roman numerals. You look at the polished case facets and bracelet with polished, peaked center links, also playing into the dress watch vibe. But then you pick the thing up and put it on — it’s a 40mm steel Tudor, screw-down crown (100 meters water resistant), full steel, Master Chronometer certification. You don’t have to baby the Monarch – it could easily be the only watch you bring on vacation.
The movement is the Master Chronometer MT5662-2U, certified by both COSC and METAS, with a 65-hour reserve, and for once Tudor lets you watch it run through a display caseback. It's $5,875.
Rolex GMT-Master II
Unlike the Explorer II, the GMT-Master II was designed with travel in mind. Same core idea and movement functionality — a second time zone — but here the 24-hour bezel rotates, so you can read a third zone on top of the two the hands already give you. It's the pilot's watch, and it's still the most travel-focused piece in the catalog.
The icon is the "Pepsi," with the red-and-blue bezel. Worth flagging if you're shopping: Rolex discontinued the steel ceramic Pepsi (ref. 126710BLRO) at Watches and Wonders in April 2026. Retail was $11,800. On the news the secondary market jumped — it peaked around $24,000 in May and has cooled to roughly $21,750 since, still close to double retail. If you want a GMT-Master II closer to retail, the "Batman" (blue and black) and the green "Sprite" are still in the lineup, and they're mechanically the same watch. The black-and-grey 126710GRNR is also a great choice.
Rolex Submariner
You knew a Submariner would be on here. The beautiful part about bringing a Submariner on vacation — you probably already wear it a lot. But vacation is where it thrives: 300m of water resistance, beefy steel construction, a watch you don't have to baby or think about. Any reference works. If you're taking an older one in the water, get it pressure-tested first.
'Two-Line' Rolex Submariner ref. 14060M
There are tons of Submariners to choose from. I can’t cover every single one here, but if I were in the market for a Submariner right now, I’d be looking at the ref. 14060M. This was the last 5-digit reference of the Submariner (without a date). So, this does not have a polished ceramic bezel insert, but a matte black aluminum one. It’s 40mm across with smaller lugs and crown guards than the modern 41mm Sub. It’s a bit more lowkey, and I really love the way it wears on my wrist. You can get them in nice condition under $10,000 all day, with some around $8,000.
Rolex Yacht-Master 42 in Titanium
In my hands-on with the titanium Yacht-Master 42, I called it my favorite modern Rolex. I still think that. Titanium makes it light enough that you forget you're wearing it, which goes a long way on a long travel day. It's water resistant up to 100m, and the bezel — black ceramic, sandblasted and polished — is the coolest in Rolex's current lineup, in my opinion. I love the darker, gunmetal look of this watch, the matte black dial, the big white indices.
The problem is buying one. MSRP is $15,250, it's one of the hardest Rolexes to get at retail, and the secondary market hovers around $25k - $30k+ depending on condition. Prices have steadily declined since the watch's release, however, even among broader Rolex market gains since early 2025. More on that in our recent pre-owned Rolex and Tudor article. But if you already have one, vacation is the time to wear it.
Final Thoughts
Those are my picks for a vacation watch in 2026, but like I said before, the best vacation watch is the one on your wrist. If you want the feeling of a new watch but don’t want to buy one, a high-quality strap is a great way to go. Try your Rolex on an integrated rubber strap from Everest; you can even use your Rolex’s OEM buckle to keep Glidelock and Easylink functionality. Alternatively, you can bundle an Everest strap with the new Everest Deployant Buckle, giving your bracelet a vacation of its own.
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