Most Complicated Rolex Watches

rolex skydweller

The Most Complicated Rolex Watches:
Sky-Dweller, Yacht-Master II, and Cellini Moonphase

Rolex is most famous for its tool watches. Originally made for specific audiences, they each have a utilitarian purpose – the Submariner for diving, the Explorer for reading time in the dark, the GMT-Master for travelling. Rolex has always sought to make telling time easier in specific situations.

In the 2010s, Rolex came up with three watches that, some might say, are very much unlike their tool watches: the Rolex Sky-DwellerYacht-Master II, and Cellini Moonphase. They’re unusual, are priced much higher than their sport and tool watches, and are quite complicated.

While they’re the most complex watches Rolex has available today, they were also clearly made to be extremely practical. Here’s a simplified guide to each one.


Rolex Sky-Dweller: The Traveler’s Watch

Launched in 2012, the Rolex Sky-Dweller is a GMT watch and annual calendar in one. Of course, we know that Rolex has had the GMT function since the 1950s, but the annual calendar was unprecedented. It’s the first time that Rolex has featured a real complication, so to speak.


Rolex Sky-Dweller White Gold Black Dial Mens Watch
Rolex Sky-Dweller White Gold Black Dial Mens Watch
The Sky-Dweller resembles the Day-Date the most, with its case shape and fluted bezel. It comes in a very generous 42mm Oyster case, and has variations in Everose gold, and two-tone steel and white / yellow gold.


Rolex Sky-Dweller Yellow Gold Steel White Dial Watch
Rolex Sky-Dweller Yellow Gold Steel White Dial Watch
To read the Sky-Dweller, let’s dissect its different parts:


  • Center hour, minute, seconds hands – these tell the local time
  • 24-hour disc – this off-centered ring tells the hour in the second timezone. The red arrow above it is used as reference.
  • Month indicators – right above each hour marker are apertures that indicate the month. The box will appear to be color red to indicate the month. For example, the watch above has 11 o’clock marked, so the month indicated is November.
It’s worth noting that since the Rolex Sky-Dweller is an annual calendar, it will keep the month and date accurate without the need for adjustment – except on March 1st, to account for the difference in the number of days in February.


Rolex Yacht-Master II: Sailing Sophistication

When the Yacht-Master was introduced in 1992, it was created to be worn on the decks of a yacht. A top-shelf version of the Rolex Submariner, if you will.

Fast forward to 2010, Rolex unveiled the Yacht-Master II – this time, the watch is actually a tool watch for sailing and was developed to time the complicated countdown of a regatta race, as well as measure amounts of time spent at sea.


Rolex Yacht-Master II in different metal combinations
Rolex Yacht-Master II in different metal combinations
At 44mm, the Yacht-Master II is one of Rolex’s biggest watches (the other one being the Rolex Sea-Dweller Deepsea). It’s available in four different metal combinations, from lightest to heaviest: stainless steel, gold and steel, solid yellow gold, and platinum-white gold.


Rolex Yacht-Master II Regatta Chronograph White Gold Platinum Watch
Rolex Yacht-Master II Regatta Chronograph White Gold Platinum Watch
It’s easy to be overwhelmed by all the numbers on this watch. To read the Rolex Yacht-Master II, let’s dissect its parts:


  • Regatta chronograph – the blue contour in the middle of the dial is the regatta countdown timer, which works with the red countdown arrow in the center. In regatta races, sailors have to accurately measure the 10-minute countdown to the start of the race.
  • Ring Command Bezel – the bezel mirrors the regatta countdown timer. This is rotated counterclockwise to access, set, and then lock the programming of the 10-minute countdown chronograph.
  • Pushers – these are used to access the chronograph functions of the watch. Press the top pusher to start and stop the chronograph seconds hand. It will begin to sweep clockwise on the dial. Press the bottom pusher to reset the seconds hand back to 12 o’clock position.



Rolex Cellini Moonphase: Elegance and Nobility

The moonphase complication was last seen on a Rolex watch back in the 1950s. In 2017, Rolex brought it back on the Rolex Cellini, their line of traditional “tuxedo” dress watches.

In true Rolex fashion, this complication is not just beautiful ; it’s also very accurate that it will only need adjustment in the next 122 years.


Rolex Cellini Moonphase Everose Gold
Rolex Cellini Moonphase Everose Gold
The Rolex Cellini moonphase comes in a 39mm rose gold case. As a dress watch, waterproofness was not really a priority for this timepiece. It doesn’t come in an Oyster case and has only 50m water resistance.


Rolex Cellini Moonphase
Rolex Cellini Moonphase
To read the Rolex Cellini Moonphase:


  • Date – shown in the outermost track; used in conjuction with the thin, blued hands. This is controlled by an inconspicuous pusher on the case at 8 o’clock.
  • Lunar cycle – represented by the empty silver ring on the blue moonphase subdial
  • Full moon – the meteorite disc on the moonphase subdial






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