Photo Report: Experiencing Car Week Through The Lens Of Rolex

Welcome to Car Week, an annual event held in August that sees the automotive world descend upon the Carmel-Monterey area for a series of shows, events, unveilings, and more – all leading up to the Pebble Beach Concours d'Elegance on Sunday. This past weekend, I attended the main events during the latter portion of the week with Rolex. The famed Swiss brand has been a long-time supporter of a handful of events, and the four days I spent in the area included no small measure of amazing cars, along with an endless stream of Rolex spotting along the way.

For this Photo Report, tag along with me as we go inside four of the week's highest-profile events to get a closer look at what makes Car Week one of the biggest automotive gatherings in the world. From the Tour D'Elegance to vintage racing at Laguna Seca, and even an extra-special Rolex awarded to the Best of Show winner at the main event on Sunday – if you're a car enthusiast (or even just car-curious), it's a genuinely special experience.

Fair warning: you may want to warm up your scrolling finger before getting started; it's a whole lot of images…

Day 1 – The Pebble Beach Tour D’Elegance

While this was my third time attending various elements of Car Week, I have never experienced the Pebble Beach Tour D'Elegance. This year, my adventure kicked off with the tour, and the idea is that it's a public event that allows a closer experience with 150+ of the cars that will be featured on Sunday at the Concours. Those willing to find parking can grab a donut and stroll around the various cars before the tour rolls out on the 70-mile route that primarily features a long cruise down Highway 1 to Big Sur and then back to the lodge at Pebble Beach.

If you want to see the cars, especially if you want to see them moving (which is quite spectacular), this is arguably the only accessibly priced option because the Tour is free. Rolex has been the main partner for the tour since 2007, and it's no small event. All along the route from 17-Mile Drive to Highway 1, the roadside is lined with waving spectators, photographers, and no shortage of—you guessed it—great cars.

With my camera in hand, I spent some time roaming the long line of cars before getting a chance to actually ride along with one of the entrants – a 1940 Derrin-bodied Packard. This car is actually the first-ever Derrin-bodied Packard, and with its smooth performance and drop-top layout, it's hard to imagine a sweeter way to enjoy the tour, the cars, and the incredible scenery.

I love the smell of coffee, donuts, and 1966 Ford GT40 XGT-2 MKIIs in the morning.

A stunning 1967 Ferrari 275 GTB/4 Berlinetta.

A modern 43mm Rolex Sea-Dweller 126600.

The headlamp of a Porsche 356.

Not hard to see how the (1960) Maserati Tipo 61 "Birdcage" got its name.

The Birdcage from another angle.

It's not all mid-century classics; check out this truly amazing 1988 Cizeta-Moroder V16T Prototype. What a thing.

A 1934 Bugatti Type 59 Sports, which would go on to win Best of Show a few days later at the Pebble Beach Concours D'Elegance.

The lovely badge work on a 1967 Bizzarrini 5300 GT Strada Series 1 Coupe.

A 1958 Ferrari 250 GT Pinin Farina Cabriolet Series 1.

The nose of a well-worn 1965 Serenissima 308V Fantuzzi Spyder.

The hood ornament of a 199 Packard 1708 Twelve Derham Sport Phaeton.

The charming interior of a 1953 Nardi 750 Frua Barchetta.

A simply gorgeous 1965 Maserati A6GCS Frua Spyder.

A 1960 Porsche 356B 1600GS Carrera GTL Abarth Coupe.

Waiting for traffic in a 1929 OM Tipo 665 SSMM Sport Milano Team Car.

Two entirely different futures, a 1960 Plymouth XNR Ghia Roadster alongside the 1988 Cizeta-Moroder V16T.

Part of the Land Rover HM Queen Elizabeth II exhibition, a darling 1954 Land Rover Series 1 86" Soft Top.

The Series 1 is flanked by something a bit more modern from her stable of Land Rovers.

Details on a 1960 Aston Martin DB4GT.

The interior (if you can call it that) of a beautiful 1907 Packard 30 Runabout – 117 years old!

A closer shot of the 1907 Packard 30 Runabout's 8-day dash clock, which includes a monogram.

A 1953 OSCA MT4 Fura Spyder. Just think, you could have been driving this with the first-ever Rolex Submariner on your wrist back in '53.

Not all tour attendees are created equal.

A Rolex Daytona 116508.

We took to the route, and I got to take in the views from the backseat of a 1940 Packard 1806 Custom Super Eight Darrin Convertible Victoria (the first-ever Darrin-bodied Packard). What a ride and one hell of a hat.

Eager crowds wait at the roadside at Monastery Beach to catch the tour en route to Big Sur.

My own trusty Explorer II 16570.

Tour onlookers climb small hills to get a better view of the passing cars.

After turning around in Big Sur, the cars behind us started to fly by. Here, we get a rare view of the 1970 Mercedes-Benz C111.II.

One of my favs from the entire event, a 1962 Land Rover 109 Series IIA Special Station Wagon rolls by on Highway 1.

Here's a rare sight: a 1954 Jaguar D-Type Prototype (one of my all-time favorite cars), followed by a 199 Vector W8 Coupe.

An incredibly gorgeous 1954 Lagonda V12 Race Car owned by Lawrence Stroll. This is DP115/2, but don't worry. Mr. Stroll also brought DP115/3 – I'll show you in a bit.

A 1958 Porsche 356A Speedster.

Roadside photographers finding a way to get the shot.

Blink, and you'll miss this 1962 Ferrari 400 Superamerica Pininfarina Coupe as it goes by.

Not your usual traffic jam on Highway 1 as multiple hypercars from Pagani, McLaren, and Bugatti wait for a single-lane crossing on the bridge.

The 1965 Serenissima 308V Fantuzzi Spyder drives by.

A Rolex GMT-Master II 126710BLNR.

To close out the day, here is a better look at my ride for the tour: a 1940 Packard 1806 Custom Super Eight Darrin Convertible Victoria.

Day 2 – The Quail

Fighting the start of a fresh sunburn, my Friday was focused on a single event: The Quail. In what some have called, in jest, the Catalina Wine Mixer of Car Week, The Quail is essentially a cross between a garden party and a full-on car show. There is food, drink, brand-driven product unveilings, and a collection of cars that includes Carrol Shelby-driven MGs to modern hypercars, restomods, boutique brands, and even displays from major manufacturers like Porsche, which had a huge collection of 911 Turbo models to celebrate the 50th anniversary of the Turbo.

The event lasts for much of the day and is held at the Quail Lodge and Golf Club under the direction of co-founder Gordon McCall. The show was originally launched in 2003, and Rolex has been involved with the event since 2005 and this year's programming included some special testimonee names on the guest list, including legendary racer Hurley Haywood (also a legendary Talking Watches guest) and 2009 F1 Champion Jenson Button.

It's a sunny, shiny, and endlessly swanky event that offers an abundance of beautiful cars and no shortage of Rolex (including some common and some more uncommon models).

Dressing up a Rolex GMT-Master II, this is the wrist of photographer Tom O'Neal. He was shooting for Rolex but is well known for his incredible work, which includes many famous photos of rock stars such as Joni Mitchell, CSNY, and The Rolling Stones. He also has a couple of images at the end of this story.

It's not The Quail without him.

The headlamp of a Meyers Manx. I love these so much.

The Porsche 911 Turbo 50 Years celebrates, well, you get it.

A classic 930 Turbo with some excellent graphics.

A Rolex Explorer.

The many cowboy hats seen in the crowd were supplied by Ruf in connection to their new Rodeo model.

Love the interior.

An Everose Rolex Sky-Dweller 336935.

A platinum 126506 Rolex Daytona in the modern spec with diamond markers.

Race car driver (and Talking Watches alum) Hurley Haywood wearing his 126710BLRO GMT-Master II.

Never mad at seeing a Citroen DS.

The raucous new Gunther Werks GWR.

Evan Orensten of Cool Hunting with a darling Rolex Air-King with a custom dial.

A Rolex GMT-Master II 16710 "Pepsi."

A 1958 Ferrari Testa Rossa.

The new Aston Martin Valkyrie.

A 16570 Explorer 11, and it's not mine!

A more common sight at The Quail, a Rolex Daytona (reference 116500).

The headlight on the GMA T.50.

The three-seater interior of the GMA T.50.

One of my fav cars at The Quail, the Tuthill 911K. It revs to 11,000.

His and hers, but make it Rolex.

Nice to see the vintage side represented by this lovely Rolex Daytona 6363 "Big Red."

Adrienne Faurote of Haute Time strolls past Magnus Walker's 911 Turbo.

Can't believe I actually saw a Rolex Deepsea Challenge in the wild (I mean, the wild of The Quail). It wasn't actually hard to see, either, as it's 50mm wide.

My kingdom for an Aston Martin Valour. Green carbon is a-ok, I'm not picky.

A two-tone Rolex Datejust fits in nicely at The Quail.

Visions of F40.

F1 Champion Jenson Button's Rolex Daytona 116508.

F1 Champ and Rolex Testimonee Jenson Button.

Note the background Alfa in its natural habitat (sorry Thomas).

One of my fav references, the Rolex Submariner 14060M.

A 1953 Ferrari 250 Europa Vignale.

Another Rolex Daytona 6263, only at The Quail.

Vanquish. Yellow.

Magnus Walker's 1977 Porsche 911 930 Turbo.

Seen on Paul Zuckerman's wrist, the iconic Daytona "Paul Newman" 6241. This was at a hotel, not The Quail, but I had to share.

Ferrari field.

Gordon McCall, co-founder of The Quail, wearing a Rolex Submariner 16610.

The lovely and minimal dashboard of a Porsche 356.

Another Paul Zuckerman sighting, this time sporting a lovely gilt dial 5513 Submariner.

Amazing color for this Ferrari Dino 246 GT.

A two-tone Rolex Daytona 116523.

The final version of the Pagani Zonda, the Zonda 140 Arrivederci. I have such a fondness for the early versions of the Zonda.

The Tuthill GT One was debuted at The Quail.

The solid yellow gold reference 228238 Rolex Day-Date 40.

Day 3 – Rolex Monterey Motorsports Reunion

The main event for my penultimate day of Monterey Car Week was Saturday's Rolex Monterey Motorsports Reunion. The event runs for several days and brings a huge variety of race cars and would-be racers to WeatherTech Raceway Laguna Seca, but Saturday is the big day, and – in the event you're not tracking a theme here – Rolex is the title sponsor for the event, and Jenson Button was competing in his truly gorgeous 1952 Jaguar C-Type that was previously owned by racing legend and Formula 1 Champion Juan Manuel Fangio.

A vintage Formula 1 car once driven by Niki Lauda takes to Laguna Seca raceway.

Of the four main events I attended, this bright and clear Saturday at Laguna Seca is the peak for me. The entire infield is largely open to attendees, and you can walk past the make-shift pits to see the cars being prepped, get a hotdog and watch the cars slide around turn 3, or climb the hill to watch the cars slither through "The Corkscrew," Laguna Seca's legendary turn 8 corner that is almost impossibly steep and difficult to judge for newcomers to the track.

Much of the racing features beloved retired racecars coming to the track for a rare lap and some wheel-to-wheel racing. For our afternoon, we got the chance to hang out at the top of The Corkscrew with Hurley Haywood for the running of the Hurley Haywood Trophy Series, which features a selection of cars from 1981-1991 and spans several series including Group C, GTO, and Trans Am. A personal highlight for me was the chance to see the jaw-droppingly cool Group C Mazda 767B. As a Gran Turismo kid, it's hard to explain just how cool it was to see that green and orange livery rolling through The Corkscrew.

A Rolex Daytona 126518LN.

The legendary 1989 Mazda 767B (002) dives down The Corkscrew at Laguna Seca.

A Meyers Manx in the wild.

Rolex Testimonee and F1 Champ Jenson Button swapped his yellow gold Daytona for a white gold "Le Mans" 126529LN Daytona. It's a fitting choice for race day.

My pal Franco sporting his Rolex Milgauss 116400GV.

Cameron Barr of Craft & Tailored sporting a Rolex Submariner 1680.

JPS!

Hurley again. Just a cool shot of a cool guy.

A Rolex Daytona 126500LN.

One final shot of the 767B heading down into 8A on The Corkscrew.

Day 4 – The Pebble Beach Concours D’Elegance

The main event. The Pebble Beach Concours D'Elegance was first run in 1950 as a side event for the Pebble Beach Road Races. Now in its 73rd year, this prestigious judged competition has had Rolex as a partner since 1997. This year, more than 200 cars from all over the world showed up to compete both in specific classes and for the illustrious "Best of Show" award.

This year, the Best of Show winner also received a special version of the Rolex Perpetual 1908 in yellow gold with a brown leather strap that has a Rolex green lining and connects to a deployant buckle, which is engraved with the event's logo and "Best in Show 2024." Given the 1908's display case back, Rolex had to get creative with the engraving, and it's a watch that certainly meets the profile and vibe of this annual event.

The Rolex Perpetual 1908 that was awarded to the Best of Show winner for the Pebble Beach Concours D'Elegance.

The special engraved clasp...

The Rolex 1908 and the trophy for Best of Show (Rolex/Tom O'Neal).

I went to bed (slightly) early the night before so that I could take part in "dawn patrol," which gives show attendees a chance to rock up early and see the cars driven onto the lawn at Pebble Beach. No, I wasn't early enough or lucky enough for one of the hats, but it was amazing to watch the cars drive onto the grass and slowly get placed for the day's show.

The Best in Show award went to a spectacular and wholly unrestored 1934 Bugatti Type 59 Sports (featured at the end) that is part of The Pearl Collection, which is based in Zug, Switzerland.

Phillip Sarofim's one-of-one 1979 Aston Bulldog will be familiar to many of you...

A jaw-droppingly cool 1957 Maserati 450S Spyder.

McLaren F1s are always a treat to see.

A delightful old Packard rolling onto the fairway.

A 1973 Ferrari 365 GTB/4 Scaglietti Competizione Berlinetta.

Appropriate footwear.

Appropriate wrist wear.

A 1996 Ferrari F40 GTE Michelotto – with F.A.T. logos.

One of the most spectacular cars at the show, this 1971 Rolls Royce Phantom Vi Frua All-Weather Cabriolet. It's the last Phantom VI ever made and was a 1993 Geneva Motor Show car (which was when the car was completed).

I've seen less-equipped bars on Smith Street in Brooklyn. Shout out Wing Bar.

Controls.

Tea tray details.

Heck of an office, if you can get it.

A 1953 Aston Martin DB3S Race Car.

Dash details.

The first 126718GRNR GMT-Master II I've seen since Watches & Wonders.

A row of Maseratis.

A 1966 Ford GT40 XGT-2 MKIIs.

A Rolex Oyster Perpetual 36 116034.

A 1954 Lagonda V12 Race Car

The interior of a vintage Lagonda V12 race car.

Another 1954 Lagonda V12 Race Car.

A gorgeous 1956 Fiat V8 Zagato Berlinetta.

A 1962 Land Rover 109 Series IIA Special Station Wagon.

Check the passengers.

My favorite car at the show, a 1955 Jaguar D-Type Le Mans Race Car.

Details on the 1955 Jaguar D-Type.

My friend Nicholas Kalikow with a killer vintage Day-Date 1803.

One of the higher-profile cars at the event, a 1962 Ferrari 250 GTO that was recently restored by Ferrari Classiche.

And the back.

A modern Rolex Submariner 126610.

Love to see a Rolex Submariner "Hulk" 116610LV in the wild.

Automotive editor Bob Sorokanich getting the shot (and lots of compliments).

A closer look at the 1973 Ferrari 365 GTB/4 Scaglietti Competizione Berlinetta.

Jaeger clock faces on a 1954 Lagonda V12 Race Car.

Matt Farah (of The Smoking Tire) pairing Rolex with his wife, Hanna.

Another look at Matt's Submariner "Kermit" 16610LV.

The scene as the crowd awaits the award ceremony for Best in Show.

The dashboard details of a stunning 1948 Talbot-Lago T26 GS Saoutchik Fastback Coupe.

A very rare treat to see one of the darlings of Watches & Wonders 2023, a 36mm "Emoji Puzzle" reference 128239-0056.

The Lancia Stratos HF Zero Bertone Coupe waiting on the lawn.

A Polaroid Porsche from Galpin.

Here's another rare one, a Rolex GMT-Master II 11675SARU – check out those lugs.

Yet another special treat (and a model I've never seen in real life), a 34mm Rolex Oyster Perpetual Datejust Pearlmaster with a fully set dial and bezel.