Making Our Way to Monterey in a 1939 SS Jaguar on California’s Fabled Highway 1
Highway 1 on the Central Coast of California is known as one of the most beautiful coastal roads in the world and is the ideal route for getting out on the road in your classic British car. We’ve been eager to make this drive for years, but for one reason or another, hadn’t gotten around to it…until now. For automobile aficionados, mid-August in Central California means Monterey Car Week—the largest and among the most prestigious vintage car events in the world. The destination—along with my recent acquisition of an original 1939 SS Jaguar 3½ Litre Saloon—made for the perfect opportunity to take a trip back in time up the coast to the holy grail of automobile gatherings.
It was a pretty great feeling hitting the road in a car of which only twenty-eight are known to exist. I knew there was a reason I drove nearly five-hundred miles overnight to race up and buy it only to turn right around and trailer back home. Making my way up this historic road with its majestic views was more than worth all the effort I went to acquiring the car.
We set off from San Luis Obispo, California at 7am and head north up Highway 1, passing through Morro Bay, Cayucos, Cambria, Harmony, and San Simeon—home of the legendary Hearst Castle once owned by William Randolph Hearst. Hearst Castle is open daily for tours, and if you look closely, can be seen from Highway 1 atop the eastern mountain range. If you’re lucky like we were, you’ll also catch a glimpse of zebras grassing along the property line. If you ever get the chance, take the night tour of Heart Castle—it’s quite a magical experience you won’t soon forget.
About an hour-and-a-half into the trip, we arrived at our first stop at Ragged Point where we settled in for breakfast at the Ragged Point Inn. The food and views from here are fantastic, making for the perfect spot for us and the SS to take a little break.
We were back on the road by 9:30 and ready to take on the winding costal road that is Highway 1. At this point, we had about ninety miles to go to reach the hallowed ground of Pebble Beach. Highway 1 is an absolutely breathtaking road with sheer drop-offs and gorgeous coastal views out one window, and the steep cliffs of the Santa Lucia Mountains out the other. Don’t spend too much time landscape gazing, though. This road is narrow and winding—so care should be taken attention paid to the posted speed limits. Navigating the road in the old SS Jaguar was a bit of a challenge with its mechanical brake system and heavy steering, but she was up for the task.
As we wound our way up, we stopped several times to take in the views of the gorgeous California coastline. Along the way are multiple bridge crossings and great photo opportunities where you simply have to pull over and capture with your camera. We were taking our time and really enjoying ourselves when we realized it was 12:30—time for lunch! We found ourselves in Big Sur, and after asking around, we decided we’d head to Nepenthe Restaurant for our midday meal. Nepenthe sits atop a hill and offers some of the most spectacular views of the coast I’ve ever seen. They are open for lunch and dinner and there’s an unimposing laid back feel about the place. The food is excellent and the menu features a wide variety of choices to satisfy everyone’s taste. You’d be hard pressed to find a better spot for a nice bite to eat. I can’t bring up Big Sur without mentioning the Bixby Creek Bridge, a concrete open-spandrel arch bridge that makes driving seem a bit like soaring as you roll along 280 feet above the surf. It’s one of the tallest single-span concrete bridges in the world and one of the most photographed bridges on the Pacific Coast.
We were back on the road at 2:00 and started making our way further north, making more occasional stops to bask in the stunning surroundings. One sight that really stood out was the Point Sur Lighthouse. It seems to pop up out of nowhere, perched on top of a large volcanic rock. Point Sur is a California state historic park periodically open for tours. If it had been open the day we were there, we would’ve certainly stopped and checked things out.
We only had about ten more miles to go before reaching our final destination, but they’re ten more extraordinarily picturesque miles. As we got closer to Pebble Beach, we passed through the quaint coastal town of Carmel which is known for its high-end restaurants and B&Bs as well as its sprawling coastal homes inhabited by the rich and famous. The closer we got to Pebble Beach, the bigger and more extravagant the homes got. We went from admiring the beautiful California coastline to now admiring and quite frankly, desiring some of these amazing residences.
Once we arrived, we headed right for the Lodge at Pebble Beach where we kicked back and relaxed at The Bench—a fantastic restaurant that overlooks the famous 18th hole and presents an amazing view of the bay. The fairway was buzzing as show personnel began setting up for the Concours de’Elegance.
The drive was simply awesome and we’d certainly do it again—but probably next time in a bit more modern British sports car! The car itself ran and drove flawlessly, but we were a little worn out from handling it the whole way. This drive would be nothing short of a blast in something along the lines of a sixties-era MG, Triumph, or Austin-Healey.
We can’t recommend this drive enough, but make sure to give yourself plenty of time to stop and enjoy all this legendary highway has to offer. And always remember to be safe and pay attention to speed limits and signs, as the road can get a bit dicey in spots. If you have any questions or are looking for recommendations, please feel free to leave a comment or shoot us an email and we’ll be glad to help.
Take a moment to browse the trip gallery to get an idea of what you’re in store for if you ever get a chance to take this wonderful ride.
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