Where to start Although you can start on either end for your road trip, It’s best to drive south down the coast from Monterey so you can easily pull off of Highway 1 to take in the views. Definitely rent a convertible; being in the open air with nothing between you and the edge of the continent is worth the extra cost.
Where to stay Pismo Beach is a charming town and just a short drive from Morro Rock, where you can get your feet wet with some surfing (the waves and conditions are great for beginners). Book a room at the chicly beach-themed Inn at the Pier; this new oceanfront boutique property is comfortable and modern, perfect for a restorative night or two.
Where to eat Ventana Big Sur is worth the stop alone for the feeling that you are on the edge of the world as you dine high above the Pacific Ocean at The Sur House, not that the restaurant’s coastal cuisine (think crab salad and crispy oyster lettuce wraps) will leave you wanting for anything.
Where to drink In San Simeon, stop at the Hearst Ranch Winery tasting room, which is located in the historic Sebastian’s General Store, circa 1852. If you’ve timed your road trip well, schedule a tour of Hearst Castle (you’ll find it just across the highway from the tasting room) to explore this the grandeur of this historic estate.
What to see The graceful Bixby Bridge is one of the most photographed in Cali and worth admiring over from afar (or to make use of your drone if you’ve got one ). This architectural beauty is one of the tallest single-span concrete bridges in the world and it stands 280 tall over the majestic landscape of Big Sur. For a few hours of R&R, make it to Pfeiffer State Beach to kick back on its purple sand.