The California Road Trip Every Founder Should Take Before She Burns Out
A four-day Highway 1 escape filled with good food, great wine, unexpected adventures, and plenty of room to simply be.
When your calendar has been running your life for months, the last thing you need is another vacation packed with standard sightseeing. This four-day California Central Coast road trip on Highway 1 is built around permission to slow down, something entrepreneurs rarely give themselves.
From watching elephant seals along the coast to soaking in hillside mineral springs, riding a Clydesdale through the hills, foraging for seaweed, and lingering over long lunches at local restaurants, every stop invites you to trade productivity for presence. More importantly, it gives you permission to leave “white space” in the schedule. Versus back home, where color-coded time blocks on the calendar rule each day.
Southern California founders can drive up from San Diego, Los Angeles, or Santa Barbara to San Simeon. Others can fly into LAX and make the 3.5-hour drive to San Simeon to begin the journey.
Day One: Start With the Wild Coast
Begin your trip around San Simeon, where the pristine, almost dreamlike coastline immediately signals this isn't a typical California getaway. Stop at the Elephant Seal Rookery to watch hundreds of elephant seals lounging on the beach. If you're lucky, you may also spot whales breaching offshore as we did on our most recent trip.
Then continue north to Ragged Point, considered the “Million Dollar View” gateway to Big Sur, and your first overnight. Perched 350 feet above the Pacific, Ragged Point Inn feels appropriately “rugged” for this stretch of coastline. The property offers simple, spartan ocean-view rooms and direct access to nearby coastal hikes.
Word to the wise, do NOT take the Ragged Point Cliffside Trail on the property unless you’re in the mood for some broken bones, as the front desk staffer told us! The trail drops down the 350-foot cliff toward a black sand beach, with views of the Pacific and Santa Lucia Mountains along the way. Easier coastal hikes nearby are a bit safer.
For dinner, stay put. The Ragged Point Restaurant serves simple cuisine and local wine (at incredible prices) from its glass-enclosed dining room and outdoor deck overlooking the cliffs. Sunset is the obvious move.
Then do something that may feel uncomfortable for a founder: absolutely nothing. Pull up an Adirondack chair just outside of your room, pour a glass of local wine you purchased from the restaurant, watch the sun sink into the Pacific, and let the evening unfold without a plan. Even if you’re tempted, you’re in an isolated, remote part of the coast with very little to do and almost zero cell service. You may have just found the digital detox you didn't know you needed.
Day Two: Get Back Into Your Body
The next morning, head south to Cambria for a treatment at woman-owned Vyana Wellness Collective. Two of us had the self-proclaimed “best massages of our lives” there. Then lunch across the street at Robin's Restaurant, located in a restored adobe home with lush gardens. Robin's menu draws on farmers' market ingredients and global flavors, making it a much more interesting stop than a typical road-trip lunch.
After lunch is the highlight: meet the Clydesdales.
At Covell Ranch, Tara Covell and her family raise Clydesdale horses and offer both tours and trail rides. There's something so natural about spending an afternoon riding one of these enormous horses through the Central Coast. And that's exactly the point. When was the last time you did something simply because it sounded fun?
That afternoon, check into White Water Cambria, a stylish boutique hotel directly across from Moonstone Beach. The property blends modern design with the relaxed spirit of the Central Coast, and its amenities encourage you to get outside: complimentary bikes, a beach bag with supplies, local wines and snacks, and a charming basket of local goodies (including fresh pastries) delivered to your room every morning.
For dinner, head to woman-owned Brydge Restaurant, housed in a historic Cambria home and garden. The restaurant's micro-seasonal menu and local produce focus on the Central Coast's agricultural bounty, and chef Elaine brings a background that includes Chez Panisse lineage, Spain, and California's wine country. With a wine list that showcases the best of the Central Coast, this is the kind of meal worth lingering over.
Day Three: Get Curious
Start the morning with one of the trip's most interesting experiences: a seaweed foraging tour with Marley Family Seaweeds. Explore the coastline, learn about the seaweed growing there, forage alongside your guide, and turn your finds into a meal of a warm bowl of ramen. This analog experience with nature first thing in the morning is grounding and cleansing, with the ocean underneath your feet.
Then stop in Cayucos for lunch at Hidden Kitchen. The beachside restaurant serves its signature hand-pressed blue corn tacos and blue corn waffles, along with massive Instagrammable smoothies
From here, take a detour through the Edna Valley or SLO Coast wine country. You don't need to turn this into a full tasting marathon. Pick one winery, taste a few wines, and remember that wine country is as much about slowing down as it is about what's in your glass. You cannot go wrong with local producers, Laetitia Vineyard & Winery and Chamisal Vineyards.
Then head to Shuck Shack, a laid-back oyster and natural wine bar for dinner and, ideally, sunset, as it’s right on the beach. A dozen oysters with a glass of Pét-nat are not to be missed. As most spots on the coast, this is a place to linger. Time appears to stand still while slurping oysters and listening to the waves crash and the sun set.
End the evening at Sycamore Mineral Springs Resort & Spa in Avila Beach. Every overnight accommodation includes access to a private mineral spring tub, but the real treat is the property's hillside hot tubs: private open-air tubs tucked beneath mature sycamore and oak trees. A peaceful hot tub soak surrounded by nature is a gem of an experience.
Day Four: Ease Back Into Reality
Before heading home, make one last stop at Avila Valley Barn. Pick up something sweet, including baked goods with the local olallieberry; browse the farm stand for local produce; feed the animals; or simply wander. Depending on the season, you may find hayrides, pony rides, animal encounters, and U-pick fields. Holding a fresh roasted corn on the cob with the husks, topped with parmesan, mayonnaise, and Tajín, is a quintessential California experience.
The beauty of this road trip is that none of these experiences require you to be productive. You don't have to network with anyone on a Clydesdale or take a business lesson from a seaweed foraging tour. You just have to be there. For founders, that's harder than it sounds.
We spend so much time optimizing our schedules that we forget the value of experiences you can't optimize. A beautiful coastline. A really good meal. A mineral spring under a grove of trees.
The Central Coast offers all of that and reminds you that life is happening outside your inbox.
