The first stop, between Los Angeles and Santa Barbara, may not feel all that far from the big city, but in mood, it’s a world apart. The Spanish Colonial, quasi-Mediterranean vibe is so strong that it’s earned the nickname “The American Riviera.” Most of the buildings are decidedly New World, though, built in the wake of a 1925 earthquake; in a classic silver-lining twist, locals took it upon themselves to reinvent the city with now-ubiquitous red-tile roofing and Spanish-style architecture.
Hand in glove with that aesthetic comes Ojai Valley Inn & Spa, a secluded resort on several hundred acres of wooded mountain valley. The whole enterprise is perfect for a long-weekend constitutional, all vintage adobe and sprawling, pristine grounds, not to mention the spa treatments or the championship golf course — and the greater Santa Barbara region includes mile after mile of Santa Ynez wine country.
A little farther north and things are getting good and slow; crowds thinning, windows permanently down, shoes beginning to feel like an empty social convention. Welcome to San Luis Obispo, the spectacularly beachy forefather of everything vintage and farm-to-table. Smack in the middle of the (highly walkable) historic downtown region sits Granada Hotel & Bistro, a revitalized gem of the vaudeville era given new life as a luxury boutique.
This brick-and-industrial-chic hotel makes for seriously scrumptious eats, leveraging the area’s fertile valleys for unrivaled produce and, yes, plenty of top-notch wine. Hell, the whole region comes off as one giant tasting room. Once you’re sated, make a beeline to Hearst Castle for the requisite tourist extravaganza, and then clear your mind of all that ultra-decadence with a kayak trip for two in Morro Bay — watch for elephant seals! — before the next stop.
Spiritual home of the Beats, this sainted swath of Bohemia demands a reverent approach. It’s not exactly hard to muster the emotion, mind: just try to look nonplussed on the vertiginous brink of the continent, drinking in an absolute doozy of a sunset from your perch atop these untameable cliffs.
It all comes to its zenith at Post Ranch Inn, Mickey Muennig’s inimitable Modernist foray into hotelry. Here, Big Sur’s outsize mojo infuses the redwood Tree Houses (not an exaggeration) and Ocean Rooms (edging the cliffs, roofed with wildflowers) alike, as well as the infinity pool, 1,000 feet above the Pacific. Make time for a meal at Nepenthe, purveyors of intoxicating views and the famous, ground-steak Ambrosia burger, and pop in at Esalen, whose hot springs promise (and often deliver) a spiritual renewal.
Further north we come upon the Monterey Peninsula, and by extension, the storied Carmel region, comprising historic arts colony Carmel-by-the-Sea as well as Carmel Valley’s gorgeous pine-and-oak terrain. Something of an artistic enclave, these regions have a long and fruitful relationship with the poets, writers, artists, and actors that have found a home here over the decades.
Expansive residences on the peninsula give way to cypress-lined, fog-shrouded beachfronts, then Steinbeck’s expanse of rich farmland and even volcanic formations in which endangered California condors roost. Breathtaking in every direction, really, including the environs of Bernardus Lodge & Spa, affiliate of Bernardus winery and vineyard — and not a bad place for a bit of gourmet extravagance, either.
For all its eccentric elements, this town still has plenty of down-to-earth charm to go around, and classic California style to spare. This is, after all, where the surf craze found its legs (board?) — much of that just-shy-of-nostalgia energy is alive and well at the Beach Boardwalk, an archetypical esplanade complete with carousel, coasters, corndogs, and cotton candy. It’s also about digging into the crunchy local aspect: nook-and-cranny artisanal shops abound, if you’re the shopping type or even just feel like a splash of retro-chic.
Speaking of which, steer yourself towards Joie de Vivre’s Dream Inn when you get a chance. It serves well as your Santa Cruz HQ, expertly balancing mid-century modernism with laid-back California cool. Perhaps foremost in the hotel’s appeal is the private pool, which neatly solves the problems of public-beach overcrowding and chilly waters in one fell swoop. Gather your strength for one last push to…