Highway One Classic
Thomas J. Story/ Sunset Publishing

Trip 5-7 days 10 stops

Highway One Classic

Follow one of the world’s most celebrated routes on this coast-hugging drive. You can start this trip at either end. Here, the trip begins in San Diego, at the southern end of the state, then travels north to beach towns, the bustle and excitement of Los Angeles, through elegant Santa Barbara and surrounding wine country, then north to more beaches and attractions in Carmel, Monterey, and Santa Cruz. End in the ultimate “City by the Bay,” San Francisco. 

San Diego
John Bahu

San Diego

1
San Diego
California dreamers, endless coastline & sunshine

Start in one of California’s sunniest destinations, not just in terms of the weather, but also in attitude. In the heart of the city, shop in Horton Plaza, or catch a baseball game at Petco Park. See the giant pandas at the San Diego Zoo. Next, explore one of the city’s diverse neighborhoods, Little Italy, North Park, South Park, East Village—pedestrian-friendly enclaves are the epicenter of San Diego’s burgeoning culinary movement, progressive art scene, and craft beer boom. Start your own sampling in North Park, the neighborhood bordering Balboa Park’s northeast side. Along 30th Street and University Avenue, enjoy farm-to-table cuisine and boutique wines at Urban Solace, or wing it at local favorite Carnitas’ Snack Shop (the menu changes daily depending on fresh produce and other ingredients available that day). Work off lunch by heading down to San Diego’s sparkling Mission Bay to rent stand-up paddleboards or kayaks. Finish with dining and dancing after dark in the lively Gaslamp Quarter. Splurge on a night at one of California’s iconic lodgings, the Hotel del Coronado, on idyllic Coronado Island, connected to the city by an arcing bridge that makes you feel like you’re a million miles away.

Continue your drive heading north on Highway One, with a visit to beautiful La Jolla (classy shopping and sidewalk cafés abound), ending in the California surf capital of Huntington Beach.

Next Stop
Huntington Beach (93mi/150km; 1hr32min)
Huntington Beach
Kodiak Greenwood

Huntington Beach

2
Huntington Beach
Endless summer, surfers paradise

Plan at least a day to hang out and get the surf vibe in this classic beach town, where the main drag heads straight to the beach. Southern California’s beach culture thrives along this city’s curving shoreline, where you can bicycle down an oceanfront path, play volleyball, and, of course, surf. Surfing definitely sets the tone in Huntington Beach, and even if you never grab a board, there’s shopping at leading surf retailers and great viewing of some of the local dudes riding the waves alongside the landmark Huntington Pier.

From the pier, it’s a short walk to Main Street’s stylish boutiques and restaurants, many with sidewalk tables or decks that let you bask in Huntington Beach’s fresh ocean breezes and sun-soaked afternoons. You can get a taste of the Surf City life with stays at Huntington Beach luxurious oceanfront resorts. Or discover more natural sides of town by trying horseback riding in 354-acre/143-hectare Huntington Central Park, and with bird watching and by exploring trails in Bolsa Chica Ecological Reserve, a restored wetlands and one of Southern California’s most vital coastal habitats.

Next, follow the coast north to California’s largest metropolitan area, Los Angeles, with big city museums, dining, entertainment, and other attractions.

Next Stop
Los Angeles (37mi/60km; 33min)
Los Angeles
David Jones/ Flickr

Los Angeles

3
Los Angeles
Rooftop Restaurants, A-List Celebrities

California’s largest city has nonstop action and things to do, but it can be a challenge to navigate, so planning your trip in advance is a big plus. Start in the coastal city of Santa Monica, with a wide, uncrowded beach, a signature pier topped by carnival rides and restaurants, and outstanding shopping at Third Street Promenade and fancy Santa Monica Place shopping center (great for rooftop dining with ocean and city views). Follow the Santa Monica Boulevard northeast to visit legendary Beverly Hills, where cars with tinted windows pull up to Chanel and other deluxe boutiques along Rodeo Drive. Continue east to Hollywood to stroll the Hollywood Walk of Fame and visit TCL Chinese Theatre.

Drive east to visit hip and historic downtown Los Angeles (or simply DTLA). An influx of new residents has helped energize the area, and downtown’s re-emergence has also been spurred by such attractions as Grand Park, an urban oasis with views stretching from the Music Center (including Walt Disney Concert Hall) to City Hall. Vintage buildings have been transformed, including the ornate 1927 United Artists building on Broadway, where the Ace Hotel Downtown Los Angeles offers stylish digs and a restaurant. Crowds flock to the sports and entertainment combo of Staples Center and LA LIVE, where you can also see music artifacts (Elvis’s sheet music, Michael’s glove) at the Grammy Museum and catch concerts at the Nokia Theatre. Finish your L.A. experience with a visit to Universal Studios Hollywood, with movie-themed rides and back-lot tours.

Return to the coast to drive north past Malibu and on to one of California’s prettiest cities, romantic Santa Barbara.

Next Stop
Santa Barbara (95mi/153km; 1hr38min)
Los Angeles’s Perfectly Prepared Eggs
California Dream Eater becomes an eggspert after visiting Eggslut downtown.
Santa Barbara
Santa Barbara Mission

Santa Barbara

4
Santa Barbara
With its Mediterranean climate and cache of culture, this seaside city deserves to be called the “American Riviera”

Next stop on your coastal cruise is this elegant city hugging the coastal hills, where classic Spanish architecture gives the region a sun-washed European look straight out of the Riviera. The Santa Barbara may have a burnished antique look, the current fantasy of Spanish colonial-style architecture—all red-tiled roofs and whitewashed courtyards covered in climbing bougainvillea—didn’t take root until 1925, when an earthquake damaged downtown buildings, making room for a whole new style. And in this case it was a romantic look back, a nod to the region’s first Spanish visitors more than 150 years before. The elegant building style has stuck around, and become the city’s visual touchstone.

Perfect architecture, and perfect setting. Tucked into the lee of the Santa Ynez Mountains and protected from the brunt of Pacific wind and waves, “The American Riviera” enjoys a dreamy Mediterranean climate, with plenty of sunny days and mild winters. Add wine country producing award-winning vintages, outdoor adventures on land and sea, big-city arts and entertainment, and you have a city that’s a poster child for the California good life. Stroll State Street for excellent shops and dining, launch a kayak from East Beach to paddle under Stearns Wharf, visit the classic Old Mission Santa Barbara, and tour the 1782 presidio for a look at original adobes like El Cuartel, the second oldest surviving building in the state.

Now drive north to sample the region’s legendary vintages in beautiful, uncrowded wine country.

Next Stop
Santa Ynez Valley (31mi/50km; 39min)
California Dream Eater visits Empty Bowl gourmet Noodle Bar in Santa Barbara
Santa Ynez Wine Country
Laura Flippen

Santa Ynez Wine Country

5
Santa Ynez Wine Country
Tour an iconic wine region with fog, sun, and plenty of Pinot

This next stop encourages you to slow down, relax, and really savor your surroundings—and the amazing wines produced here. The Santa Ynez Valley, just north of Santa Barbara, is one of most diverse grape-growing regions in the county. Near the Pacific, fog and cool air rolls in at dusk, ideal for Chardonnay and Pinot Noir grapes. Thirty miles inland at Happy Canyon, it’s sunny and hot—perfect for Bordeaux varieties like Cab Franc and Merlot.

And scenic? How about rolling hills, endless vines, and ancient oaks to the horizon. Between the wines and the views, it’s easy to see why the region became a star in the 2004 surprise hit, Sideways. Take a self-guided tour of the film’s many shoot locations in Buellton, Los Alamos, and Los Olivos—even if you don’t remember the movie, these places are all worth a visit.

Where to go? Why not start at Sunstone Winery. It has a cool wine cave, sustainably grown grapes, and a spectacular limestone chateau available for overnight stays. Another tip: buy a pass from Santa Ynez Valley Wine Country Association to save on tastings at 15 participating boutique wineries.

Next stop is a visit to one of the state’s—if not the country’s—remarkable structures, the ornate compound known as Hearst Castle.

Next Stop
Hearst Castle (109mi/175km; 1hr53min)
Hearst Castle
Kodiak Greenwood

Hearst Castle

6
Hearst Castle
Wraparound Views, Lavish Designs

From Highway One, you’ll see this incredible complex of ornately embellished towers and buildings perched high on a coastal hilltop, like a coastal Shangri-La with 360 views. Park in the main lot of the state park grounds, then check in at the visitor center to ride one of the park’s shuttle buses up to the castle for a guided tour. (Make online reservations well in advance, especially during the busy summer months.) Lavishly designed by Julia Morgan (California’s first female licensed architect), as the private residence of publishing magnate William Randolph Hearst, the complex, completed in 1947, is an extraordinary temple to opulence and excess. Now showcased within one of California’s most visited state parks, it is a must-see to end all must sees, an eye-popping extravaganza with a 165-room castle, 127 acres/51 hectares of terraced gardens, fountains, and pools.

In fact, the castle’s two pools are standout attractions. The outdoor Neptune Pool, 104 feet/32 meters in length and with an oil-burning heating system, evokes ancient Greece and Rome, with marble statues of Neptune and Nereid guarding over the aquatic paradise. The second, smaller indoor Roman Pool has the look of a decadent Roman bath, with rich details including cobalt blue and gold smalti, or glass tiles. Look up to see intricate mosaics depicting a star-filled night sky, spreading across the roof and dome. The pool is surrounded by eight marble sculptures of Greek and Roman gods, goddesses, and heroes, carved by Italian sculptor Carlo Freter.

From Hearst Castle, turn north to twist along the iconic Big Sur—with towering redwoods, and sheer cliffs plunging into the sea.

Next Stop
Big Sur (81mi/130km; 2hr16min)
Big Sur
Myles McGuinness

Big Sur

7
Big Sur
Art and nature merge on this rugged coast, one of California’s most spectacular settings

Welcome to one of the world’s most unforgettable stretches of coastline. This roughly 90-mile-long stretch of redwood- and fog-trimmed waterfront between Carmel-by-the-Sea and Hearst Castle has no specific boundaries, no urban core, drawing you (and writers like Henry Miller and Beat Generation darling Jack Kerouac) in with a magic allure that is almost palpable. This is, quite simply, a place you want to be—bluffs, sea, and sky.

"This is, quite simply, a place you want to be—bluffs, sea, and sky."

Drive Big Sur’s length via twisting Highway One, with plenty of pullovers at places like Bixby Bridge. Another favorite photo op: McWay Falls, a silvery cascade that falls some 70 feet from the sea cliffs to a remote beach below. Look up to see endangered California condors, North America’s largest birds, or look down to scan the swells for migrating whales or sea otters floating among dense beds of kelp, California’s signature seaweed. Try the famous Ambrosia burger on the deck of Nepenthe, then nurse your beer to watch the sunset. Campgrounds abound, as do rustic cabins at Deetjen’s and other (sometimes funky) resorts. The region’s beauty also makes it a magnet for exclusive, splurge-worthy hotels like the cliff-hugging Post Ranch Inn, or luxurious Ventana Inn and Spa.

Continue north along Highway One towards your next stop, romantic Carmel and historic Monterey. Along the way, consider a detour to explore Andrew Molera State Park, where you can ride horses right next to crashing waves.

More Ideas
Next Stop
Monterey/Carmel (23mi/37km; 57min)
Monterey & Carmel

Monterey & Carmel

8
Monterey & Carmel
Romance and a big blue sea

Wrapped by the Pacific on three sides, the Monterey Peninsula at once offers wind-tossed beaches and quiet coves, fine dining and casual eats, early history and postmodern art. You’ll first arrive in artsy Carmel-by-the-Sea (locals just call it Carmel), a town that deftly straddles the balance point of rich history and new wealth. The Carmel Mission is one of the state’s most beautiful, and shady trails fan out from the site into lush Mission Trail Nature Preserve. Stroll the white sands of dog-friendly Carmel Beach, or explore a mosaic of meadows, wave-battered bluffs, and wind-twisted trees at nearby Point Lobos State Reserve. Come back to explore Carmel’s main village, with gallery-lined streets, cozy gastropubs, and even cozier inns.

Continue around the arc of Monterey Bay to visit the world-renowned Monterey Bay Aquarium, with its psychedelic jellies and bat-ray petting tanks is a must-visit, especially for families. Mesmerizing tanks and exhibits showcase more than 35,000 animals and plants representing over 550 species—a large number of them California natives, including California sea otters. Insider tip: Get tickets online in advance to skip long lines.

Step outside and find yourself among hotels, shops, and restaurants filling former fish-packing plants along Cannery Row, made famous by local author John Steinbeck. Rent bikes to follow the coast south around the peninsula to Pacific Grove, Asilomar State Beach, and the sea-and-spray beauty (and gazillion-dollar homes and celebrated Pebble Beach golf courses) along the 17-Mile Drive.

Continue north to the boho-funky beachfront town of Santa Cruz, where surfers carve waves and kids play on a classic waterfront boardwalk.

Next Stop
Santa Cruz (44mi/71km; 49min)
California Dream Eater vists Mundaka in Carmel
Santa Cruz
Tai Power Seeff

Santa Cruz

9
Santa Cruz
Surf's up at NorCal's friendly beach getaway

This ultra-mellow beach town has a decided split personality—and both sides are cool. First, there’s the woo-hoo family fun of the Santa Cruz Beach Boardwalk, a yesteryear-style esplanade lined with classic coasters, arcade games, corn dogs, and a historic carousel. Then there’s downtown Santa Cruz, where local college students browse for vintage and boho chic, and relaxed restaurants focus on organic, local ingredients.

But at its heart, Santa Cruz is a surf town. This is where the sport was originally introduced in California, and top surfers know that the place to be is Steamer Lane. Need more proof? Nearby lives Jack O’Neill legendary surfer and force behind the O’Neill empire, pioneer of the wetsuit and elder statesman of everything surf in the Golden State. 

In the center of town, away from the beachfront crowds, Pacific Avenue offers many shops with a local twist, including the venerable O’Neill’s where surfer guys and girls can find a bikini or board shorts, flip-flops, or a wetsuit—the creation and design of the city’s favorite son, the legendary Jack O’Neill (he still lives a beach ball toss from the beach here). The independent Bookshop Santa Cruz is packed with happy locals, especially during frequent author talks, and many other boutiques offer art, clothing, and home furnishings (check out the gorgeous artisanal glass at Annieglass).

Next, travel to your last stop—the beautiful “City by the Bay,” San Francisco.

Next Stop
San Francisco (73mi/117km; 1hr20min)
San Francisco
Myles McGuinness

San Francisco

10
San Francisco
Sparkling Bay, Magic City

Finish your trip in one of the world’s great cities. For a novel way to visit “the City by the Bay” park your car and explore by foot, bike, and unique public transportation. Pedal bikes across the Golden Gate Bridge and back, then explore the lush Presidio, a former military base that’s now a park, or head into Golden Gate Park to visit museums and row across a secret gem, Stow Lake. Continue along the flat Embarcadero to Fisherman’s Wharf and the Exploratorium science and learning museum. Park your bikes and hop a cable car to ride over the hill to the high-end shops and enormous Macy’s, NikeTown, Saks Fifth Avenue, and Neiman Marcus around bustling Union Square, with a stop for Italian pastries and cappuccino at Emporio Rulli right in the square. Nearby, stroll boutique-lined Maiden Lane—pedestrian only thoroughfare during the day, when cafes set up tables and chairs right in the street. Nearby Westfield Mall, a dazzling complex on once scruffy but now spiffed up Market Street, glitters with even more stores, including an deluxe food court on the lower level. At night, catch a show in the theater district, or head to North Beach to see Beach Blanket Babylon, a raucous and irreverent San Francisco institution. For more nightlife and dining, stroll Valencia Street in the Mission, a trendy and eclectic hotbed of restaurants and bars, and awesome late-night scoops at Bi-Rite Ice Cream—sweet way to finish your road trip.