Santa Monica to San Luis Obispo

This idyllic oceanfront city, bounded by a 3.5-mile-long beach, feels more like a weekend getaway spot than a city just a few minutes west of downtown Los Angeles. Hang out on the city’s broad beach or lively Santa Monica Pier (complete with its own amusement park). Or rent cruiser bikes to follow the Marvin Braude Coastal Bike Trail, aka “The Strand.” The paved, multi-use path follows the oceanfront for roughly 22 miles, from Santa Monica south to Torrance. It’s here along the pier that you can see the End of the Trail sign that now symbolically marks the end of Route 66. (The original end location was in Downtown Los Angeles, at 7th and Broadway.)

Santa Monica is also a place for serious shopping. Pedestrian-only Third Street Promenade is lined with big-name brands, galleries, movie theaters, and comedy shows, including open-air Santa Monica Place. Or visit one of Santa Monica’s outstanding farmers’ markets, which pop up weekly on city streets.

You can trace most of Route 66’s historic path heading east using a couple of great apps: the Route 66 Ultimate Guide or Route 66 Navigation.

In this city 40 minutes south of Santa Barbara, you’ll find miles of unspoiled beaches plus farm stands overflowing with picked-that-morning produce. Start your visit with a stop at Heritage Square, which hosts a summer concert series and where 15 Victorian homes open for weekend tours. Next, check out Oxnard’s two outstanding automotive museums. The Mullin Automotive Museum features exquisitely designed French cars from the Art Deco era while the Murphy Auto Museum will let you peruse 90 vintage American classics, including a 1903 Oldsmobile. For Oxnard’s wilder side, board an Island Packers catamaran to visit craggy Anacapa Island, a hiking wonderland that is part of Channel Islands National Park. From late December into April, set sail on naturalist-led cruises to see migrating Pacific gray whales.

Kicked-back relaxation finds a perfect home in this appealing coastal town roughly 65 miles north of Los Angeles. While antique hounds have long known to pull off the PCH to poke around Ventura, a new generation has started to discover the town’s microbreweries, smart eateries, cool clothes boutiques, and live music scene. The good news is that the revival of downtown Ventura has buffed things up while preserving the town’s sun-and-surf charm, where family-run cafes with two-table balconies serve espresso and an ocean breeze. (After all, the Pacific is only a couple of blocks away, and it seems as if locals are required to have surfboard racks atop their cars.) Down by the water, stroll the historic Ventura Pier. You can also catch the Island Packers boat to Channel Islands National Park.

Perfect architecture, and perfect setting. Santa Barbara, aka “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. Then explore the city’s forward-looking neighborhood—the rehabbed warehouses of The Funk Zone, now home to urban wine-tasting rooms, artists' studios, and cool boutiques.

Thanks to its rich history, small-town charm, and beautifully buzzing wine scene, Lompoc offers a unique Central Coast ambiance. Start in Old Town Lompoc, home to antique shops, the Cypress Gallery of fine art, restaurants, and dozens of public murals depicting Lompoc’s colorful past and present. History buffs will enjoy the Old Town Heritage Walk, a one-mile self-guided tour covering 18 stops including the Lompoc Museum. Visit the most extensively restored mission in California, La Purisima Mission, founded in 1787. (Wear comfortable shoes—the nearly 2,000-acre property includes 25 miles of hiking trails.) You’ll want to take a couple days to discover the nearly 40 wineries along the Lompoc Wine Trail. Start in the “Wine Ghetto,” a cluster of small wineries in an industrial park setting, then explore the elegant estate vineyards in the Santa Rita Hills.

There’s an unforgettable moment as you reach Pismo Beach. The coastal hills open up to reveal shimmering turquoise waters and long stretches of the San Luis Obispo County coastline, with glimpses of this vintage beach town hugging the shore. Take a walk out over the waves to watch surfers from the historic 1,200-foot-long Pismo Beach Pier, built in 1928. Saddle up for horseback through the dunes just south of town and all the way to the surf on guided outings with Pacific Dunes Riding Ranch. Tours with Central Coast Kayaks take paddlers into dramatic sea caves tucked into the craggy coastline north of downtown.

An iconic beach town deserves some traditional beach food and in Pismo you’ll find all sorts of timeless favorites. Spoon up some of the silky, award-winning chowder at Splash Café. Or bite into the black Angus burgers at Wooly’s Beach Bar & Grill, where the deck overlooks the sand. Pair gorgeous ocean views with fresh seafood at Oyster Loft (above Wooly’s) or Latin-inspired entrees at the Ventana Grill, two of the best sunset spots in town.

This friendly San Luis Obispo County beach town includes just a half-mile of beach and a small downtown, but don’t let its stature fool you—there’s lots to do. When you’re not enjoying the shoreline, stroll the promenade on Front Street and peruse its shops, bistros, and wine tasting rooms, including the cycling-inspired Peloton Cellars. For a quick lunch (and a good look at sea lions and sea otters), head to the landmark Harford Pier for delectable crab cakes at Mersea’s Seafood. Take a dip in the mineral waters of Avila Hot Springs, or dial up the activity level by biking or walking the Bob Jones Trail, which follows San Luis Obispo Creek. Then, enjoy a luxurious stay at Avila Village Inn, which is central to everything. Traveling with kids? Don’t miss the interactive exhibits at the Central Coast Aquarium.

With its nuanced food and wine scene, rich history and mellow vibe, San Luis Obispo (or as locals call it, SLO) is a Central Coast must-see. This college town has ranked in past surveys as one of the happiest cities in America.

Explore Mission Plaza and Mission San Luis Obispo de Tolosa. Enjoy live music on the plaza on summer Friday nights. Year-round the first Friday of the month offers Art After Dark, with downtown SLO galleries opening their doors for wine tastings, snacks, and chats with local artists. A few blocks away, every Thursday evening, you can find the city’s farmers' market, a showcase for SLO’s culinary landscape, including local tri-tip, tamales, and craft beer.

Be sure to pay a visit to the 110-room Madonna Inn when you are in town. You can finish the day with a slice of the famed pink champagne cake and then retire in one of its quirky themed rooms, such as the Caveman, the Love Birds, and the Fox and Hound.

SLO delivers the goods on the wine-tasting front. Bottles bearing the world-renowned Paso Robles appellation can be found only about 30 miles away. But don’t miss the nearby Edna Valley region, in particular the Chardonnays of Edna Valley Vineyard and the Pinot Noirs of Tolosa. Then, check out the under-the-radar wineries of Arroyo Grande Valley, including the sparkling wines at Laetitia Vineyard & Winery.