Pacific Coast Highway South

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.

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.

Five islands off the Southern California coast—Santa Cruz, Anacapa, Santa Rosa, Santa Barbara, and San Miguel—comprise Channel Islands National Park, one of America’s most remote—and utterly magical—national parks. Visitors arrive on the islands by boat (boats depart regularly from Ventura and Oxnard) or small plane, then use their hiking boots or kayaks to get around. Revered for its endemic plants and plentiful wildlife, the “Galapagos of North America” has no lodgings (there are campgrounds, however), stores, or restaurants—a place that draws you in without a lot of extra trappings. On this ocean sanctuary, it’s all about wraparound beauty, solitude, and the chance to totally and completely unplug.

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.

With beaches and marinas along its waterfront and a busy dining and shopping scene on downtown’s Pine Avenue, Long Beach blends big city sophistication with resort town fun. Tour the legendary, permanently docked ocean liner Queen Mary, then relax with a drink in the ship’s Observation Bar—you can even stay overnight in one of the ship’s cabins. Special exhibits are on display throughout the giant ship, and wandering through the various levels to see them feels like a journey through a time warp—you can almost imagine a bygone time of ladies in velvet and lace coming down the ship’s main staircase for dinner with the ship’s captain.

Also along the waterfront, outstanding Aquarium of the Pacific has huge tanks and displays featuring coral reefs, goofy Magellanic penguins, and other ocean habitats. For beach-town style, head to the Belmont Shore neighborhood. East Village, home of the Museum of Latin American Art, has an edgier, hipster vibe.

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 just 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 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, head southeast to Costa Mesa, hub of some of the state’s best shopping destinations.

The name of this upscale Newport Beach hamlet translates to “crown of the sea,” and it’s a fitting moniker—this is where the gilded life meets classic Southern California beach culture. Corona del Mar is loaded with coastal gems, from the popular Big Corona beach (the spot to paddle out for a surf session) to the strip of shops and eateries (head to Gulfstream for fresh oysters) lining Pacific Coast Highway. Check out nearby Fashion Island, a shopping, entertainment, and culinary destination, then head to Little Corona beach to explore the tidepools. Cap your day with the epic sunset views at Inspiration Point.

In 1912, an early Laguna Beach artist described finding a rugged coastline “with cove after cove and headland after headland, golden cliffs and deep blue and purple ocean and clear emerald pools, lazy sea and pounding surf.” More than 100 years later, that’s the world you can still experience at this 2,400-acre coastal parkland. Explore winding trails leading into the foothills on foot or mountain bike. Walk along the park’s 3 miles of coastline to find your own perfect sandy crescent with family-friendly waves.

Another find here: Crystal Cove State Park Historic District, where you can order an ahi tuna burger at The Beachcomber at Crystal Cove, or pick up a creamy shake from Crystal Cove Shake Shack (formerly Ruby's Shake Shack) to take back to your beach blanket. There is also a charming collection of vintage beachfront cottages, rustically restored and available for overnight stays. (Note: reserving one of the 21 extremely popular cabins takes patience and perseverance; check the website for details.)

Laguna Beach is a coastal paradise—from its bright hillside cottages to its downtown streets—coming together at the edge of a sparkling blue sea. This is a grownup play land, with romantic hideaways, rooftop restaurants perfect for toasting the sunset, and a coastline dotted with protected crescents of sand—some attracting the local surfer crowd, some family favorites, and some perfect for a peaceful escape.

The town—first settled as an artist’s colony—is filled with quality galleries. Painters often perch their easels along the bluffs—watch them create a pretty seascape before your eyes. Or dip into the hushed galleries of the Laguna Art Museum, with its excellent collection of contemporary works by California artists, such as Wayne Thiebaud and David Gilhooly. Laguna Beach is also home to summertime’s remarkable Pageant of the Masters, a one-of-a-kind event where classic artworks are recreated using brilliantly painted tableaux, all populated by real people done up to replicate figures in the original paintings. The festival is wildly popular and performances always sell out, so get tickets well in advance.

End your trip at this sunny, waterfront city. Downtown, shop the many independent boutiques throughout the historic Gaslamp Quarter, 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 tapas, craft beer, and mimosas (their specialty) at Palmy's, or wing it at local favorite Carnitas’ Snack Shack (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.