Skip to main content
  • Relaxing on the beach at Dana Point Headlands Conservation Area in California
    View more

    Dana Point: Laid-back Luxury Meets Surfer Culture

  • An off-road tour with Big Bear Jeep Experience in Big Bear Lake, California
    View more

    Big Bear Lake: Southern California Mountain Retreat

  • Sipping wine at the Deep Sea Tasting Room on Stearns Wharf in Santa Barbara, California
    View more

    Santa Barbara: Coastal, Cultural and Always Chic

  • Kayaking with a view of Morro Rock in San Luis Obispo County, California
    View more

    San Luis Obispo County: Farm-to-Plate Escapes & Cultural Icons

Watching the sunset from Elephant Seal Vista Point in San Simeon, California
View more

Southern California Road Trip: Coastal Escapes and a Mountain Retreat

By Zaida Rios

  • Route distance:
    970.00
  • Suggested Time:
    1-2 weeks

From laid-back coastal towns to a quaint mountain escape, this road trip makes the most of all the fun to be had in and around Southern California’s waters.

Unwind on a gorgeous coastal voyage with an adventurous detour into the mountains. Get excited because you’re about to see stunning waterfronts, get an architectural education, sip wine, spot marine life and embrace California’s allure. Fly into Los Angeles International Airport (LAX), rent a car and head to Dana Point via Interstate 405 South to begin an unforgettable journey.

01
Relaxing on the beach at Dana Point Headlands Conservation Area in California
View more

Dana Point: Laid-back Luxury Meets Surfer Culture

Dana Point is a true surfer haven, where chill vibes and luxury amenities blend easily. The best place to be in Dana Point is the beach. Low tide reveals ocean treasures in the area’s diverse tidal pools, while high tide brings the waves. Catch them on a surf lesson at Salt Creek Beach or Doheny Beach, both ideal spots to learn or observe Dana Point’s cool surfer culture. After conquering the swells, carve out time to laze about the beach under a cabana with a cocktail in hand at the Monarch Beach Resort. Nearby, you’ll catch sight of the stunning Ritz Carlton Laguna Niguel perched on a rocky cliff. Move above sea level to take in lovely vistas and local flora at the Headlands Conservation Area. Follow the wooden boardwalk as you ascend the peaceful nature trail. Once at the top, breathe in the sweeping landscape – a bird’s-eye view of Dana Point and the Pacific Ocean. Back in town, pop into Hobie, Killer Dana or Jack’s Surfboards for beachy accessories, clothing and surf gear; or explore Dana Point Harbor’s fun-loving scene and marina views. Before you head into the mountains, why not get into the boating culture with a sailing lesson, or spot some wildlife on a dolphin or whale watching cruise? You'll soon see why Dana Point calls itself the Dolphin and Whale Watching Capital of the World™.

170 km
2.5 hours by car
02
An off-road tour with Big Bear Jeep Experience in Big Bear Lake, California
View more

Big Bear Lake: Southern California Mountain Retreat

Say goodbye to the coast and hello to the San Bernardino Mountains, home to one of California’s most beloved outdoor escapes – Big Bear Lake. Popular for its exceptional alpine skiing, snowboarding and lake activities, this charming mountain outpost is small enough to feel cozy but big enough to offer versatile outdoor adventure. As a four-season getaway, warmer months usher in an array of mountain-based and lakeside activities too. Jump on the cool Scenic Sky Chair ride at Snow Summit’s Bike Park, which peaks at 2,500 meters, offering views of Big Bear Lake and the San Bernardino National Forest. Want to get off-the-beaten path? Hit the rugged mountain biking trails, or sign up for the Big Bear Jeep Experience and drive off-road jeeps on a guided tour. You’ll traverse mountain terrain and explore an old gold mine while also learning about local flora and fauna. Head to Big Bear Lake for fun on the water: Kayak, fish, jet ski or take a lazy sunset pontoon cruise. You’ll get a warm welcome at The Village at Big Bear Lake, a picturesque assortment of local eateries and cute shops. Shop for outdoor essentials, chic mountain clothing and decor, family-friendly toys, old-fashioned candy and more souvenirs. You’ll want to pick up a memento or two from your mountain retreat before you head back to the coast.

298 km
4 hours by car
03
Sipping wine at the Deep Sea Tasting Room on Stearns Wharf in Santa Barbara, California
View more

Santa Barbara: Coastal, Cultural and Always Chic

Head back west toward the Pacific Ocean to see another side of coastal life in Santa Barbara. This elegant, waterfront city taps into so many vacation favorites, from architecture and historic sites to artisanal food and local wine. To see that quintessential Santa Barbara look, start at the Santa Barbara County Courthouse. Located downtown, this stunning Spanish Colonial Revival building is a city icon, which you can explore with a free docent tour. Once inside, you can also climb to the top of the clock tower for a panoramic view of Santa Barbara and beyond. For a taste of local flavor, pop into the Santa Barbara Public Market, a trendy marketplace offering locally and regionally grown food, as well as wine and beer. Hang out for lunch or pick up supplies for a picnic on your way to the A.C. Postel Mission Rose Garden, another must-see stop for architecture buffs. Meander the grounds and spot neatly manicured rose garden collections framed by views of the 200-year-old Spanish Colonial mission. Want a unique way to keep exploring the city? Set off on the self-guided Urban Wine Trail to taste varietals from the best local vineyards on a fun wine hop throughout the city. Start your sipping tour in the festive Funk Zone, one of the city’s most vibrant entertainment districts. Don’t skip strolling out to Stearns Wharf to visit the Deep Sea Tasting Room from Conway Family Wines. It’s a special treat to sip wine while gazing at 360-degree views of the Pacific Ocean at sunset.

173 km
2 hours by car
04
Kayaking with a view of Morro Rock in San Luis Obispo County, California
View more

San Luis Obispo County: Farm-to-Plate Escapes & Cultural Icons

Cruise northwest along the ultra-scenic Pacific Coast Highway into San Luis Obispo County (nicknamed SLO CAL), which includes coastal getaway Pismo Beach and one of the country's largest wine regions, Paso Robles. Your first stop is Morro Bay, known for the volcanic formation Morro Rock jutting impressively out of the horizon. Go on a kayaking tour for up close views and to spot sea lions and harbor seals. After your excursion, plan on lunch at Tognazzi’s Dockside Restaurant, where even more epic views of the bay will accompany your seafood pasta. Next, take a scenic drive north to Moonstone Beach and the Moonstone Boardwalk in Cambria – wonderful places to explore and photograph. After a beach stroll, venture to San Simeon, home to Hearst Castle. A National Historic Landmark, this opulent architectural gem overlooking the Pacific Ocean is the former estate of newspaper tycoon William Randolph Hearst and a must-see in SLO CAL.

Another can’t-miss can be found inland in Edna Valley, one of two wine regions in the area, located between San Luis Obispo and Pismo Beach. Make your first stop at Baileyana, a boutique winery known for chardonnay, pinot noir and syrah varietals. Tastings are conducted in a historic schoolhouse built in 1909, which is a clever way to sip a crisp glass of chardonnay. Feeling outdoorsy? Sign up with an outfitter to explore the wine region via a bike tour. Pedal your way to various tasting rooms while enjoying the camaraderie of fellow riders and wine enthusiasts. After your adventure, choose from a variety of lodging options and spend a night or more in one of SLO CAL’s picturesque cities. Life here is too beautiful to rush, so take your time before driving just over three hours south to Los Angeles or north to San Francisco to fly home.