Road Trip from San Francisco to San Diego

September 24, 2018

Highway 1 along the West Coast of North America has long captivated travelers, from the Spanish missionaries of 400 years ago to today’s road-trippers. Follow along as we journey between San Francisco and San Diego, with stops at Inspirato destinations that elevate the road trip to luxurious getaway.

Sonoma County

Stay at the Wheelman House in Healdsburg. A suite at the Wheelman puts you a block away from downtown’s cluster of dining, wineries, galleries, and shopping. The hotel’s distinctive arched bedrooms lined with wood are meant to evoke the inside of a wine barrel.


Take the time to enjoy the wine at any number of wineries nearby, or just stroll over to a tasting room in Healdsburg. Williamson Wines (home to gold-medal Chardonnays) is just one of the more than 15 wineries with tasting rooms located within walking distance of each other. Explore the wine country with a stop at the historic Scribe Winery, led by fourth generation farmers and brothers, Andrew and Adam Mariani. No visit to Sonoma can go without a trip up to Repris wines’ exclusive Moon Mountain vineyard. 

Epicures or wannabe epicures must make a pilgrimage to Healdsburg SHED, a modern-day grange and farm where the valley’s foods and wines are celebrated through cooking classes, markets, and a café and bar. For a taste of the best of Sonoma, reserve a table at Barndiva, an unpretentious dining spot where hyper-fresh, local ingredients are the star attraction. The menu may look simple, but the tastes are decidedly not.

San Francisco

Stay at the Fairmont San Francisco. Your suite at the legendary Fairmont plants you in the middle of it all, blocks away from San Francisco’s high-end shopping and dining and concert halls and a short ride (via historic cable car, if you’d like) to the waterfront. Bonus: You can channel San Francisco history at the hotel’s famous tiki bar.

Head to the farmers market at the Ferry Building Marketplace for a look at the produce and provisions that will turn into dinners at some of the city’s best restaurants. Not there on market day? No problem, the building houses a variety of savory specialty shops. For a hands-on, deep-dive into the science of creativity, explore the Exploratorium, a one-of-a-kind science and art museum at Pier 15 on the waterfront that’s beloved by generations of locals.

Fine art lovers should hit the de Young, a museum renowned for its collection of American art and photography. Bonus: A visit takes you to Golden Gate Park where you can stroll through rose gardens and enjoy the city at play.

Carmel Valley

Stay at the Bernardus Lodge & Spa. Tucked in the magical Carmel Valley where the days are fog-free and warm, but the nights are cool, a cottage at the Bernardus features a working fireplace, patio, and a complimentary wine bar in the room.

Explore the highlights of the California Coast all in one place at Point Lobos State Natural Reserve where a network of trails leads to tidepools teeming with marine life and dramatic oceanside cliffs surrounding hidden beaches. With hundreds of art galleries located in Carmel-by-the-Sea there’s sure to be one that appeals to every aesthetic. The village rolls down to the beach, considered one of the best in the country thanks to its soft white sand that, incidentally, is ideal sand castle material. Besides art and the sea, the Monterey Peninsula is famous for golf. Including the links at Pebble Beach and the greens at Quail Lodge, golfers can tee off on 20 championship courses in the area.

Santa Barbara

Stay at the Belmond El Encanto. Perched above the Mediterranean-flavored city of Santa Barbara, the Belmond and its spa invite you to unwind after traveling down Hwy. 1 from Carmel. After freshening up, you can leave the car parked and take one of the hotel’s electric bikes downtown for dinner or a cruise along the beachside path.

The city’s Funk Zone puts some of the state’s best contemporary artists, breweries, and wineries all in one spot, conveniently located between the beach and the highway. Start the city’s Urban Wine Trail in the Funk Zone and follow it up to the whitewashed, tile-roofed historic Presidio neighborhood, home to the second- oldest building in California. All told, there are more than 20 wineries on the tour.

On your way south out of town, hop a boat out of Ventura to the wilds of Channel Islands National Park. Along the way, you may see dolphins, and even whales. Once on the islands, an abundance of seals, birds, and untrampled flora reveal a land untouched by humans.

Dana Point

Stay at the Monarch Beach Resort. This sprawling golf and beach resort climbs from the ocean into the coastal hills. Here, being active is the name of the game with a challenging golf course, tennis club, and multiple pools available to guests. And, of course, there’s the beach club.

Monarch Beach Resort
Try surfing or paddle boarding on the swells that break just off shore of the Monarch Beach Resort with help from one of the resort’s Surf Hosts, who will provide you with a board and private instruction. Want to go deeper? Schedule a SCUBA excursion to the underwater park just off Crystal Cove State Park, where you can swim through towering forests of kelp, keeping your eyes peeled for sea life, including lobsters.
You can also get your marine fix at the Pacific Marine Mammal Center up the road in Laguna Beach. There you can check out the center’s rehab work on sea lions, seals, and other rescued marine life.

Los Angeles

Stay at the London West Hollywood. Immerse yourself in Hollywood glitz and glamour at the boutique London West Hollywood, home to the city’s largest rooftop pool deck overlooking the sights. But best of all is the London’s location, minutes from the heart of Beverly Hills and Hollywood.

Go shopping. You can choose from the chic glamour of Rodeo Drive in Beverly Hills, the hip and influential boutiques along Melrose Avenue, or the beach-inspired collections found along Abbot Kinney Blvd. in Venice. See a show at the Hollywood Bowl, an historic outdoor concert venue that’s hosted the world’s greatest entertainers, from The Beatles to the Los Angeles Philharmonic. To hear the next big thing, head one block north to the Sunset Strip, home to multiple music clubs. 

Or for something completely different, check out a live show or movie at the Hollywood Forever Cemetery, a green oasis in the middle of Hollywood (and a real cemetery). The Los Angeles County Museum of Art is renowned for its collection of art. A must-see after dark is the Urban Light, an installation of 202 street lamps located at the entrance to the museum.

San Diego

Stay at The Lodge at Torrey Pines. Thanks to its PGA ProTour golf course and access to the beach, The Lodge, with its Craftsman-inspired architecture and décor, is California at its best. Tee off on the famed golf course or enjoy the day in the surf (the water’s warmer here), or explore the boutiques and eateries that populate the quaint beach towns north of the lodge along Hwy 1.

Reserve a seaside table at George’s at the Cove, a La Jolla institution renowned for its California cuisine. If the weather’s fair, you can dine atop its open-air terrace. From your perch atop George’s, you look down on the La Jolla Ecological Reserve and the La Jolla Sea Caves, natural wonders that can be explored by water, kayak, or from the beach. Take off from Torrey Pines Gliderport in a tandem paraglider and soar over the La Jolla coast, riding the stiff onshore breeze up and down the shore.

Other Adventures From San Francisco


Stay at the Fairmont Pacific Rim, pictured below. On the waterfront, near Stanley Park, the Fairmont’s location in the heart of downtown means easy access to the city’s best dining and attractions and a peaceful escape from the bustle.

Fairmont Pacific Rim

Take a day trip to Whistler and ride the PEAK 2 PEAK gondola strung between the tops of Whistler and Blackcomb mountains. At its highest, the 2.75-mile ride puts travelers 1,427 feet off the valley floor. Inside Stanley Park, you’ll find the Vancouver Aquarium, Canada’s largest and home to 50,000 sea creatures. Sample the region’s bounty at ORU, located in the Fairmont Pacific Rim, where executive chef Nathan Brown prepares a seasonally appropriate prix fixe menu for both lunch and dinner.


Stay at the Thompson Seattle. With Puget Sound views from most rooms and Nest, one of the hippest after-work rooftop bars in the city, the Thompson brings the best of Seattle to you.

Walk down the block to Pike Place Market. Yes it’s crowded and the birthplace of Starbucks, but during the summer harvest, some of the best produce you’ll ever taste is on sale. Pop music and culture fans must make a pilgrimage to the otherworldly building that houses the MoPOP (formerly the EMP Museum), where they can immerse themselves in all things music, science fiction, cartoons, and other pop-culture movements.

Most great cities have a central park where the city recreates and gathers. In water-centric Seattle, that destination is Lake Union, where kayakers, rowers, windsurfers, sailors, boaters, paddle boarders, and even seaplanes turn the water into a city park.


Stay at the Riverplace Hotel. You’ll understand why Portland is known as a city of bridges from your room at the Riverplace, located on the Willamette River right downtown. The Portland’s attractions are all a short bike ride away using the hotel’s free bikes and the city’s famous bike lanes.

Take a bike ride along the waterfront to the city’s trendy Pearl District, home to quaint boutiques and cafés, including the city’s beloved Stumptown coffee. Craft cocktails are a religion in Portland, and you can taste why at the Teardrop Cocktail Lounge.

A mere 60 miles east, Mt. Hood towers over Portland. It also makes for a lovely drive, climbing from the river valley to Timberline Lodge, where you’re rewarded with a view that stretches for hundreds of miles in every direction, and if you want, the option to ski a glacier in the middle of summer.