21 Ultimate Road Trip Itineraries from San Diego

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1–2 Hours | 3–4 Hours | 5–6 Hours | 8 Hours | National Treasures


1–2 Hours


Palm Springs

Why We Love It: The desert is a bright spot with cool options for a no-children getaway

We love kids, but sometimes we want to enjoy our mimosas and pool time in peace. Thankfully, Coachella Valley has new destinations for travelers without tots. Open since October, the adults-only Villa Royale is a Mission Revival–style property with 38 rooms and pet-friendly amenities (dog beds, bowls, treats).

Or try Sparrows Lodge, a 21-and-over boutique hotel with a hip country-cool vibe and elegant outdoor dinners every Wednesday and Saturday. In town, get to Rooster and the Pig when it opens at 5 p.m.—the no-reservations, dinner-only pan-Asian restaurant is a hot ticket in town for those in the know, and the wait is worth it for crispy beef noodles and black pepper tofu.

21 Ultimate Road Trip Itineraries from San Diego

If you want to get away from the hustle and bustle, there’s no prettier stay than Sands Hotel & Spa (for guests 18 and over) in Indian Wells, site of this month’s BNP Paribas Open tennis tournament. The Moroccan-inspired hotel is decked out in blush tones, ornate tile work, a three-room spa, and the Pink Cabana restaurant, a print-happy nod to retro tennis and racquet clubs. And even if you go to the scene-y Parker Palm Springs, don’t miss the somewhat secret Counter Reformation, a monastery-chic indoor wine bar tucked into their back garden.


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Valle de Guadalupe

Why We Love It: There’s a new crop of resorts and restaurants in Mexico’s wine country

Maybe you’ve been to Finca Altozano, Laja, and Deckman’s, and you’ve already stayed at La Villa del Valle and Encuentro. So let us introduce you to el Valle’s impressive freshman recruits. The Villas at El Cielo Winery Resort debuted in November with 95 suites and 33 villas, two restaurants, and a café adjacent to the five-year-old winery, all spanning 79 acres.

21 Ultimate Road Trip Itineraries from San Diego

In August, Hotel Partana opened its six-room steel-and-wood-heavy property on the same site as Finca (chef Javier Plascencia’s alfresco ode to wood-fire cooking), Lupe (his food truck serving tortas and ice cream), Animalón (his pop-up dinner series hosted beneath a 200-year-old oak tree), and Das Cortez (a trendy coffee kiosk).

This summer, look for glamping staple CuatroCuatros in nearby Ensenada to open new cabins, plus a spa and Japanese restaurant. And in the fall, the Valle Food & Wine Festival—which last year drew major chefs like Nancy Silverton and Dominique Crenn—is rumored to be returning for food, music, and oenophilic pleasures.


Pit Stop!

Just across the border in Tijuana, take in cocktails and food from the famed Tacos Kokopelli at the new Cereus Bar, located in the trendy live-work space Estacíon Federal.

Laguna Beach

Why We Love It: A new hotel is breathing fresh air into the quirky beach town

We’ve always appreciated the pristine beaches, electric sunsets, and funky art scene in Laguna Beach, but thanks to the somewhat uninspiring hotel scene, it’s usually a day trip rather than a multi-day excursion. That’s changed with Hotel Joaquin, a 22-room boutique property on the beach from the same team behind Korakia Pensione in Palm Springs. It’s understated sexy, best suited for adults and friend groups. Breakfast and gear like bodyboards and surfboards are free, and it’s a quick two-minute walk to the beach.

21 Ultimate Road Trip Itineraries from San Diego

Around town, Trap Door Dining hosts seasonal pop-up dinners for 15–20 guests led by chef Kenny Seliger, who previously worked in the kitchen at Montage Laguna Beach. His next dinner takes place March 23 at Newport Beach’s Kit Coffee with a four-course meal of whipped burrata, spring peas with pork belly, and a vanilla shortcake with blueberry jelly.

Los Angeles

Why We Love It: City of Angels? Try City of Creatives.

Don’t let proximity stop you from enjoying LA’s current renaissance. Finally there’s a chic place to rest your head on the east side: The upcoming Silver Lake Pool & Inn, due next month, has a vintage California feel—wood facades, open layouts, greenery, and natural light aplenty.

Farther west, Culver City is now a destination in its own right thanks to the vibrant, two-month-old Palihotel Culver City, with 49 rooms outfitted in modern decor and art deco touches. They say nobody walks in LA, but from the Palihotel it’s no more than 20 minutes to BäcoShop for Middle Eastern eats, Destroyer for Scandinavian-style plates, and Arcana for coffee table books on fashion and photography.

Elsewhere in the city, clock in at least one meal at Fiona, the new all-day eatery near Melrose serving Asian-inspired dishes as well as can’t-miss desserts—owners Shawn Pham and Nicole Rucker previously worked at the Southeast Asian spot Simbal and carb temple Gjelina, respectively.

21 Ultimate Road Trip Itineraries from San Diego

Looking for a more classic stay? The Hollywood Roosevelt, site of the first Academy Awards 90 years ago, is a posh boutique option with The Spare Room, a hybrid cocktail bar and bowling alley within the hotel.


Leave the car at home!

Board the Pacific Surfliner train from downtown, Solana Beach, or Oceanside and get to LA in under 2.5 hours. You can use The Freehand as a home base—the 13-story downtown hotel has apartment-style lofts, traditional rooms, and coed or female-only shared accommodations with bunk beds, less than two miles from Union Station. And don’t miss yoga on their colorful rooftop.


21 Ultimate Road Trip Itineraries from San Diego

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3–4 Hours



Why We Love It: Post-wildfires, the ’bu needs your support

Last fall’s deadly fires wreaked havoc on the tony coastal enclave, obliterating at least 670 structures. Now it’s time to pour some money back into the community. The Surfrider Malibu combines classic SoCal beach culture with high-end details. Beachfront rooms are decked in whites and blond woods, fitted with rain showers and outdoor terraces, and in the suites, hammocks.

21 Ultimate Road Trip Itineraries from San Diego

If you can pull yourself away from the property, the front desk can arrange "surf safaris" and hiking trips. It’s a similarly serene vibe at Nobu Ryokan. With only 16 rooms, the Japanese-style inn embraces its East Asian influences with teak soaking tubs, linen yukata robes, and tatami mats. Plus, it’s just a short walk to Nobu Malibu for their famous sushi, sashimi, and Japanese fusion dishes. To take in that fresh sea air, lace up for a hike to Mugu Peak, a five-mile trek past meadows and mountains that leads to a panoramic ocean view.


Why We Love It: The SoCal town specializes in next-level luxury

In the high-end beach community of Montecito, which counts Oprah among its residents, the weeks-old Rosewood Miramar Beach promises luxury and seclusion from the wineries, restaurants, and State Street hubbub in Santa Barbara just five miles away. The resort feels more like an estate, with 161 rooms over 16 acres, plus seven restaurants, a yacht-inspired beach bar, the farm-to-table eatery Malibu Farm, two pools, The Gatehouse (a concept store curated by James Perse), and a Goop boutique, selling Gwyneth Paltrow–approved skin care, clothing, and gifts.

21 Ultimate Road Trip Itineraries from San Diego

Want to really splash out? Book one of the eight seats in the restaurant-within-a-restaurant The Silver Bough at the Montecito Inn. For $550 per person (tax and gratuity included, phew!), each diner is treated to an 18-course meal with pairings—anything from bone-marrow-stuffed potato to dishes made with locally caught box crab—available Thursday through Sunday by reservation only (they’ll accommodate vegan and pescatarian menus upon request).

21 Ultimate Road Trip Itineraries from San Diego

For a little more energy and walkability, head west to Santa Barbara for gourmet versions of Thai and Vietnamese street food at the new Tyger Tyger in the Funk Zone, a neighborhood of warehouses turned wineries and restaurants.


Leave the car at home!

It’s about five hours via the Pacific Surfliner to Santa Barbara, with an ocean view most of the way. The station is conveniently located less than a mile from the Funk Zone, for wineries and restaurants and the Mediterranean-inspired Hotel California.

Joshua Tree

Why We Love It: Geek out beneath the night sky

Designated an International Dark Sky Park two years ago, Joshua Tree National Park is celebrating its fifth annual Night Sky Festival on September 21, pegged to the fall equinox. Tickets go on sale this summer for the event, which will have 20 telescopes, astronomy lectures, photo booths, music, nature walks, and crafts for kids. (The park website has some recommended night-sky etiquette, like using red flashlights instead of white.)

21 Ultimate Road Trip Itineraries from San Diego

When you’re not hiking, rock climbing, or observing the stars, check out the year-old boutique Shop on the Mesa, stocked with desert-chic decor, including many locally made pieces. And while options for food in town are limited to vegan eats at Natural Sisters Cafe and Pie for the People! pizza, make time for La Copine, a surprisingly polished restaurant in nearby Flamingo Heights started by a Philadelphia couple who honeymooned in Joshua Tree and fell in love with it, then took over an old diner. The menu has high-end fare like grilled flatbread with whipped ricotta and a lamb burger topped with harissa—a far cry from those campfire hot dogs.

21 Ultimate Road Trip Itineraries from San Diego


Why We Love It: One tiny town packs a ton of eclectic festivals

Beyond its hippie ethos, famous "pink moment" sunsets, and the luxurious Ojai Valley Inn & Resort, the tiny town of Ojai (population 7,400) is also a hub for nearly a dozen annual festivals. Things kick off over Memorial Day Weekend with Art in the Park, a two-day celebration where nearly 100 fine artists sell their work in a show hosted by California’s oldest art nonprofit. On June 6, the 73rd annual Ojai Music Festival returns with four days of classical music at the Libbey Bowl amphitheater. This year’s event pays tribute to composers with ties to Ojai, including Igor Stravinsky. June 9 brings the Wine Festival, when more than 60 wineries and 30 breweries pour into town.

21 Ultimate Road Trip Itineraries from San Diego

Want to enjoy Ojai Valley’s bounty? The Lavender Festival on June 29 has local farmers selling soaps, oils, and decor made from the versatile flower. And due in August and October, respectively, the Playwrights Conference gives audiences a seat to workshop performances from new writers, while the Storytelling Festival brings together storytellers from across the country to perform personal narratives, ghost stories, folktales, and more. When you need some mid-festival fuel, be sure to visit the recently reopened cafe Hip Vegan for wholesome salads, sandwiches, smoothies, and desserts.

21 Ultimate Road Trip Itineraries from San Diego

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5–6 Hours


Death Valley

Why We Love It: Views that are so out-of-this-world, they’ve stood in for Star Wars planets

It may be the "hottest, driest, lowest national park," but you’ll forget that when you’re splashing around the spring-fed pool at the revamped Oasis at Death Valley (formerly Furnace Creek Resort), the 92-year-old resort composed of Inn at Death Valley (66 rooms plus 22 casitas) and Ranch at Death Valley (geared toward families, with 224 rooms). The property just unveiled a $100 million makeover that includes refreshed rooms, a spa, and a new restaurant and cocktail lounge, all surrounded by date palms and sweeping mountain views.

21 Ultimate Road Trip Itineraries from San Diego

You can book sunset and moonlight horseback riding excursions with Furnace Creek Stables or tee off at The Furnace Creek Golf Course. Within Death Valley National Park, see shooting locations from A New Hope and Return of the Jedi at Golden Canyon and Dante’s View terrace, or visit Badwater Basin to see otherworldly salt flats located at the lowest point in North America.


Why We Love It: The college town has grown up

Dated strip malls, fraternity life, and sugary margaritas no more—the affluent, history-rich hometown of the University of Arizona has recently gotten a fresh perspective thanks to an influx of young creatives. Shop for minimalist apparel and accessories at the MSA Annex (a collection of 13 shops housed in shipping containers), dine on Central Mexican cuisine at Penca Restaurante downtown, and grab a light meal at Exo Roast Co., which uses local ingredients like barrel cactus jam and the cult favorite Barrio Bread. The award for most unique nightcap goes to The Owl’s Club, a hip, intimate cocktail bar located in a former funeral home.

21 Ultimate Road Trip Itineraries from San Diego

Amid all the new and cool, there are still the staples worth visiting, like Saguaro National Park, home to 25 varieties of cacti, including the namesake, which ranks as the tallest in the country, and Sabino Canyon, with its hiking trails, freshwater pools, and mini waterfalls. The retro-cool Hotel McCoy opened last summer with a pool and local art.

21 Ultimate Road Trip Itineraries from San Diego

And side trip alert! It’s worth detouring two hours north to Phoenix for the all-day eatery Roland’s Cafe Market Bar, a joint venture between award-winning pizza pro Chris Bianco and the duo behind Tacos Chiwas. While there, stay at Arizona Biltmore, a favorite among US presidents that just commemorated its 90th year with a $35 million renovation. Take a happy hour history tour of the 39-acre property with your choice of two tipples—like a tequila sunrise (first created at the resort) and a Catalina Spritz (Marilyn Monroe’s favorite to sip poolside).

Eastern Sierra

Why We Love It: It’s an underappreciated playground for outdoor enthusiasts

Fancy a road trip within a road trip? Venture north near Sequoia National Park and begin your drive along the 395, a gateway to some of California’s most photogenic natural wonders. You’ll start in Lone Pine, an Old West town that’s home to the impressive rock formations of Alabama Hills, where movies like 2013’s The Lone Ranger were filmed, as well as Mount Whitney.

21 Ultimate Road Trip Itineraries from San Diego

From there head an hour north to Bishop, known for its trout fishing and bouldering—there’s a women’s climbing event March 22–24. Great Basin Bakery is a homey, tasty option for bagels, sandwiches, pastries, and coffee. Making your way another hour north, bypass the tried-and-true Mammoth Lakes and opt for June Lake Loop. The landscape of the 15-mile drive looks straight out of the Swiss Alps, with plenty of cycling, fishing, and horseback riding to keep you busy. When you want to rest up, Double Eagle Resort & Spa is the winner, with comfortable cabins (pets allowed in some), a spa, and an indoor pool. If you want to trek even farther, head to Mono Lake, a serene, slightly spooky basin with boating and nature walks.

21 Ultimate Road Trip Itineraries from San Diego

Las Vegas

Sin City is more than just casinos, pulsating nightclubs, and restaurants that’ll shrink your wallet. Here’s a guide to the other side of Vegas—sparkly dresses and AmEx black cards not necessary.

Skip the Buffets—Dine Downtown

Located five miles from the flash of the Strip is a set of restaurants and cocktail bars that are much friendlier to your bank account. (And frankly, who needs a dozen types of pancakes before noon?) Try pies made by a 12-time pizza world champion at Pizza Rock or Asian-influenced chicken dishes at Flock & Fowl from James Beard–nominated, Joël Robuchon–trained chef Sheridan Su.

21 Ultimate Road Trip Itineraries from San Diego

Forget Club Hopping—Go Cocktail Bar Hopping

Instead of succumbing to bottle service, try the numerous zero-fuss bars around town, beginning with Herbs & Rye, a locally loved steakhouse with great happy hour deals. Then head north to Frankie’s Tiki Room for potent tropical tipples. When you cross east into the Arts District, the dimly lit Velveteen Rabbit will please everyone from cheap beer drinkers to cocktail connoisseurs. Finish the night at Atomic Liquors, a staple spot known for beer cocktails.

Don’t Walk the Strip—Stroll the Museums

Vegas culture goes beyond Lady Gaga concerts and Cirque du Soleil performances. At the Neon Museum, visit the Neon Boneyard, an alfresco collection of iconic neon signs collected from casinos, restaurants, and elsewhere. This fall, director Tim Burton will bring his original fine art to the space. The Mob Museum traces the history of organized crime in Las Vegas and throughout the country with hands-on forensic exhibits, preserved artifacts, and a working speakeasy and distillery to better explain the seedy side of the Prohibition era—and serve thirsty museum-goers.

21 Ultimate Road Trip Itineraries from San Diego

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8 Hours



Why We Love It: Newcomers are bucking the Napa traditions you used to know

You’ve ridden the wine train, dipped in the mud baths, and been denied a reservation at The French Laundry. Thanks to a crop of up-and-comers, Napa locales surrounded by old vines are finally keeping up with the times. On the northern tip of the region, Healdsburg’s Harmon Guest House, a boutique with 39 rooms, opened last fall; so did Vista Collina Resort on the southern end. The latter boasts "The Village," a lawn next to a food and wine center with cooking classes and nine tasting rooms, where you can even support San Diegan Tim Bacino at Gen7.

21 Ultimate Road Trip Itineraries from San Diego

Indulge in buttermilk fried chicken at Yountville’s Addendum, a counter-service offshoot of Ad Hoc (itself known for chef Thomas Keller’s simple prix fixe dinner), before beginning your tasting. Robert Mondavi and Grgich Hills are a good place to start. Purchase a Wine Priority Pass online to help pare down the rest of your reservations with deals like two-for-one tastings at select wineries. Ashes & Diamonds’ made-for-Instagram tasting room nails a midcentury-modern aesthetic as an homage to the era when wines really put the valley on the map.

21 Ultimate Road Trip Itineraries from San Diego

And while most of wine country calls it quits around 5 p.m., there’s the updated Villagio Bar & Lounge in Yountville and Sky & Vine Rooftop Bar atop the Archer Hotel in downtown Napa, both of which stay up late for the die-hard oenophiles.


Why We Love It: It’s one of the country’s most famous R&R spots for a reason

This pine-forest oasis in the scorching Southwest is famous among New Age and alt-medicine circles for its four "vortexes," said to be natural centers of earth energy and enlightenment. Start with a psychic reading and aura photo from Mystical Bazaar. At ChocolaTree, nourish your physical body with an organic, homemade, largely vegan menu with gluten-free and raw options. For affordable crystals and geodes, brave the tourist crowds downtown for Discount Gems & Minerals—and enjoy the public-use marimbas just outside.

21 Ultimate Road Trip Itineraries from San Diego

Marg’s Draw makes for an easy afternoon hike; or for a steeper trek, Cathedral Rock Trail brings you to one of the fabled vortexes. Once you’ve hit peak serenity, lay your head in one of Sky Ranch Lodge Resort’s private cabins with a back porch that opens up to stunning views of the red-rock-bluff valley.

San Francisco

Why We Love It: A new nonprofit restaurant is all the buzz

For 14 years, La Cocina has served as an incubator for food entrepreneurs in the saturated, uber-costly market of San Francisco. Their mission is to offer immigrant women and women of color affordable commercial kitchen space and technical assistance to build their businesses. So far, their efforts have helped launch several well-loved restaurants in the Bay Area: There’s the Lebanese-Syrian bakery Reem’s California and Cambodian Nyum Bai in Oakland, Southern food translated into sandwiches at Pinky & Red’s in Berkeley, and vegan tamales at Alicia’s Tamales Los Mayas in Hayward.

21 Ultimate Road Trip Itineraries from San Diego

This summer, the incubator will debut La Cocina Municipal Market in San Francisco’s ever-changing Tenderloin neighborhood to showcase the many small businesses they’ve fostered. In the same neighborhood, the Tilden Hotel’s minimalist design and suave in-house speakeasy are a welcome respite from the city’s hubbub. Hotel Emblem on the border between Nob Hill and Union Square just opened in January, paying tribute to the Beat Generation in decor and activities. They offer Meditation Hour every Saturday, a book butler program, and poetry slam nights, when guests are encouraged to take the stage.

21 Ultimate Road Trip Itineraries from San Diego


Pit Stop!

Pfeiffer Canyon Bridge, Big Sur’s crucial connection to the outside world, reopened after a mudslide closed it down for eight months in 2017. Many of the hotels—like Post Ranch Inn and Ventana Big Sur—used that time to execute multimillion-dollar renovations. (Hello, glamping tents!) To really take in the scene, sign up for the Big Sur Marathon, taking place April 28 along Highway 1. The highlight is the tuxedo-clad pianist playing on a baby grand along the Bixby Bridge.


21 Ultimate Road Trip Itineraries from San Diego

Pfeiffer Canyon Bridge

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National Treasures

There’s no time like the present to show some love for our national parks. Here are three road-trip-friendly excursions, plus one longer haul that’s worth every mile.


Grand Canyon

The Grand Canyon celebrates its 100th year as a national park in 2019 with events all year long. Highlights include the Centennial Summerfest and Star Party June 22–29 and a music festival August 25–26. The South Rim, a little over eight hours by car, offers that classic postcard landscape, but is also notoriously crowded. Opt for the more secluded North Rim, which is open after the snow melts from May to October and boasts vibrant foliage in the fall.

21 Ultimate Road Trip Itineraries from San Diego

You can make a home away from home with Under Canvas, a company that sets up glamping tents with a shower, sink, and flush toilet from late April to mid-November just outside the park in Valle, Arizona. (Their other locations include Yellowstone, Glacier, and Zion national parks, as well as Tucson, Mount Rushmore, Moab, and the Smoky Mountains.) After the arid areas, quench your visual thirst with a two-hour trip north to Lake Powell, a reservoir in Glen Canyon National Recreation Area that straddles the Arizona-Utah border, where you can swim, kayak, and hike.

21 Ultimate Road Trip Itineraries from San Diego


Eight hours from San Diego, Yosemite is all about the granite peaks and cliffs, especially El Capitan and Half Dome, which is why it’s such a draw for rock climbers. If you’re new to the sport or need a brush-up, REI’s Kearny Mesa store is hosting a Preparing for Half Dome class on March 2 with tips on gear, routes, and training. Otherwise, Half Dome’s summit is reachable on foot—if you’ve had a couple days to adjust to the altitude and start the 17-mile hike at the crack of dawn, that is.

21 Ultimate Road Trip Itineraries from San Diego

For an easier trail, seeing the supersize sequoias in Mariposa Grove is a must, and the park also offers a five-hour tour bus option departing from Yosemite Valley Lodge May through September. The Majestic Yosemite Hotel, formerly the Ahwahnee, is the quintessential stay, but if you want to get a taste without the triple-digit commitment, lunch in their grand dining room will give you the flavor.

For fun and inexpensive lodging minutes outside the park, stay in a yurt (sleeps four to six) at Yosemite Lakes RV Resort, complete with bathroom, kitchen, gas grill, and even cable TV.

Zion National Park

About eight hours from San Diego, Zion was Utah’s first national park—now there are five—and it has some of the state’s most famous trails. Check out the waterfalls of Emerald Pools, and The Narrows, a gorge with walls reaching thousands of feet high that requires "hiking" through a river. Or let someone else do the trekking for you: Local operators like Zion Ponderosa offer horseback riding trips into the park.

21 Ultimate Road Trip Itineraries from San Diego

When you want to rest those weary limbs, you can camp (Lava Point and Watchman are popular sites) or stay at the only in-park accommodation, Zion Lodge, in a cabin, hotel room, or suite surrounded by towering trees and red rock mountains.

Redwood National & State Parks

What a trip to the Redwoods costs in 800 miles worth of gas, it makes up for with the staggering sight of the world’s largest trees. The national park, which celebrated its 50th anniversary last year, is unlike many others in that there’s no entrance station or fee, and portions of it overlap with the state park, for which daily use fees apply.

21 Ultimate Road Trip Itineraries from San Diego

One of the best places to see the trees is the moderately challenging 4.2-mile James Irvine Trail in Prairie Creek Redwoods State Park, which ends at Fern Canyon, a lush area (albeit redwood-free) marked by a footbridge that’s open in summer months. Or hop back in the car and drive the steep 17 miles down Bald Hills Road to see old-growth redwoods, wildflowers in the spring, and if you’re lucky, Roosevelt elk.

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