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Why Southern California is The Perfect Backdrop for Remote Work and Adventure

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The rise of remote work has unlocked a new kind of freedom—the ability to trade your home office for almost any backdrop you can imagine. We recently went on a remote work trip/girls trip to Southern California. From bustling cities to charming beach towns, there’s something for everyone to enjoy! With its famous coastlines, towering mountains, and expansive deserts, outdoor enthusiasts will find endless opportunities, from surfing the Pacific Ocean to hiking through breathtaking landscapes. Don’t worry if you aren’t a fan of the outdoors! Southern California is also perfect for foodies and wine lovers.

This guide will walk you through a multi-stop journey across Southern California, from the rolling vineyards of Temecula to the desert oasis of Palm Springs. We’ll share our favorite spots to stay, eat, and explore, giving you all the inspiration you need to plan your own remote work adventure. Additionally, we’ll include some travel tips, such as how we utilized the Southwest Companion Pass to make this trip even more affordable. Ready to hit the road?

Getting There and Getting Around Southern California

We kicked off our Southern California tour by flying into San Diego International Airport (SAN), a hub for Alaska Airlines, Southwest Airlines, and Delta Air Lines. Although we didn’t spend any time in San Diego on this trip, we highly recommend spending some time there if you have the opportunity. A favorite of KarryAnne’s is the zoo!

We rented a car from the San Diego airport and headed out on our road trip. We traveled to Temecula, Big Bear, Joshua Tree, and finished our trip in Palm Springs, departing from Palm Springs International Airport (PSP). This one-way travel approach saved us time and enabled us to visit more places in Southern California.

A huge money-saver for this trip was the Southwest Companion Pass, which allows you to bring a companion for free (plus taxes and fees) on any Southwest flight. It’s a game-changer for anyone who travels frequently with a partner or friend. If you’re interested in earning a companion pass yourself, we think the quickest way to accumulate enough qualifying points is by using a Southwest credit card.

Stop 1: Temecula Wine Country

  • Wine tasting at Somerset Winery
  • Wines aged in terracotta pots
  • KarryAnne and Katie in Temecula
  • KarryAnne meets Taylor Swift the llama on a private sidecar winery tour through Temcula
  • Private sidecar tour through the vineyards of Temecula
  • View of the vineyard from our patio at Carter Estate Winery and Resort

    • Just an hour north of San Diego, Temecula Valley wine country feels like a world away. The unique microenvironment of Temecula, characterized by a Mediterranean climate, makes it Southern California’s premier wine region, boasting over 50 wineries set against a picturesque backdrop of hills. Temecula is also renowned for its excellent restaurants, championship golf courses, and hot air ballooning. We loved our time here so much that we plan to go back in the spring!

    Where to Stay

    We checked into the Carter Estate Winery and Resort, a beautiful property with spacious bungalows and private patios overlooking the vineyards. The resort also features a pool, which we enjoyed during a late-night dip, and our room included a giant tub for soaking in, which made unwinding after a day of exploring even more enjoyable.

    What to Do

    The best way to experience Temecula’s wineries is with a tour, and we can’t recommend the Private Sidecar Winery Tour enough. Zipping between vineyards in a vintage motorcycle sidecar is an unforgettable experience.

    Wineries We Loved

    • Somerset Vineyard & Winery: This spot has a cool, laid-back vibe. Be sure to try their unique wines aged in terracotta pots. Our favorite was the Le Meridio. They also have a delicious empanada stand at the entrance that you should definitely try!
    • Peltzer Winery: We visited during their annual pumpkin lighting, a festive event complete with free prosecco. This family-friendly winery has a pumpkin patch, a petting zoo, and live music on the night that we went.
    • Akash Winery: Our tour guide raved about their pizza, claiming it’s some of the best in the world. While we did try it, we were late picking it up, so we don’t think it’s fair to rate it yet.
    • Truffle Pig Craft Kitchen: While we didn’t eat here, the patio at their “Pig Pen” looked like a fantastic spot to relax with a glass of wine. We will definitely be trying to get a spot on our next trip!

    Downtown Temecula Eats

    For a great meal in Old Town Temecula, head to The Goat & Vine. Their “You Confit Me” pizza was incredible, and the Goat & Vine salad was fresh and flavorful.

    Stop 2: Big Bear Lake

  • The amazing cheese sticks!
  • Castle Rock Trail
  • The giant bathtub at Bluegreen Vacations Big Bear Village

    • After soaking up the sun in wine country, we headed for the mountains. Big Bear Lake is a year-round destination offering alpine scenery and a welcome escape from the city hustle. The area is also known for its mountain biking trails, making it a great destination for adventure seekers. A scenic bike ride around Big Bear Lake or along its forested paths is a great way to unwind and enjoy the natural surroundings.

    Where to Stay

    We stayed at Bluegreen Vacations Big Bear Village, which was ideal for our remote work setup. The spacious layout provided each of us with our own bedroom and workspace, and the fireplace created a cozy environment. Traveling from the heat of Houston, the cool, crisp air in Big Bear was a welcome retreat. The apartment had large windows in the living room that we opened to let in the fresh air. The highlight of this accommodation for KarryAnne was the large tub, which was perfect for soaking in. This accommodation is right next to the main street of town, where all the shops and restaurants are, making it ideal for popping out for a quick meal.

    What to Do

    Big Bear is a hiker’s paradise. We tackled the Castle Rock Trail, a 2.9-mile out-and-back route offering stunning panoramic views of the lake and surrounding forest. We didn’t have time to explore additional trails, but there seems to be a lot in the area. The area around Castle Rock also offers excellent rock climbing opportunities for those seeking more adventure.

    Where to Eat & Drink

    • Tropicali: This spot is highly rated as the #1-ranked restaurant in California on YELP and the #1-ranked poke restaurant in America. Don’t miss out on it! They also now offer Dole Whip, and you are going to want to try it. In addition to the delicious food, they offer a patio with a beautiful view of Big Bear Lake. However, there is no Wi-Fi, so please plan accordingly if you will be working remotely.
    • Murray’s Saloon & Eatery: If you’re looking for a fun night out, this is the place. The karaoke is lively, and the crowd is a blast. We highly recommend their cheese sticks! Just make sure to check the kitchen’s closing time, as we had to go back a second time to try this tasty snack, but it was worth it!
    • Whiskey Dave’s: A solid late-night option for drinks and dancing in the off-season. However, they are cash-only on weekends, so plan ahead.
    • Oakside: The fried green beans are a must-try appetizer.
    • Amangela’s Sandwich & Bagel House: A perfect spot for a quick and delicious lunch or a morning coffee, and one of the local coffee shops popular with both visitors and remote workers. We enjoyed sitting under an umbrella on their patio to get some work done while we waited to get our cheese sticks.
    • De La Nonna: We only stopped for drinks, but the stunning lake view from their patio is reason enough to visit, especially at sunset.

    Stop 3: Joshua Tree National Park

  • A Joshua tree
  • Joshua Tree Saloon
  • The view at the end of Hidden Valey Nature Trail

    • Next, we journeyed into the iconic desert landscape of Joshua Tree, one of the region’s most renowned national parks, attracting outdoor enthusiasts from around the world. The park’s stunning landscapes, with otherworldly terrain dotted with twisted trees and giant boulders, make it an ideal spot for adventure. This is a must-see for any Southern California road trip.

    Where to stay

    The Airbnb we stayed in was not ideal for remote work. While it had two bedrooms, the kitchen table was tiny, making it hard for two people to work on. However, our Airbnb did have a hot tub, which we highly recommend when staying in Joshua Tree! There is little light pollution in this area, so it is perfect for sitting in the hot tub and stargazing at night.

    What to Do

    We worked remotely from our Airbnb and took short evening hikes. With limited time, we focused on a couple of shorter, high-impact hikes:

    • North Canyon Trail: An easy 1.2-mile loop that gives you a great taste of the park’s beauty.
    • Hidden Valley Nature Trail: This popular 1-mile loop winds through a rock-enclosed valley and ends with a gorgeous view. This trail is more difficult and involves some rock climbing, so plan accordingly. Bring water and pay attention to the trail markers.

    Joshua Tree is also famous for its world-class rock climbing, attracting outdoor enthusiasts from around the globe. After your adventures, you’ll find plenty of cozy spots in and around Joshua Tree where you can relax or catch up on work.

    Where to Eat

    • Joshua Tree Saloon: This rustic, Western-themed spot is a local institution. We walked right in without a wait and enjoyed some tasty taquitos.
    • The Big Dez: A solid option for breakfast or lunch. They have a small patio area perfect for working remotely while you enjoy your meal.

    Stop 4: Palm Springs

  • The beef’n latkes at at Sherman’s Deli
  • The back patio at Koffi North
  • The pool at Desert Hills Hotel
  • Our room at Desert Hills Hotel

    • Our final stop was the desert playground of Palm Springs, known for its mid-century modern architecture, stylish resorts, and vibrant cultural scene. Palm Springs is a wonderful place with a thriving community that supports both work and leisure, making it especially attractive for remote workers.

    Where to Stay

    We loved our stay at the Desert Hills Hotel. The check-in process was seamless and done remotely-they simply texted us the codes to get into the hotel. The hotel was well-stocked with towels and even had a filtered water machine, which was a thoughtful touch. The hotel also has a decently sized pool if you want to cool off during the heat of the day.

    What to Do

    One of the best free activities in Palm Springs is simply driving around to admire the architecture. Don’t miss a drive-by of the Elvis Honeymoon Hideaway, a perfectly preserved example of the city’s mid-century charm. Unfortunately, the house is no longer open for tours. Exploring Palm Springs’ neighborhoods is also a great way to spend your free time between work sessions.

    Where to Eat

    • Sherman’s Deli & Bakery: A Palm Springs landmark, this New York-style deli was even featured on Diners, Drive-Ins and Dives. The BEEF’N LATKES sandwich is incredible, and the lemon bar is legendary—our waitress said it’s been her favorite dessert for 26 years.
    • Copley’s: An award-winning restaurant serving upscale American cuisine infused with traces of tropical and European flavors. Copley has been included in OpenTable’s “100 Most Romantic Restaurants in America” list for 2024, and the reasons are obvious. The outdoor patio with mountain views offers an ideal setting for date night! The crispy empanadas and pomegranate balsamic-glazed Scottish salmon were delicious!
    • The Tropicale Palm Springs: Bottomless mimosas! Do I need to say more? The brunch was decent, and they have a small TV at the bar if you want to catch a game.
    • Koffi North Palm Springs: Perfect place to enjoy a coffee on the tree-covered outdoor patio! It could be a great location for remote work.
    • Other Noteworthy Mentions: Our research pointed us to several Michelin-recommended spots, including Bar Cecil, 4 Saints, and Tac/Quila. Copley’s and Sandfish also came highly recommended.