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

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

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

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

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.

Sometimes the most memorable vacations are the ones you never originally planned to take. Our recent getaway to Mexico started out as a major travel mishap. We completely missed our original flight to Fiji. Panic set in for a brief moment, but thankfully, a stash of Southwest points allowed us to pivot at the very last minute.

We traded the South Pacific for the Caribbean Sea and booked a spontaneous trip. This was our very first time visiting this vibrant Mexican destination, and we had to figure out the logistics on the fly. From navigating the busy airport to finding the best off-resort tacos, we learned a lot during our stay.

If you are planning your own tropical escape and want to know exactly what to expect, this travel guide covers everything from transportation and all-inclusive hotel dining to the excursions you absolutely cannot miss.

Introduction

Dreaming of turquoise waters, ancient Mayan ruins, and vibrant nightlife? Welcome to Cancun, a paradise on the Yucatán Peninsula that offers the perfect blend of relaxation and adventure. Whether you’re looking to unwind on pristine beaches or explore the ocean, this guide will help you plan an unforgettable trip. Ready to discover the best of Cancun? Let’s dive in!

Navigating the Cancun International Airport (CUN)

Getting off the plane at CUN brings a rush of excitement. The warm air hits you, and vacation mode officially begins. However, getting from the terminal to your hotel requires a bit of strategy.

The exit to the airport is notoriously chaotic. As soon as you walk through the final set of sliding doors, you enter what I call the “hall of vultures.” Dozens of transportation vendors will immediately approach you, offering rides and tours. Taxis are readily available here, but they are almost always the most expensive option. If you do find yourself needing a taxi, agree on a firm fare before you ever step foot inside the vehicle to avoid unexpected price hikes.

A much better approach is booking your transportation in advance. Shared shuttles are a highly popular, budget-friendly choice. Reliable companies like USA Transfers and Cancun Airport Transportation offer easy online booking. Just keep in mind that you will be sharing the ride, meaning you might have to sit through a few extra hotel stops before reaching your destination.

For a completely seamless start to your trip, a private transfer is the way to go. We booked a private ride with Cancun Shuttle, an official partner of the airport. Having a vehicle entirely to ourselves meant zero detours. We even received a welcome gift of a complimentary day trip for two, though our packed schedule meant we didn’t get a chance to use it.

Getting Around Town

Once you settle into your accommodation, you will likely want to explore beyond the resort grounds. We relied heavily on Uber for most of our transportation needs, and it worked out quite well during the day.

Late-night travel proved to be a different story. We visited during the week at the beginning of September. If we stayed out late, the available Uber drivers were simply too far away to make it practical. During those late-night outings, we ended up flagging down local taxis. Just remember to carry some cash and confirm the price upfront before hopping in.

Where to Stay

Choosing the right place to stay is key to your experience. The city is primarily divided into two main areas: the Hotel Zone (Zona Hotelera) and Downtown Cancun (El Centro). 

• The Hotel Zone (Zona Hotelera): The Hotel Zone is a 14-mile-long island strip that is home to Cancun’s most famous all-inclusive resorts, stunning beaches, and high-end restaurants. If your idea of a perfect vacation involves waking up to ocean views, lounging by an infinity pool, and having everything at your fingertips, this is the place for you. It’s also where you’ll find the best nightlife and shopping centers like La Isla Shopping Village.
• Downtown Cancun (El Centro): For a more authentic and budget-friendly stay, consider Downtown Cancun. Here, you’ll find smaller boutique hotels, bustling local markets, and incredible street food. Staying in El Centro gives you a taste of local life and is a great base for exploring beyond the tourist trail. It’s a short bus or taxi ride away from the beaches of the Hotel Zone, so you can still enjoy the sun and sand.

Where We Stayed: Hotel NYX Cancun

We spent our vacation at the Hotel NYX Cancun, a 3.5-star all-inclusive property sitting right on the white sand.

We visited during sargassum season, a time of year when seaweed frequently washes up on Caribbean shores. The hotel staff did an impressive job managing it. The beach was consistently clear throughout the morning and early afternoon, leaving us plenty of time to enjoy the ocean.

One notable drawback of the hotel was the outdoor pool. It was heated, which made it far too warm to enjoy during the hot daytime hours. We preferred cooling off in the ocean instead.

The staff at Hotel NYX truly shone in hospitality. Without us even mentioning it, they realized it was my boyfriend’s birthday. We returned to our room to find it fully decorated, complete with a birthday cake and a chilled bottle of Prosecco. It was an incredibly thoughtful touch that made the stay memorable.

All-Inclusive Dining at Hotel NYX

A major benefit of this budget-friendly hotel was its all-inclusive features. While we usually like to try local foods, it was convenient to enjoy free drinks and snacks anytime we desired. 

• Chianti Restaurant: This traditional Italian spot was easily our favorite restaurant on the property. For every three nights of your all-inclusive stay, you receive one complimentary dinner at the restaurant. However, you do need to make a reservation in advance. Earning a 2023 TripAdvisor Travelers’ Choice Award, Chianti consistently serves up high-quality dishes and excellent wines.
• Umami: If you crave Asian cuisine, Umami offers a sushi bar and a teppanyaki table. You do not need a reservation for the sushi bar, but the teppanyaki experience requires prior booking and a minimum stay of five nights on the all-inclusive plan. We didn’t stay quite long enough to try the teppanyaki, but it always looked lively and popular.
• Deck: For a casual meal with an unbeatable view, Deck serves both lunch and dinner right along the oceanfront.
• Lobby Bar: This is your only late-night drinking option on the resort. Take their dress code seriously. We tried to grab a drink, wearing tank tops and bathing suits, and were promptly turned away.
• Magic Bar: Located right by the pool, this bar keeps the daytime drinks flowing. While I wasn’t a fan of many of the signature cocktails on their standard menu, I quickly discovered they happily make off-menu mimosas.
• Beach Service: You rarely have to leave your lounge chair. Attentive servers walk up and down the beach taking food and drink orders while you soak up the sun.

The Best Restaurants in Cancun

Exploring the local culinary scene is essential. We left the resort multiple times to experience various restaurants, from affordable tacos to fine dining.

• Tacos Villanos: Located conveniently right next to Hotel NYX, this is an absolute gem. Do not skip this spot. The tacos are loaded with flavor, deeply authentic, and perfect for a quick dinner or late-night snack.
• El Galeon de Cariba: For a laid-back, authentic experience, head to El Galeon de Cariba. They serve fantastic fresh seafood and cheap, ice-cold beer. Just remember to hit an ATM first, as they operate strictly on a cash-only basis.
• Navios: We wanted a nice dinner environment without an inflated hotel price tag, and Navios fit the bill perfectly. You sit on a lovely wooden deck suspended right over the water. A major word of caution: the mosquitoes are relentless. We were attacked the entire evening, and our bug spray did absolutely nothing to deter them. Dress accordingly.
• Mochomos: Mochomos offers a chic, modern atmosphere and incredible craft cocktails. My boyfriend thought they made the best carajillo on the island. They also surprised him with a beautiful dessert to celebrate his birthday.
• Ilios Greek Estiatorio: For dinner and a show, Ilios is the place to be. Located in the Hotel Zone, this upscale Greek restaurant provides a massive entertainment factor featuring belly dancers and spectacular fire shows. The food holds up to the hype, and I absolutely loved their gyritos.

Top Activities and Excursions

Cancun offers premier tropical ocean experiences, with vibrant marine life that attracts snorkelers from around the world. Snorkelers can explore colorful coral reefs, nearby islands, and unique underwater attractions. One highlight is the Cancun Underwater Museum (MUSA), which features over 500 life-sized sculptures designed to promote coral reef growth. During the summer months from June to September, you can join bioluminescence tours in Nichupté Lagoon for a magical nighttime experience. For adventure seekers, eco-parks like Xtreme Park offer ziplining and swimming in underground rivers. If you want to see videos of us exploring the underwater world, head over to our YouTube channel at Sips and Strange Places.

Snorkeling the Reefs and MUSA

We booked a comprehensive two-and-a-half-hour excursion with Total Snorkel Cancun. The tour packed a massive amount of sightseeing into a short window. We swam alongside majestic sea turtles, explored coral reefs, and floated over a sunken shipwreck.

A major highlight was visiting MUSA, the Underwater Museum of Art. Seeing the hauntingly beautiful underwater statues, especially the giant hands, is a surreal experience. We also explored an underwater cenote. Snorkeling requires less effort than scuba diving and requires no special training, so anyone can join in.

If you are new to snorkeling, no worries! This tour has everyone practice in shallow waters before heading out to sea, making it accessible for beginners. For equipment, there is no need to bring your own diving mask or fins, as the tour provides all equipment. They also have waterproof cameras and will take pictures of you exploring the underwater world for a nominal charge. However, I do recommend bringing a hat and sunscreen!

Here is the exact tour we took: 5-in-1 Cancun Snorkeling: Turtles, Reef, Musa, Shipwreck, Cenote

You can watch footage of us swimming with sea turtles and exploring underwater statues right here on our YouTube channel.

Swimming with Whale Sharks

This excursion was the highlight of our trip. With so many operators offering whale shark tours, selecting the right one was overwhelming. We paid a slightly higher price for our specific tour, and it was worth every penny. It was fully all-inclusive, meaning we enjoyed food and a floating bar without feeling nickel-and-dimed at every turn.

Timing is a key factor in booking this tour. The official whale shark season concluded on September 17 in 2025, and since we visited in early September, the tour company couldn’t promise a sighting. The trip’s success relies on unpredictable factors such as wind, sea conditions, food availability, and lunar phases. It’s recommended to provide the tour company with a range of possible days so they can select the optimal window.

I previously went on a whale shark tour in Cabo, and it was a miserable experience. The visibility was almost zero. The operators allowed dozens of people to jump into the water simultaneously, causing total chaos. We kept dodging other boats, and I only saw the spots of a whale shark when it was mere inches from my face, forcing me to frantically paddle backward to avoid a collision.

Our Cancun tour was the exact opposite. They launch later in the morning than other companies, which means you avoid the massive crowds of boats. Better yet, they only let passengers jump into the water in pairs. We had the space and peace to swim right alongside these gentle giants without fighting for a view.

Whale sharks are the biggest fish in the world, reaching an average length of 25-40 feet (and a weight of about 46,000 lb. Their large mouth, located at the front of their head, allows them to feed by filter-feeding on plankton, small fish, and fish eggs near the surface. Their distinctive white spots and pale grey skin cover their body, making each animal unique and allowing researchers to identify individuals. Whale sharks are highly migratory, traveling vast distances across tropical oceans, including the Atlantic Ocean and Indian Ocean, and can be found in oceanic waters, open waters, and sometimes near the coast and shore. One of the most famous whale shark gatherings happens off Mexico’s coast, especially near the Yucatán Peninsula, Holbox, and Isla Mujeres. Each year, from May to September, hundreds of whale sharks congregate in these waters to feed on plankton and fish spawn. Satellite tags have revealed that many of these sharks migrate long distances, with some crossing the Gulf of Mexico to reach these feeding sites.

As an endangered species, they are declining in population due to threats such as fishing and bycatch. Conservationists use satellite tags to track their movements and study their habitats. Whale sharks pose no threat to humans or divers, and responsible tourism is vital to protect these amazing animals.

Here is the exact tour company we used: Underwater Mexico.

Check out our full whale shark adventure on our YouTube channel here.

Take a Day Trip to Isla Mujeres

If you have an extra day, you can take the ferry to Isla Mujeres. The island has a more laid-back, relaxed atmosphere than the busy Hotel Zone, with beautiful beaches and numerous golf carts available for rent to explore the area.

Frequently Asked Questions

When is the best time to see whale sharks in Mexico?
The season typically runs from mid-May to mid-September. July and August are generally considered the peak months for guaranteed sightings.

What is sargassum, and when does it happen?
Sargassum is a type of brown seaweed that periodically washes ashore. The season usually peaks between April and August, though resorts work daily to clear the beaches for their guests.

Did you try and like Coco Bongo’s?
We did go there for about 20 minutes. It was absolutely not for us. Watered-down drinks and packed in like sardines.

Start Planning Your Getaway

Our accidental trip turned out to be an unforgettable adventure. From indulging in rich Italian dinners at Hotel NYX to swimming with whale sharks in the open ocean, Cancun delivers a dynamic mix of luxury and thrill.

Pre-book your airport shuttle, prepare for the mosquitoes if you dine on the water, and definitely pay a bit extra for a reputable snorkeling or boat tour. It makes a world of difference.