Kimberly Jackson

Kimberly Jackson

Founder & Owner

A native San Diegan with over 12 years of real estate and management experience, Kim is dedicated to making the vacation rental process stress-free and financially beneficial for her clients. When she isn’t securing bookings, you can find this powerhouse single mom surfing with her three sons, boxing, or supporting local businesses.

We cannot believe it either. Labor Day weekend is almost upon us. This means we need to enjoy every minute of summer that we can. What better place to do this than in sunny Southern California? The coast is the ultimate destination if you are looking to spend your final summer days by the beach, visiting world-class attractions, or eating delicious seafood. Why not get a head start on your San Diego Labor Day weekend plans by considering the following activities? Find out how securing the right local accommodations can help you make the most of your long weekend away.

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Have Fun by the Coast at La Jolla Shores or Coronado Beach

With the summer season heading into fall, it is essential to spend as much time as you can on the beach. La Jolla Shores is a great option if you are planning family-friendly journeys across San Diego with your kids. The waves at La Jolla are less rough, and the shores are vast. The wide sand is perfect for running, playing catch, or renting boards for an afternoon of boogie boarding. You can also walk down to the nearby cove to watch the famous local seals sunbathe on the rocks.

There is also Coronado Beach, located near the iconic Hotel del Coronado with its red-topped roofs. This beach is great for spending the day relaxing in the sunshine, having a massive beach picnic, or walking along the shore as the water splashes your feet. You can spend hours at the tide pools searching for the unique creatures who live in the shallow waters of Coronado. Soak up every ounce of beach time during your Labor Day weekend in San Diego before the kids head back to school full-time.

[Guest Tip / Travel Pro]: Labor Day weekend is one of the busiest beach weekends of the entire year. Parking lots at La Jolla Shores and Coronado Beach often reach full capacity by 9:00 AM. Plan to arrive very early, or utilize rideshare apps to avoid the stress of hunting for parking.


View of the San Diego coastline

Marvel at the US Sand Sculpting Challenge

If you want to see something truly spectacular during your Labor Day trip, you must visit the US Sand Sculpting Challenge at the Broadway Pier. Master sculptors travel from all over the world to compete in this massive event. They spend days transforming hundreds of tons of sand into intricate, jaw-dropping works of temporary art right on the waterfront.

The event is much more than just a visual art show. The pier comes alive with live entertainment, dozens of local food trucks, and a dedicated kids zone where children can take lessons from professional sand sculptors. It is an incredibly unique way to spend a Saturday afternoon, and the photos you take of these massive temporary monuments will be the highlight of your vacation scrapbook.

Experience the Festival of Sail

Hosted by the Maritime Museum, the annual Festival of Sail is the largest tall ship festival on the West Coast, and it happens right over Labor Day weekend. The North Embarcadero transforms into a historic maritime village. You can walk the wooden decks of massive, restored sailing vessels that look like they sailed straight out of a pirate movie.

The festival offers actual sailing excursions where you can head out onto the bay aboard these historic ships. They even stage mock cannon battles on the water, which is incredibly loud and thrilling to watch. Between the ships, the beer garden, and the live music playing on the boardwalk, this event captures the true maritime spirit of the city.

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Savor the Flavor at Bayside Brews & BBQ

Plan to visit Bayside Brews and BBQ this long weekend, held through the first week of September at SeaWorld San Diego. You will not be able to contain your excitement when you see the huge selection of barbecue options paired with over sixty craft beers from local coastal breweries. You will be eating incredibly well in a beautiful location down by Mission Bay.

Try some smoked and grilled menu options while you listen to live music down at the exciting SeaWorld Park. Is there anything better than spending a weekend eating good food, tasting local IPAs, and soaking up the summer vibes? We think not. Add this event to your itinerary, and you will not regret it.

Celebrate California Wine Month at Local Wineries

September officially begins California Wine Month. Since Labor Day weekend rolls right into the start of the month, you will be well on your way to celebrating the grape harvest in Southern California. Head over to the heart of the local wine country at the vineyards of Ramona Valley. Or, opt for the scenic, rolling hills of the San Pasqual Valley.

These regions are known for producing heavy, delicious varietals like Viognier, Syrah, and Sangiovese. Savor the delicious summer harvest at Orfila Vineyards and Cordiano Winery, and sip a glass of wine while looking out over the valley. Escaping the busy coastal crowds to spend a quiet afternoon at a winery is the perfect way to recharge during a busy holiday trip.

[Guest Tip / Travel Pro]: Because Labor Day weekend is a massive tourist draw, securing dinner reservations at popular waterfront restaurants or winery tasting rooms is critical. Do not wait until the day of your trip to book your dining times!


Living space in one of our Del Mar weekend rentals

Stay in Comfort with Premium Accommodations

If you want to have a holiday trip of epic proportions, then you need to pick your accommodations wisely. Sure, it is easy to just pick a random hotel through a quick internet search. But why not give a little more care and thought to the experience you would like to have while celebrating Labor Day on the coast?

Vacation rentals managed by our local team can give you premium comfort, beautiful curb appeal, and extreme convenience. This helps your entire family feel completely at home the moment you arrive.

Would it not be nice settling into a home that is just a few steps away from the beach? This means you can wake up each morning and greet the ocean as you sip your cup of coffee. The ocean breezes help you wake up as you take in the view from your private balcony. With such an inspiring view, you cannot help but dream up all the things you are looking forward to doing over the long weekend.

Want to grill up some burgers after a day at La Jolla Shores or Coronado? Many of our coastal properties offer outdoor patios and private BBQs, perfect for grilling up goodness. Serve up the main course with some fresh sides prepared in the comfort of your full kitchen. After a day of sightseeing, experience the perk of going for an evening swim when you book rentals with private pools and hot tubs. Plan movie nights in the living room, quiet moments of solitude by the beach, or a great night’s sleep in your comfy master bedroom. If you own a home in the area and want to capitalize on this peak travel weekend, our expert property management team can help optimize your listing.

Book Your Labor Day Weekend Getaway Today

With these Labor Day weekend activities waiting for you, do not miss out on your opportunity to experience them. Warm weather, beautiful shores, and delicious beverages can be yours to close out the summer, but only if you get a head start and book your Del Mar weekend rentals today. If you need help finding the perfect property, you can always contact our local team for personalized guidance. Read more about Labor Day in San Diego County on our blog, reserve your stay today, and you will be ready to soak up the last bits of summer!

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Frequently Asked Questions About Labor Day Weekend

What is the weather like in San Diego during Labor Day weekend?

Late August and early September offer some of the warmest weather of the year. You can expect clear, sunny skies with coastal highs around 78°F to 82°F, making it perfect beach weather.

Is the water warm enough to swim during Labor Day?

Yes! By Labor Day weekend, the Pacific Ocean temperatures have peaked from months of summer sun. The water is generally around 68°F to 72°F, which is very comfortable for swimming and surfing without a wetsuit.

Do I need to buy tickets in advance for the US Sand Sculpting Challenge?

Yes. The sand sculpting event draws massive crowds to the Broadway Pier. Purchasing your tickets online prior to your arrival allows you to bypass the long entry lines at the gate.

How far in advance should I book my vacation rental for the holiday?

Labor Day weekend is the final major summer travel holiday. We highly recommend booking your coastal vacation rental at least three to four months in advance to ensure you get the best location and amenities.

What are the best family-friendly beaches for the long weekend?

La Jolla Shores, Coronado Beach, and Moonlight Beach in Encinitas are fantastic for families. They offer wide sandy areas, gentle waves, and full-time lifeguard supervision during the holiday weekend.