This is a guest post by Ava Bennett, a California-based travel writer who specializes in coastal getaways and weekend escapes. She’s spent years uncovering the best hidden beaches, scenic trails, and local eats along the West Coast.
There’s something effortlessly relaxing about San Diego’s coastline. Maybe it’s the way the sun slips slowly into the Pacific each evening. Or maybe it’s the mix of laid-back beach towns and world-class dining that makes the area feel both casual and special — the kind of place where flip-flops and fine wine coexist.
If you’re craving a weekend that blends nature, culture, and a bit of indulgence, we’ve got just the itinerary for you. San Diego’s coastline delivers it all — from oceanfront trails and dramatic cliffs to eclectic neighborhoods and incredible food. La Jolla, one of the city’s most scenic spots, makes a perfect starting point. This two-day escape will take you from sea caves and sunset views to surf towns and relaxed dinners, all with that unmistakable coastal California charm. Let’s dive in.
Morning Magic at La Jolla Cove
Start your weekend with a slow stroll along the shoreline at La Jolla Cove — one of San Diego’s most iconic spots. Early mornings here are peaceful, with just the sound of waves crashing against the rocks and sea lions barking from their sunbathing spots.
Walk the paved Coast Walk Trail, a gentle path that winds above the water and offers sweeping views of the Pacific. Along the way, you might spot pelicans gliding over the surf or kayakers exploring the caves below. If you’re feeling adventurous, book a guided snorkel or kayak tour to explore the underwater world of the La Jolla Ecological Reserve.
Not in a hurry? Spend some time at Shell Beach or Boomer Beach, watching tide pools reveal tiny marine life at low tide. These quiet moments by the water set the tone for the relaxed weekend ahead.
Strolling, Shopping & Seafood in the Village
After your morning by the water, head into La Jolla Village — a charming downtown filled with boutiques, cafés, and ocean-view restaurants. Whether you’re in the mood to shop or simply wander, there’s something to explore on every corner.
Some suggestions for your afternoon:
- Grab lunch at George’s at the Cove for rooftop views and California cuisine, or try Café Milano for a cozy Italian option
- Browse local shops for beachwear, art, or handcrafted souvenirs
- Stop by the Museum of Contemporary Art San Diego for a dose of culture with a coastal backdrop
If you’re traveling with kids (or just curious), the Birch Aquarium at Scripps is a short drive away and offers a fascinating look into marine life and ocean science.
Golden Hour Views & Oceanfront Dining
Evenings are pure magic along the coast, and La Jolla offers some of the best sunset points around. Consider heading to Mount Soledad, where panoramic views stretch across the entire San Diego coastline. Or, for a more intimate experience, visit Windansea Beach, a favorite among locals for its natural rock formations and pink-hued skies.
Once the sun has dipped below the horizon, settle in for a relaxed dinner. For oceanfront ambiance, Duke’s La Jolla or The Marine Room offer coastal fare with unbeatable views — and you’ll often hear waves crashing just below your table.
Coastal Trails & Clifftop Breezes at Torrey Pines
Start Day 2 with a short coastal drive to Torrey Pines State Natural Reserve, one of San Diego’s most scenic outdoor spots. Rising above the coastline, the reserve is home to trails that combine ocean views with breezy, easygoing hikes.
The Guy Fleming Trail is a great choice for a short walk with epic ocean views and seasonal wildflowers. If you’re up for something a bit more challenging, the Beach Trail takes you down to the sand — just be ready for the climb back up.
Don’t rush. The sea breeze, the smell of chaparral, and the views from the cliffs are all part of the experience.
Choose Your Vibe: Surf Town or Boho Beach Scene
For the afternoon, you’ve got two great options depending on your mood:
Option A: Encinitas
Head north to Encinitas, a mellow surf town with a creative vibe. Stroll through the San Diego Botanic Garden, grab a smoothie at Better Buzz, or visit the Self-Realization Fellowship Meditation Gardens, which overlook the ocean and offer a rare moment of stillness.
Option B: Ocean Beach
Or go south to Ocean Beach, known for its retro charm, quirky shops, and friendly locals. Walk the OB Pier, browse vintage thrift stores, and try a burrito from Hodad’s — messy, massive, and totally worth it.
It’s all part of what makes the San Diego area so fun to explore — no two beach towns feel quite the same.
A Sunset Farewell to the Weekend
End your weekend with a sunset stop that feels a little different from the beach.
Cabrillo National Monument, located at the tip of the Point Loma peninsula, offers one of the highest coastal viewpoints in San Diego. From here, you’ll see the Pacific Ocean on one side and sweeping views of San Diego Bay, Coronado Island, and the downtown skyline on the other. Plan to arrive before 5 p.m., as the park closes at sunset, and give yourself time to walk to the cliffs or visit the historic lighthouse before the sky starts to glow.
For an easier, no-entry-fee option, head to Harbor Island, just across the water from downtown. This narrow strip of land has benches, grassy areas, and uninterrupted views of the skyline and marina. It’s a peaceful, low-key spot to grab takeout, watch sailboats drift by, and see the city light up as the sun sets behind Point Loma.
Before You Go: Tips and a Thoughtful Finish
A few things to keep in mind as you plan your San Diego weekend:
- Pack layers – Even sunny days can turn cool in the evenings along the coast
- Book dinner reservations early – Especially for ocean-view spots on weekends
- Start early when possible – Morning light is beautiful, and you’ll beat the crowds
- Don’t skip the sunsets – Try to catch one from a different spot each evening
If you’re not in the mood to deal with traffic or parking near busy beaches, using a chauffeured service for your trip can make getting around feel much more relaxed. It’s also a convenient way to move between coastal towns and scenic spots without the hassle of driving or navigating unfamiliar roads.
Whether you’re coming from nearby or flying into San Diego International Airport, the coast delivers a perfect blend of nature, food, and laid-back charm. It’s the kind of weekend that leaves you feeling lighter — just like the ocean breeze.
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