California Coast Road Trip with Grandkids: Ultimate Skip-Generation Adventure

Children’s Pool Beach in La Jolla was our first introduction to sea life in their natural habitat. A few dozen sea lions were basking in the sun on the other side of the jetty.  ©Dawn Damico

Destination: California / A California Coast road trip with grandkids

“Nona, we have to go back. The splash didn’t get me!”

My strategy of sitting just beyond the splash zone backfired. The clever girl quickly realized that we were in the “wrong” seats.

This summer, I packed up my five-year-old granddaughter and set off on a California adventure that transformed an ordinary summer into a magical quest of discovery.

We started with orcas performing at SeaWorld, proceeded to sea lions and elephant seals lounging on California’s golden sands, sprinkled in beach picnics and coastal hikes, sipped on grapes (both fermented and not), roamed with dinosaurs, discovered the Pacific’s underwater world, and topped it off with wild whale and shark sightings.

If you’ve ever considered traveling with grandkids through multi-generational or skip-generation travel, do it. I cannot think of a better way to break up summer “doldrums.” 

Traveling with your grandchildren lets you see the world through their eyes. It forces you to slow down and embrace the thrill of rediscovery while providing a unique opportunity to influence how they interact with the world. Done right, the experience enriches all generations, creating memories that deepen relationships and add life to your legacy.

Why California? A Natural Playground

Our trip aligned with a family gathering which we extended by driving up the California Coast. Having lived in both Southern and Northern California, I appreciate that my two favorite landscapes – beaches and mountains – sit so close to each other. Add in the rocky cliffs along the central and northern coasts, and you have an outdoor wonderland that naturally tempts every inner adventurer.

Our journey from San Diego to Monterey created memories that will last a lifetime, for both of us. This skip-generation travel itinerary along California’s coast delivers the perfect blend of education, adventure, and pure joy.

The “Nat” provided hours of entertainment with five floors of discovery. Located at Balboa Park, you can ride a vintage carousel and enjoy acres of greenspace and cultural venues.  ©Dawn Damico

San Diego launched our California Coast roadtrip with grandkids adventure. We spent four days exploring the city, staying at the SpringHill Suites near Scripps. This proved to be a smart choice, positioning us between La Jolla’s upscale charm and downtown’s vibrant energy.

The San Diego Natural History Museum in Balboa Park was a surprising discovery. It’s a 1200-acre wonderland for children and adults. Wide paths are perfect for little legs with plenty of space to run and explore. The vintage carousel is a touchstone from a bygone era while historic architecture, remnants of the 1915 Panama-California Exposition, gives European-inspired elegance to various cultural venues. 

The museum’s interactive exhibits sparked my granddaughter’s curiosity about the natural world—a theme that continued throughout our trip. Five levels of exploration kept us engaged for several hours.

SeaWorld offered a classic San Diego theme park experience, but La Jolla’s Children’s Pool Beach stole our hearts. Picture this: standing on a jetty with Pacific waves crashing on one side while observing seals lounging peacefully on the sand of a protected beach just feet away.

This was our first glimpse of sea life in their natural habitat. Not in a book. Not in a zoo. But in the wild. The sense of wonder and magic reflected in those little eyes was priceless.

Dining Highlights: 

Puesto in La Jolla: fresh tacos and cold beverages enjoyed by both adults and little ones

Yanni’s Bar & Grill: dinner conveniently located right next to our hotel

*see map below

Temecula wine tasting is always a good idea. Each winery we visited had something interesting for the whole family.  ©Dawn Damico

An hour inland from San Diego, Temecula wine country proved that vineyards can absolutely be family-friendly! Rolling hills from California’s Inland Empire and vineyard views provide a scenic change of pace from the coastal environment.

Doffo Winery provided an unexpected treasure: a collection of vintage motorcycles displayed alongside stacks of wine barrels, a reference to the owner’s love of racing. While we enjoyed wine tasting, our granddaughter was fascinated by the gleaming bikes. After careful consideration, she chose “the red one” as her favorite, only because she didn’t see a pink one.

Lorimar Winery was family-friendly wine tasting at its best. The live music and expansive outdoor patio allowed for lunch with extended family in a festive and casual atmosphere. After eating, we took a short stroll to a garden area strategically tucked next to the vineyard where family conversations continued while the kids explored the grounds. Thoughtful touches like this make certain wineries standout destinations for multi-generational groups traveling with kids.

Pro Tip: We stopped in Temecula for the afternoon on our way to a family event. However, if you are planning a similar itinerary, I recommend staying overnight in Temecula before continuing. You can safely enjoy any of almost 50 wineries without driving concerns.

South Orange County has many family-friendly beaches. With another day we could have visited the Ocean Institute in Dana Point Harbor or hopped a ferry to Catalina Island.  ©Dawn Damico

A single day in San Clemente, our former home, brought back a lot of memories. And  sharing it with our family proved that simple experiences create lasting memories. 

The Surfbreak Hotel, recently acquired by new owners who have done a beautiful job upgrading it, has large, comfortable rooms and a great location. The donut shop across the street was a fun morning treat for my granddaughter. It never ceases to amaze how a few rainbow sprinkles can add a little sunshine to any morning, even when it’s covered with a blanket of what we call June-gloom.

The iconic pier at San Clemente Beach had everything we needed for a perfect beach day. The playground swings right on the sand were a hit, as were the Amtrak trains passing by. A scoop of ice cream from the beach-front shop across the tracks solidified that our summer vacation had officially begun.

As the day wound down, we picked up a bottle of wine and food from the nearby Chick-fil-A (sometimes practical trumps fancy on family trips) and headed to Dana Point Harbor for a sunset picnic. While the weather was a bit cool (okay, cold!) and windy, watching dusk settle over the water with family was a perfect travel moment.

Santa Barbara has miles of hiking paths, an urban wine trail, and beaches, parks, and museums to ignite a love for nature.  ©Dawn Damico

Santa Barbara claimed the next four days of our journey. We based ourselves at the sophisticated Drift Santa Barbara, a member of Design Hotels. While the modern and minimal rooms with mostly one-bed layouts cater more to solo and couples travelers than families, it is a lovely hotel I would happily choose again. The perfect balance of style and comfort, ground-floor coffee and cocktails bars, and easy access to  city attractions are a big plus. We booked their “small” room with a double bed, fine for our needs, and my granddaughter loved the rainfall shower.

Vendors were setting up at the evening farmers market on State Street when we arrived, one of many weekly evening markets in the area. We purchased nuts and dried fruit for our road trip before grabbing a slice of pizza for dinner. 

The Santa Barbara Museum of Natural History Sea Center became an instant favorite. Touch pools encourage safe interaction with sea creatures, although my granddaughter determined that petting manta rays would have to wait until she turned six. The octopus tank mesmerized us both and the Channel Islands sea life exhibit added educational value to our coastal adventure.

I purchased a yearly membership at this location rather than single tickets. This granted us free access to the main museum and reciprocal benefits with a network of museums nationwide, including several near our home.

Stearns Wharf is unlike pedestrian-only piers because cars can travel over bumpy wooden planks to reach restaurants and the Sea Center located at the end of the pier. We watched fishermen cast their lines, summer sailors learn to navigate their sails, and scanned the horizon for whale spray and sea lions.

The main Santa Barbara Museum of Natural History immediately captured our attention when “Chad,” the blue whale skeleton, welcomed us at the entrance. But it was the dinosaur park with moving dinosaurs that truly thrilled my granddaughter. The butterfly garden, land and sea exhibits, and outdoor backyard play area kept us busy for hours.

After the museum, we picked up picnic supplies and locally produced wine at the grocery store before heading to Butterfly Beach in Montecito. We found a protected area behind sun-warmed rocks to enjoy the sunset. Our conversation flowed as easily as the rhythm of the surf while the sun transitioned our souls from day to night.

Dining Highlights

The Cruisery: bicycle-themed decor and a doggie flight of water dishes on the outdoor patio, was a great choice for dinner of salmon and sweet potato salad

Scarlett Begonia: brunch and friendly servers who gave us some great ideas for enjoying the town

Staying in San Luis Obispo proved ideal to enjoy the sunny side of wine country, and the coastal charm of Pismo Beach. Be sure to get a bowl of clam chowder when you’re at the pier and ship a couple of bottles of wine home.  ©Dawn Damico

Two days in San Luis Obispo broke up the drive time between Santa Barbara and Monterey, giving us an opportunity to explore wine country and Pismo Beach. 

The newly opened Residence Inn by Marriott (opened in April 2025) offered spacious, comfortable accommodations, a beautiful pool area, and convenient laundry facilities should you need them.

Pismo Beach

Our route from Santa Barbara included a scenic stop at Pismo Beach Pier. The playground at the pier allowed little ones to run off energy after the drive while The Splash Cafe’s fully-loaded clam chowder served in a sourdough bowl is now my gold standard. The line out the door and down the street hints at the iconic cafe’s reputation. This was my granddaughter’s first chowder experience – other clam chowders don’t have a chance!

The SLO Ranch Farms and Market, conveniently located next to our hotel, is a destination in itself. This multi-venue complex offers restaurants, markets, live music, and games—something for every member of your group.

SLO Wine Trail

Wine tastings at Claiborne & Churchill and Saucelito Canyon showed us that San Luis Obispo’s wine scene rivals more famous regions. While I enjoyed the tastings, my granddaughter had her own grape experience (the juice kind, in a box). Both wineries have beautiful outdoor seating in vineyard settings that allowed her to wander where it wasn’t too busy. Both wineries shipped purchases home – essential for traveling families.

A Little Bit of Country

Avila Valley Barn scored high marks for their pie and petting zoo. We bought romaine lettuce from their produce market so my granddaughter could feed the animals. Yes, there were goats (to my delight). While the animals enjoyed lettuce, we grabbed snacks for Dinosaur Caves Park in Pismo Beach. Fast friends were made at the large neighborhood playground overlooking the beach as sunset created the perfect ending to our San Luis Obispo experience.

The Rookery is near San Simeon’s Hearst Castle. If Hwy 1 is closed, you can take Hwy 46 inland to the 101 which brings you past several Paso Robles area wineries.  ©Dawn Damico

Monterey marked the northernmost point of our itinerary with signature morning fog and cool temperatures that felt more like perfect spring days. As grey mornings turned to sparkling blue and emerald greens, the city revealed its natural beauty and bounty that has drawn man and beast to this region for millennia.

Taking Advantage of the Road to Monterey

Our drive from San Luis Obispo included two unique stops that showcase California’s coastal magic. Piedras Blancas Rookery is home to elephant seals basking on the beach and play-fighting in the water. Walkways above provide safe viewing points to observe these sea mammals natural behavior. I got a kick from watching a male elephant seal’s rejected attempt to woo a female, while my granddaughter giggled at their barking and snorting—a wildlife experience that rivaled any zoo visit and reminded her of “papa’s snoring.”

Next, we drove to Limekiln State Park along Highway 1 toward Monterey. Stunning coastal scenery and multiple lookout stops will compete for your attention as you navigate winding roads along steep cliffs. 

Tip: Check Highway 1 conditions before traveling—rock slides frequently close sections. We learned this lesson when road closure signs forced an hour-long detour as we backtracked to a main road. Poor cell reception at the park prevented us from checking if partial road openings existed (which they did).

We Arrived!

We arrived in Monterey just in time for the evening farmers market. The Marriott Monterey served us well for three nights. Its location on Calle Principal placed us right in the heart of California history. The street is lined with National Historic Landmarks that represent the district’s stronghold of European civilization on the American Pacific Coast from 1770 to 1849. Every walk through streets and alleyways felt like traveling through living history.

My granddaughter enjoyed her first trolley ride. The MST system operates free service from Memorial Day through Labor Day, connecting Downtown Monterey, Fisherman’s Wharf, Cannery Row, and the Monterey Bay Aquarium throughout the day. 

The world-class Monterey Bay Aquarium didn’t disappoint. The area around the Old Fisherman’s Wharf is a little touristy and can get crowded so using the trolly to get there is a great idea.  ©Dawn Damico

​The Monterey Bay Aquarium

The Monterey Bay Aquarium lived up to its world-class reputation. Even having visited before, exhibits amazed me as underwater worlds revealed themselves through layers of shadow, light, and color. We took our time as my granddaughter’s curiosity and wonder unfolded. I loved the opportunity to introduce her to the ocean’s abundance, diversity, and beauty that has brought me a lifetime of happy memories.

Tip: We purchased a snack while waiting for the sea otter demonstration; however, others brought light snacks – a more economical decision considering the aquarium’s premium food pricing.

Strolling along the Old Fisherman’s Wharf allowed souvenir shopping for a few small stickers to add to our travel journal. While the food at our waterfront restaurant was merely adequate, the panoramic 180-degree view was incredible. We even spotted a whale in the distance, which sparked a conversation about the phrase “thar she blows!” as we watched for breaching bodies and awe-inspiring views of a large tail diving into the ocean. This unexpected wildlife encounter perfectly capped our ocean-themed day.

Alta Bakery had a line out the door every morning we were there. These sandwiches were just being brought out as we were ready to leave…perfect timing for gathering provisions for our picnic lunch later in the day.  ©Dawn Damico

17 Miles to Point Lobos

After a morning stop at Alta Bakery and Cafe for coffee, pastries, and sandwiches for later, we headed to the famous Pebble Beach Links and 17-Mile Drive. Don’t be fooled, 17 miles will take you more than 17 minutes to complete. 

Scenic beauty around every corner includes multiple marked stops including the iconic Lone Cypress and Pescadero Point, plus unmarked discoveries from the middle of the road like spotting a buck through morning fog as he enjoys breakfast along the coast.

Tip: I considered an electric bike ride for the 17-Mile Drive and the outfitters I researched have options to accommodate kids. Perhaps a future trip!

We emerged from the drive and headed to Point Lobos State Natural Reserve. Our timing for Weston Beach tide pool exploration during low tide was off, so what we saw was limited to some tiny crabs and large rocks to climb on. 

However, binoculars borrowed from the visitor center allowed my granddaughter to scan the horizons for whale spray and zoom in on thousands of birds congregating on offshore rock formations. 

To wrap up the day, Dennis the Menace Playground near downtown Monterey provided fast friends and faster feet. A bit of ice cream from Revival Ice Cream shop was the perfect sweet ending to our Monterey days.

Traveling at the pace of a child means stopping to look at things we may otherwise pass by. Talking about the day’s plan every morning, and ending the day with time in a pool or playground resulted in a hassle-free experience.  ©Dawn Damico

To break up the long drive to Southern California, we made an overnight stop in Costa Mesa for dinner at Maggiano’s, a dip in the pool, and a good night’s sleep before our last night in San Diego. The Westin San Diego Bayview offers excellent downtown walking access and free shuttle service to the airport.

Seaport Village

We walked to Seaport Village, which has several dozen shops and restaurants, a koi pond retreat where baby ducks delighted us as they built their swimming skills, wine tasting venues, and ice cream shops. Some believe that Seaport Village sits on darker historical ground, Punta de los Muertos (Point of the Dead). There is even a historical marker explaining the circumstances. However, sometimes new information emerges that questions long-held assumptions.

According to at least one source, the “dead men” referenced in historical documents may not refer to sailors dying of scurvy, but instead to “dead” logs buried in the harbor to anchor ships. 

No matter what truth lies buried in the harbor, today hundreds of people enjoy the 14-acre waterfront park every evening. They sit on park benches to watch kite flyers and the setting sun or stroll along brick-paved walkways extending for miles along San Diego’s shores.

This was the final stop of our California Adventure. The warm sunset breeze perfectly capped off our journey as we talked about what we liked best, and where we should go next.

Before our journey, we watched some movies about sea life on the California Coast. Then, when we saw everything in the wild, ‘Little One’ felt as if she knew something about it. She seemed inspired to watch closely to see if it was just like the movies and observe when might be new or different.  ©Dawn Damico

All in all, the itinerary worked well though I’d consider small adjustments: a San Francisco return flight rather than a two-day drive back to San Diego, warmer-month glamping options, or adding in a few more coastal treasures. A Channel Islands day trip—we camped there overnight when my daughter was young—didn’t work this time but awaits future adventures.

Travel always offers more to see and do. What I’ve learned, especially when traveling with kids, is to have a plan, then plan to adjust that plan based on what unfolds during the trip. 

During the planning phase, I chose a few key destinations: The Natural History Museums, the Rookery, select wineries, and Monterey Bay Aquarium. Then I had a running list of other things to do that would be good for adults and kids that we could reference as the trip unfolded. This approach kept everything flexible, avoiding insane itineraries that prevent opportunities for spontaneous joy and curiosity.

Skip-generation travel is a beautiful reminder that travel isn’t just about the destination or checking things off a list. It’s about time spent together, conversations shared, learning through doing, positive influence, and exploring the wonders of a world we’ll one day leave, hopefully better than we found it. 

By our actions and through our legacy, we create stories worth telling, sharing an appreciation of our planet and humanity that will live long after we are gone.

In upcoming articles, we’ll dive deeper into each destination, providing detailed recommendations for accommodations, dining, and activities that make each stop along California’s coast perfect for families, grandparents, and everyone in between.