Ready to know more about San Diego?


Seaside in Monterey

A road trip guide to wine tasting, allergy-friendly dining, and whale-watching up north
Monterey Bay Aquarium Monterey Road Trip

The Monterey Bay Aquarium is home to 80,000 plants and animals, including Rosa, the world’s oldest known sea otter

I packed too many shoes. Beige wedges, brown platform sandals, black ankle boots, Nike sneakers, Rainbow flip-flops—you’d never know I’d be spending 16 hours out of my 72-hour vacation in a car. But that’s the beauty of a road trip, a whole backseat dedicated to soles.

Skies the limit on the open road and I’m aiming for the stars.

It’s a Thursday night. My friend and I hit the road at 7 p.m., headed to the Malibu Beach Inn. We’ll set off for Monterey tomorrow.

As we drive through LA, the cars push past us like 20-somethings gunning for the stage at a music festival. We’re no longer in SD.

Malibu Beach Inn

Malibu Beach Inn

Courtesy of Malibu Beach Inn

The Malibu Beach Inn sits along the aptly named Billionaire’s Beach with only 47 guestrooms, which seems right considering the exclusivity of this neighborhood. Our suite has a gaslit fireplace and is outfitted with soft blues and taupes. We’re overlooking the ocean; no, that’s not quite right—we can almost touch it. I imagine that on particularly high-tide days, the coastline disappears from below this balcony, the water line just out of reach.

No need for my Sounds of the Ocean playlist, the crashing waves lull us to sleep.

In the morning, we scan the aisles at Whole Foods, wondering if we’ll bump into Miley Cyrus. She remains elusive, so we drive to Blue Bottle for coffee, only to realize it was mere steps away. The laugh wakes us up, just in time for the five-hour drive.

As Prince Harry’s Spare plays over the speakers, I get comfortable in the passenger seat for the first leg on the 101. Winding through vibrant green hills and thick forested mountains, we take every opportunity to film our view, like the true desert dwellers we are. Before long, we trade Harry’s breathy British accent for stand-up comedy radio. Each punchline shortens the trip.

Toward the last of the six-hour journey, we make a left onto Chualar River Road from the 101 leading us through 23 miles of long, winding two-lane streets. (If you’re prone to car sickness, use the suggested alternative routes, they are longer but there are less switchbacks.)

Holman Ranch

Holman Ranch

Courtesy of Holman Ranch

We’re surrounded by a sea of emerald when we arrive at Holman Ranch’s tasting room. Located in Carmel Valley, it sits inside a 1928 house along the kind of quiet small-town main streets you’d see on Gilmore Girls.

“We are the only ones [here] to do 100 percent estate, 100 percent Carmel Valley appellation,” says tasting room lead Giuseppe Cossu. I haven’t wanted to finish a white in years, but I could settle down with Holman’s light, dry, airy 2022 Pinot Gris.

Cossu tells us that the winery is mostly supported by its members, online sales, and tasting room visits—you can’t find their wines in stores. (Though the owners do ship some to their fave restaurants in their hometown of Alabama.) Since they only release wines twice a year, they sell out quickly, so we savor what’s in our glasses.

Carmel Valley Ranch Monterey Roadtrip

Thanks to the property’s sheer number of amenities, one could pass a lifetime at Carmel Valley Ranch

Later, we pass through pastures, towering tunnels formed by trees, and miles of new foliage to check in to Carmel Valley Ranch, about nine minutes outside of town. Situated on 500 acres of land, the ranch feels like a grown-up summer camp.

The property features everything you could ever need: residential homes, a full-service spa, a golf course, hiking trails, three pools, an apiary, farm animals, organic gardens, vineyards, and programming like honey tastings and picnics with Pablo & Paco, the resort’s two Sicilian mini donkeys.

We live here now, we decide. We’ll tell our friends and family later.

I scan the dinner menu at Seventh & Dolores in Carmel-by-the-Sea, dressed in black ankle boots. Everything is labeled for dietary restrictions—a quick scan tells me what will play nice with my own. It’s satisfying to not have to think. We leave with a few pant buttons undone.

“This is retirement environment,” our Lyft driver, a native, says as we head back. He laughs as we inquire about nightlife. The median home price, he claims, is around $2.5M. I don’t bother to verify; I’ve heard enough to keep my lease in San Diego.

Humpback Whale Princess Whale Watching Monterey Roadtrip

A humpback whale breaches as it makes its way back from Central America to feed in the nutrient-rich waters of the bay

Photo Credit: Gina Thomas

In the morning, my sneakers soften the blow of the run through the parking lot we endure to make our 9 a.m. Princess Monterey Whale Watching tour. Humpback whales breach beside us and sea lions emerge in groups, playing alongside them—only a bloody mary could make it more picturesque.

After lunch, we pass by Rose Books & Obscurities, a bookstore owned by husband-and-wife team Ernest and TK Rodriguez specializing in esoteric subjects primarily from the 17th century to early 20th century. “I always think the secret is to go where older people are, because those are chill, quiet places,” says Yasmine on where to find the hidden gems in the area. A shrewd piece of advice.

Before dinner, we make our way through the renowned Monterey Bay Aquarium and get lost among fascinating sea animals and colorful plant life. It’s a strange feeling as we later sit down for dinner at Passionfish—a place known for its James Beard Award–winning seafood and visits from Big Little Lies cast members. Forgive us, fish.

Passionfish Seafood Dish Monterey Roadtrip

Passionfish’s menu features sustainably harvested fare from small farms, farmers markets, and local fisheries

We pack our bags, and Sunday arrives to send us home. It’ll take seven hours, the crisp robot voice reports. Our one escape from the long drive south is the The Place—home to the East of Eden Fudge Factory and the gas station that, people say, was James Dean’s last stop before his fatal crash.

A dry heat smacks us as we walk outside and into the building, which includes a 1950s diner, a fudge shop, rows of wine, nuts of all types, postcards labeled Sassy Boots, and colonial-era mannequins.

“Do you know where I am?” asks a customer.

“Lost Hills,” says the cashier. Sounds right, I think, wondering whether he packed enough shoes.

By Nicolle Monico

Nicolle Monico is an award-winning writer and the managing digital editor for San Diego Magazine with more than 15 years of experience in media including Outside Run, JustLuxe and The San Francisco Chronicle.

Share this post

Contact Us

1230 Columbia Street, Suite 800,

San Diego, CA