I LIVED IN CALIFORNIA for the first twenty years of my adult life. Most of that time was in Orange and Los Angeles Counties. I loved it, particularly the beaches and the ocean. So I go back a few times each year now that I’m a nomad.

The question each time is where to stay. Nearly the entire Southern California coast is private land. The rest is military and state parks. So my options in the past have been to stay with friends, to pay to stay somewhere (hotel or state park), or to streetdock. I have done all three.

This time things didn’t work out with friends. My Number One go-to friends were out of town. My Number Two go-to friend already had guests. The others did not respond to my query. Maybe I’m not that welcome of a visitor after all.

I wanted a sure thing lined up after my slog from the desert, so I bit the financial bullet and booked a hotel room. The state parks in the area were booked solid. I should have made reservations long ago — like maybe in 1986. Or sooner.

Reassurance from a Pro

I have a YouTuber friend, Scott, who streetdocks all the time all up and down the West Coast. Despite so many jurisdictions making it illegal to sleep in vehicles — even in the parking lots of businesses that would otherwise allow it — he says he has never had a problem, no negative encounters with law enforcement.

My streetdocking experience has been mixed. I’ve received The Knock a couple of times — once in Imperial Beach and once near Monterey. On the other hand, I camped for a couple of weeks in San Diego during a gap when a court order put their intolerance of vehicle dwellers on temporary hold. I spent a night in a church parking lot after a friend had recommended it. I overnighted in an apartment-filled neighborhood in Huntington Beach. I spent a few nights a block from the beach in Ventura. All with no problems. But I never rested well. I always anticipated being chased off. The joy of being by the ocean was spoiled by the nightly anxiety.

Reassurance from Other Streetdockers

This past visit, I wanted to stay longer but my budget didn’t like the idea of more hotel bills. So I checked with iOverlander to see what might be available somewhere not too far from the coast. I was surprised.

There was a spot in a neighborhood of multi-million-dollar homes, on a hilltop with views of the Pacific and Catalina Island. This neighborhood emitted a very strong Very Rich People Only vibe.

These are the types of places with threatening signs and severe restrictions. In some, you can’t even park briefly in daylight if your vehicle is taller than six feet. (We’re going to come out and measure your SUV, Ma’am, even if it is a brand new Mercedes G-Wagon.)

But the dozens of reviewers on iOverlander said, yeah, there’s absolutely no problem streetdocking at that location, that no one cares as long as you behave yourself. So I went to check it out. If it didn’t look and feel right I would cut my coastal visit short and head back to the desert.

Too Good to Be True?

I went in the late afternoon, because I wanted time to make it to the desert before dark if I decided not to stay. I was increasingly skeptical as I drove through the ritzy neighborhood, but as I approached the location I saw a couple of Sprinters and a small Class C, plus a sedan that looked like someone’s home. Shrug. Okay then.

There was a trailhead at the end of the street, so I went for a hike after I parked my van. Although the weather had been wet and chilly the previous few days, this day was absolutely perfect. And the hills were beautiful. What a great place to be. Way better than any Walmart parking lot.

Cyclists and people walking dogs came and went. A carload of teen girls in matching little black dresses posed in the sunset for Instagram-worthy photos. Some groundskeepers finished their work in the small park. A minivan found a place at the curb. The evening commute traffic tapered off (where do rich people go during the day?) and things got quiet. But my nerves didn’t.

I was sure each approaching set of headlights would soon be joined by red and blue flashing ones. I was sure any car that slowed down was taking my plate number and making an angry call, not just preparing to make the turn ahead. Yet nothing happened, and fatigue eventually conquered hyper-vigilance.

What Did I Learn?

Since that particular streetdocking spot had turned out so well, I found some other recommended locations in the beach towns of San Diego County. I could sleep my way south then return to the desert via I-8. But after spending a night in Oceanside and a day at the beach in Carlsbad, I had finally reached my limit of traffic and people — the downside of being on the Coast. It was time for me to return to emptier places. For a while.

I learned that iOverlander listings with multiple positive reviews are probably reliable — assuming they’re fairly recent. Things change.

I learned not all rich people are antagonistic toward us folks of humble means and no fixed address. So let’s make sure we don’t give them reasons to change their mind.

I learned Scott might not be the lucky defier of laws and odds I sometimes think he is. With some knowledge and experience it might be possible to streetdock every night.

And I learned I’m not yet to the mental place of Scott. I still worry.