On a winding road in the Santa Monica Mountains of Southern California, three men giggled in a rental car. About what, none were sure. The unbelievable view? The nerves of navigating without cellphone service? The thrill of being together again? Words can get in the way of these kinds of moments. The ones where life tickles you with its most tender and terrifying bits at the same time. A snort-sigh-chuckle became our shorthand.
A hairpin turn on a chunky dirt road revealed clouds spilling over the mountainside, pouring into the valley. A triangle of ocean between two distant peaks. A couple of hawks circling. The layers looked photoshopped.
A snort-sigh-laugh from the back seat. Then, the passenger side. I turned up the music.
We were on our way. From LAX, up the PCH, into the mountains just north of Malibu. The Agave House whispering our names the whole way.
Snort-sigh-laugh.
Welcome to the Gentlemen’s Trip.
We stopped at Neptune’s Net for lunch. Paper baskets. Fried fish. Motorcycles roaring. The last time I ate there was a decade ago with a family friend. I saw a motorcycle fly up into the air, spiral downward, and crash onto the pavement after a wheelie gone wrong.
No such luck this time.
After lunch, we began the climb.
You don’t really arrive at the Agave House so much as you earn it. The road narrows. The turns get tighter. At some point you wonder if you’ve made a mistake. And then a steep driveway appears. Agave plants framing it. And there it is.
It’s hard to believe it’s up there. Like, who built this? And how did they get the materials up here? Let alone a luxury bathtub?
It almost feels like a church. Not in design or stature. But something, I don’t know, I’ll call it spiritual (sacred?) hovered around the place. Or maybe the woo-woo of California is contagious.
We walked in. Slowly. Picked rooms without saying much. Each one with its own bathroom. Which, I insist, is a requirement for a Gentlemen’s Trip. The windows were wide, framing the mountains like they were part of the architecture.
We all just stood there for a beat. Taking it in. Then, almost immediately, we left.
Groceries. Sunglasses. iPhone.
The groceries were for the week. The sunglasses were for Kansas City. The iPhone was for me. Shattered mine getting out of an Uber at O’Hare about seven hours earlier. Travel has a way of taking things and giving things back in its own way.
“Travel makes one modest. You see what a tiny place you occupy in the world.”
—Gustave Flaubert
There were three of us. Me, a buddy I recently reconnected with in Chicago, and another who lives in Kansas City. We all went to college together. Stayed in touch in various ways over the years. But we’ve never traveled together. Especially not like this.
I must admit, I never liked traveling with guys in my 20s. The whole bachelor party, spring break scene wasn’t for me. But then something happens in your 30s. People start having kids. Relationships fade as easily as they fired up. Finding time becomes nearly impossible. And a guys trip becomes this lucid fantasy that never makes it past the group text.
But the world changed.
COVID happened.
Remote work happened.
Male loneliness happened.
Things are different now. And I think a guys trip is necessary for sanity. At least for me it is. But I didn’t want a guys trip. I wanted something better.
A Gentlemen’s Trip.
This one was intentional. I had two goals:
- (Re)Connect with some gentlemen.
- See a celebrity. Because why else do you go to LA?
Happy to report, both would be accomplished by the end of it.
That first night, Kansas City grilled while I set up my new iPhone.
We ate outside as the sun started its slow descent, dissolving into layers of cloud and mountain and ocean. The kind of sunset that doesn’t feel real until you’ve been sitting in it for a while.
We opened a bottle of wine. And another.
After dinner, we moved to the fire pit. No one suggested it. We just drifted there.
We talked. About marriage. About life. About kids (Kansas City is a dad, and a really good one at that). About our parents. And about nothing at all. Food. Sports. A jacket one of us had been thinking about buying. The conversation moved the way it does when no one is in a rush to get anywhere.
Every now and then, the conversation would lull. We’d let ourselves be hypnotized by the fire, by this strange vantage point of earth, and one of us would let out a snort-sigh-chuckle.
We woke up the next day and went to work. The commute was opening the doors wide, stepping onto the patio, and opening our laptops.
The Agave House doesn’t really allow for separation between inside and outside. It insists on both. We’d take breaks by hopping into the hot tub, making a sandwich, going for a stroll. At one point, the WiFi gave out. No cell service up there, either. We couldn’t think of the last time we were in a situation like that. And it felt refreshing. A little throwback.
We drove down to a coffee shop and pretended to be locals. You could call it a disruption. But that’s not the kind of gentlemen that were on this trip. Every small inconvenience had a way of turning into something else. A slight detour. A better story. A reason to see something we wouldn’t have otherwise.
It’s why you have to be picky about who you travel with. You need guys who can go with the flow but who also show up to a reservation on time. Relaxed and buttoned-up at the same time. A rare combo these days.
“Never go on trips with anyone you do not love.”
—Hemingway
That night, we stayed in. A private chef named Guy came up from BirdeyeLA. He moved quickly and quietly through the kitchen, like he’d done this exact thing a hundred times before. He probably had. He told us stories about cooking for larger groups there. One time, for a guided mushroom trip. Can’t imagine appetites were at the forefront of that evening.
He made us steak. Salad. Asparagus. Crispy sunchokes scattered across the greens. Which I’d never had before. I’ve been thinking about them more than I should.
It was cloudy that night. Thick, low clouds swallowing us whole. We opened the doors near the dining table and sat down to eat. And it felt like we were dining in the sky. No edge. No horizon line. Just white and gray and the faint suggestion of something beyond it.
This is the part where I’m supposed to justify the expense. A private chef? Was it necessary? Of course not. But this is the Gentlemen’s Trip. And if you have the means, stop asking if it’s “worth it” and start asking if it’s something you’ll all remember forever.
We will. Food memories have a way of sticking.
Tuesday followed the same loose rhythm. Wake up. Coffee. Hot tub. Work. Etcetera.
That night, we went to Nobu. We didn’t even look at the menu, other than to pick out a Russian River Valley Pinot. “The greatest hits,” the server called it. Sashimi. Nigiri. Salmon. Steak. Shrimp. More sushi. A blueberry dessert. Despite the steady parade of plates, it didn’t feel rushed. And it didn’t feel indulgent in the way those meals sometimes do.
When you’re with the right people in the right place, nothing feels indulgent.
We saw a C-list celebrity there. But I couldn’t count it as spotting a real one.
Back at the house, we ate gummies. Poured wine. Set up a chess board on the table outside. Music on, low.
There’s something about a game that doesn’t require a screen. It gives your hands something to do while your mind wanders. Or focuses. Or drifts somewhere in between.
By Wednesday, we had figured out the rhythm. Or maybe the rhythm had figured us out. We stopped tracking time altogether. Just let the day happen. Walks around the property. Sitting in chairs that faced nothing but mountains. Opening and closing doors like we were adjusting the house itself to match our mood.
The Agave House makes you feel like you’re participating in it. Not just staying there. Every window is a frame. But you don’t really look at the view. You exist inside it. There’s something about the place. The air. The quiet. The way it forces you into a slower version of yourself. It lifts something. Clears something out. Makes you think, briefly but convincingly, that you could live differently. And that you actually might. That interacting with nature might be the difference between a good day and a bad one.
Thursday came quicker than it should have. One last look out the window. One last coffee. The drive back down felt shorter.
The flights to Chicago were delayed. Storms back home. I hopped on standby for another flight. When the gate agent called me and Tim Robinson to the desk, I smirked to myself. Can’t be. And then Tim Robinson walked up.
It was chaos at the gate. Hard to tell what was happening. Names being called. People shifting around. At some point, I ended up with the last seat on the flight. And as I walked away, ticket in hand, it took everything in me not to turn back, hand it to him, and say, “I think you should leave.”
I wish you a Gentlemen’s Trip this year. It did me well.
I’ve been sitting here, looking at a blinking cursor, trying to wrap this up with something meaningful. But the truth is, I can’t. No combination of words will transfer to you exactly what I’m feeling.
So I’ll just snort. sigh. laugh.
