Why I Stay Longer Than I Should

You’re listening to Tide and Light. Episode One. There’s a town on the east side of Maui where the road runs out before the island does. I was supposed to leave on a Thursday. I had the ferry, I had the flight after it, I had the whole careful chain of things lined up the way you do when you’re trying to be a responsible adult who travels. And on Wednesday night I was sitting on the steps of this little rented room, and the light was doing that thing it does right before the sun goes down, where everything turns the color of the inside of a shell. And I just thought, I’m not ready.

Not in a dramatic way. I wasn’t crying into the ocean or having some big revelation. I just wasn’t done. I’d been there four days and I felt like I was finally starting to understand the shape of the place, and the idea of getting on a boat the next morning felt like closing a book in the middle of a sentence. So I stayed three more days. I moved the flight, which cost me something, and I rearranged a couple of things back home, which annoyed a couple of people.

And those three days turned out to be the reason I remember that trip at all. I’m Lily Mae. This is a show about travel, and art, and the slow beauty of living intentionally, which is a phrase I almost didn’t use because it sounds like the back of a candle. But I mean it more plainly than that. I make watercolor paintings, mostly of coastlines and small ordinary things. I travel a lot, mostly to the same handful of places, over and over, which I’ll explain.

And I notice things, and I can’t stop talking about them, and at some point that became this. I wanted the very first thing I ever said on this show to be the truest thing I know about how I travel. So here it is. I stay longer than I should. Almost every time. And I have never once regretted it.

Okay, so, the thing I’ve been thinking about a lot lately is what actually happens to a place in your mind over time. Not the place itself. The version of it you carry. Because when you arrive somewhere new, you don’t really see it. I know that sounds strange, but I think it’s true. On the first day, you’re not seeing the place.

You’re seeing your idea of the place. You’re matching everything in front of you against the pictures you saw before you came. You’re tired, and you’re a little disoriented, and you’re working out the basic logistics of being a body somewhere unfamiliar. Where do I get coffee, where’s the bathroom, is it safe to walk here, what time does the sun go down. The first day is mostly your nervous system catching up to your location. And the second day isn’t much better, honestly.

The second day you’re still performing the trip a little. You’re doing the things. You’ve got a list, even if you’d never admit you had a list, and you’re moving through it, checking the experiences off against the ghost of an itinerary. And the photos you take on those first two days, I’ve noticed, are almost always the photos everyone else took. The same angle. The same view.

You came all this way to take the picture that was already on your phone before you left. I’m not saying that to be cruel about it. I’ve done it more times than I can count. I’m saying it because something shifts later, and I want to talk about when. For me, it’s usually around day three. There’s something about the third day where the place stops being a destination and starts being, just, where you are.

You’re not visiting anymore. You’re a little bit living there, even if it’s only for a week. You know which way to turn out of the door. You have a coffee place, not the coffee place from the article, but the one you actually like, the one where the woman behind the counter has started to recognize you. And once that happens, you stop looking at the place and you start looking with it. I don’t know how to explain it exactly, but it’s the difference between staring at someone’s face and finally having a real conversation with them.

The first one you can do in a second. The second one takes time, and there’s no shortcut, and you cannot rush it no matter how organized you are. This is the part I keep coming back to. The good stuff, the stuff I actually remember, it almost never happens in the part of the trip you planned. It happens after. It happens in the days you almost didn’t take.

Let me tell you about those three extra days in Maui, because they’re a good example of what I mean. If I’d left on the Thursday like I planned, here’s what I would have had. I’d have had the drive out, which is famous, and beautiful, and crowded. I’d have had the waterfall everyone photographs. I’d have had a nice meal and a nice room and a handful of pictures that would have looked, honestly, like everyone else’s pictures of the same place. It would have been a lovely trip.

I would have called it a great trip, and I wouldn’t have been lying. But here’s what actually happened instead, in the days I added. On the first extra morning, I had nothing to do. Nothing. I’d already done the things. So I walked down to this little black sand cove at low tide, which I’d passed before but never stopped at, and I sat down with my paints because I had nowhere to be.

And I was there for maybe two hours. And in that two hours, an older man came down to fish, the way he clearly did every morning, and he didn’t say anything to me at first, and I didn’t say anything to him. And then he noticed I was painting the rocks, and he came over, and he told me that the cove had a name, an old name, and what it meant, and that his grandmother used to gather a particular kind of seaweed there. And he told me which restaurant in the next town over actually cooked the way the families on that part of the island cooked, not the way the menus said for the visitors. None of that was on any list. You cannot search for that.

That conversation happened only because I had an empty morning and a reason to sit still long enough for someone to walk into it. That is what you’re buying when you stay longer. You’re not buying more sights. You’re buying the empty hours where the real things have room to happen. There’s a word I keep reaching for, for this, and the closest I can get is the difference between visiting a place and being in it. Visiting is a thing you do to a place.

You arrive, you point yourself at it, you consume it, you leave, and the place is more or less unchanged by the fact that you were there, and so are you. Being somewhere is slower and it goes both ways. The place starts to leave marks on you, small ones. You pick up the rhythm of it without meaning to. You learn that the wind comes up in the afternoon, so you go to the water in the morning. You learn that the market is dead on a Monday and you stop fighting it.

You learn the particular way the light falls in the late afternoon on one specific wall, and you start, without deciding to, planning your day a little bit around that wall. None of that is information you can be given. It’s not in any guide. It only arrives through repetition, through being there on an ordinary Tuesday when nothing is happening, which is exactly the kind of day most of us would never spend on a trip because it feels like a waste. But the ordinary days are where a place actually lives. The extraordinary days are for the brochure.

The ordinary ones are for you. And I think we’ve gotten this exactly backwards, the way most of us travel. We treat the trip like it has a budget of experiences, and we try to spend it as fast as we can before we have to leave. More places, more views, more things done. And then we come home exhausted, with a phone full of pictures, and a strange flat feeling that we can’t quite name. I think the flat feeling is grief, honestly.

It’s the small grief of having been somewhere without ever really arriving. You went, but you didn’t get there. Because getting there, the real getting there, the kind that changes you a little, that happens on a clock you don’t control. It happens on day five, on day nine, on the morning you didn’t plan. And if you’ve already left by then, you just never find out what the place was actually going to give you. I want to be honest about something, though, because I don’t want this to sound like I think I’ve figured it all out.

Staying longer is a privilege, and it’s not always possible. Sometimes you have the days you have, and that’s it. The flight is the flight, the budget is the budget, the people back home need you back. I’m not telling you to abandon your life and live on a beach. That’s its own kind of fantasy, and it’s not even a very honest one. And I should say, staying longer is not always some beautiful thing.

I want to be careful not to make it sound like the extra days are always golden. Sometimes you stay an extra day and it rains the whole time and you sit inside feeling like an idiot for moving your flight. Sometimes the magic doesn’t come. I’ve had empty mornings that stayed empty, where nobody walked into them and nothing happened and I just felt a little lonely and far from home. That’s part of it too. Travel is also the bad ferry, and the food that disagrees with you, and the afternoon where you’ve run out of things to feel and you’d give anything to be on your own couch.

Slow travel doesn’t protect you from any of that. If anything it gives the boredom and the homesickness more room to find you. But I’ve come to think that’s part of the deal, not a flaw in it. The hours that turn into something and the hours that just sit there, flat and gray, come from the same place. You can’t have the one without risking the other. The empty morning that gave me the old man and the seaweed is the same kind of morning, exactly the same kind, as a dozen empty mornings that gave me nothing at all.

I just don’t remember those ones. So I’m not promising you a reward for staying. I’m just telling you that everything I treasure came from leaving room for it, and that the room doesn’t come with a guarantee. What I’m actually saying is smaller than that, and I think more useful. If you only have a week, go to one place, not four. If you only have a long weekend, pick the closer thing and stay the whole time, instead of driving three hours each way to see something you’ll only have ninety minutes with.

The instinct to see more, I think, is the thing to be suspicious of. Because more places almost always means less of each one. And less of each one means you stay forever on day one, the shallow day, the day where you’re still just matching the place to the postcard. Depth is a choice you make at the cost of breadth. You can’t have both. I made my peace with that a long time ago, and it’s why I go back to the same places again and again instead of collecting new ones.

I would rather go to Hawaii fifteen times than go to fifteen countries once. Some people hear that and think it sounds small, or unadventurous, like I’m afraid of the world. It isn’t that. It’s that I think the world reveals itself to people who come back. The first time you go somewhere, you get the surface, and the surface is real, and it’s beautiful, but it’s the surface. The fourth time, the place starts to let you in.

You start to see the seasons of it, the way it’s different in the rain, the way the same beach has a completely different character in February than it does in August. You start to recognize people, and they start to recognize you, and a recognized face is the beginning of every good thing that’s ever happened to me while traveling. That isn’t something you can buy or book or optimize. It’s just time. So if there’s something I’d quietly invite you to try, it isn’t a tip exactly. It’s more of a question to carry with you the next time you’re somewhere and you feel the pull to move on, to get to the next thing, to make sure you’re not wasting the trip.

The question is just, what would I find if I stayed. Not, what am I missing somewhere else. What’s still here, that I haven’t slowed down enough to see yet. And then, if you possibly can, give the place one more day than feels reasonable. Build in the empty morning on purpose. Leave a hole in the itinerary big enough for a stranger to walk into.

Go back to the same cove twice, and watch how different it is the second time, when you already know its shape. I’ve started thinking of those extra hours as the actual trip, and everything else as the part you do to earn them. The sights are the cover charge. The empty days are the show. There’s an old man on a black sand beach in Maui who told me the name of a place, and what it meant, and where his grandmother gathered seaweed. I think about him a lot.

I never would have met him on a Thursday. I almost left on a Thursday. Next time, I want to talk about Hawaii specifically, because it’s the place I keep returning to, and it is so much more, and so much more complicated, than the version most of us are sold. There’s the Hawaii from the brochure, and there’s the actual place, with its own history and its own people and its own quiet grief about how it’s been loved, and they are not the same thing, and I have a lot of feelings about the difference. So that’s where we’re going. But for now, I just wanted to start with the one thing I’m most sure of.

I’ve never once regretted staying longer. I’ve regretted leaving early more times than I can count. I’m Lily Mae. This was Tide and Light. Stay a little longer than you should. I’ll see you next time.