We are on the train. Specifically the LIRR.
"You have a type," Philippa says.
"I do not have a type, none of these guys look alike!"
Philippa pulls up a picture of an Edwardian man in a morning coat with a flower in his lapel button. "This is your type."
"What's your type?" I ask. I can't stop laughing.
"Byronic hipsters who are also assholes."
Our train rolls into East Hampton, and the majority of the passengers rise and exit. A girl in all-white is standing in front of us.
"Everyone wears all-white in The Hamptons," Philippa says.
"Why?" I ask.
"I don't know," she raises her eyebrows in the direction of the girl. "everyone just wears all-white."
Around 11 am, Philippa and I alight with a bunch of 30-somethings carrying Everlane weekender's. From the stop we could see our hotel on the top of a hill: The Montauk Manor. Kennedy, our hostess and the organizer of the trip, walks us through the Tudor style entry way through the grounds, where there is a spectacular cliff overlooking the Montauk Pond. She couldn't have picked a more perfect place to stay. I am in disbelief that such a perfect turnkey vacation has fallen into my hands.
"I don't deserve to have this much fun," I find myself whispering to Philippa many times over.
By noon, I was twisting a can of Montauk Summer Ale into the sand at Ditch Plains. I ate a fish sandwich, we caught the end of a surf match and sipped my favorite rose from a solo cup. A man starts digging vertical lines in the sand.
"What do you think he lost?" Kennedy asks.
"That's says more about us than it does him," says Philippa.
Kennedy has made us reservations at The Crowe's Nest. Philippa and I agree to go early to secure a table, it is the most beautiful restaurant I've ever been to. Tables for 8 were arranged under little thatched roofs on a lawn overlooking the pond. String lights hung above an outdoor lounge with firepits and couches. Philippa and I drank watermelon cocktails and sunk into a sofa. By 7 we had our very own thatched-roof table sharing whipped ricotta and rose and scallops. The best evening I'd had in a long time.
I fall into a deep sleep at the hotel.
Philippa, Irene and myself take a car into town for iced coffees and exploration. We meet up with the other girls for brunch at The Surf Lodge, a place so insta-famous I know it before I see it.
There is a woman dining at the adjacent table who says: "This is the second Shaggy song they've played in an hour, so that means it's time to go."
I swim and sun for hours. Philippa sits at the edge of the deep end of the pool and smiles.
"Goodbye," she whispers, before diving in.
More rosé and lobster rolls at Dureya's. Kennedy and I leave there and head directly to our scheduled sunset sail. (The anxiety of knowing that I'll want to write about said sail, creeps up on me.)
"You said you were going to sing with me," says the sea captain, he's playing guitar. I laugh, embarrassed.
"You'll lose all your customers," I say. I look at each of the passengers on the boat. They are sitting in small groups -- an Irish family all blonde and smiling, six Chinese tourists sleeping off the end of a beach day, a young couple on honeymoon popping a bottle of champagne. None of them laughed, the captain did not laugh. The joke doesn't translate.
My friends are the last to board, and I see them dashing up the pier from afar. We all greet each other and sit on the floor of the catamaran. The captain stands to put away his guitar and turns on the motor to start towards the ocean. My second sail of the year.
The captain is able to steer the catamaran by a large pole connected to a rudder at the back of the boat. He and his skipper take turns pulling up sails, catching the wind and eventually pulling us out of an inlet and into the sound. Me and the girls open up a bottle of rosé.
But then something happens.
The conditions are favorable enough that we're able to coast at 8 Knots, and the captain as he wipes his brow, is beside himself. This is a rare ride, normally a sail isn't as smooth.
"If we keep going this fast we'll be in Bermuda in two days," he says.
"Let's keep going," I laugh.
"I'm doing a sail all the way down the coast in October," he says.
"By yourself?" I ask excitedly, having visions of what that pure solitude out on the water would be like.
"No!" he laughs. "That's why I'm telling you."
"All alone for a week?" I say.
"Yes. You just sail during the day—and then sleep—it's nice."
"Do you put down an anchor?"
"No, you'll get a feel for the water and see how she moves through the night. No need for an anchor."
We change directions and head back towards our pier. The captain looks at me and sighs.
"I hope you felt that, I hope you felt what just happened. That was the best sail I've had--" he stops because he's starting to cry. "The best sail I've had in the last 25 years. I mean, it was just..."
In his excitement, he reaches down for his conch and blows it triumphantly. People dining at a waterfront restaurant turn and wave to us. Tears are streaming down his face. I start to cry too, at the realization that he was someone so devoted to his sport and craft that he was willing to do it even if a good day only came every 25 years.
What does it mean then, to truly be passionate? Let's say I hadn't had success writing at all, would I still be doing it? Would I do it for 25 years like this man? And to have a hobby such as his, that depended so much on the sea and the air, and the nature? These are the things I thought as I cried.
"I learned how to sail when I was seven," the captain says, "from a boy who was seven years old. I built this boat myself. I spent so much time." He is still talking through puffy red eyes. He looks out at the other passengers.
"I hope you felt it, I hope you realize what just happened out here," he says. One of the Chinese tourists lifts up a fist in the air.
"I felt it."
Philippa and I are reunited at the hotel and went back out for tacos. Monday was coming and Philippa and I will be the first to depart Montauk on the 1:35 am train.
"I feel like by riding the 1:35 am train we like, 'go hard' or something. Like this train is going to be full of drunks," I laugh to Philippa as we sat on the empty train platform. I suddenly feel very bonded to Philippa and appreciated that she was also an easy traveller, making no complaints. It is announced that the 1:35 am train is delayed by two hours. We decide to go back to the hotel and take the morning train.
We sleep for two hours, hit the train again at 5 am. We arrive at 9:15 am to a sunny, hot Penn Station, thick crowds that move like schools of fish (an undulating carpet of heads and hats and cars). It feels as though I've been in Montauk for weeks and not days. I flop into my desk at the office, there's no time to go home and freshen up. I feel sun kissed. There's sand in my shoes. My hair smells like chlorine. I enjoy this little reminder.