Sunset Sailing

By Anna Kate Baxter

I’m sure I looked insane, but I didn’t care. I had five minutes to board Latitude Adjustment and every catamaran in 31st Street Harbor looked identical. White boats with white sails, lined up, ready to be taken out to Lake Michigan. My backpack slapped me on the back as I raced down the pier, frantically searching for anything with the “3rd Coast Cruising” logo.


I checked my phone. 5:57pm. 4% battery. 




I stopped to catch my breath and to decide what to do. I had no way of knowing where Stingray II was, and no time to run full speed in the wrong direction. I was going to miss the sail and lose an $80 Groupon. On my birthday.


“You’ll trip running like that,” said a deep voice off to my right. Two older men standing off to the side of what I assumed was one of their boats. They both wore polite smiles and clothes that looked very expensive. Friendly enough. I usually don’t like talking to strange men, especially alone, but I was desperate. They knew this place, not me.


“Could you tell me where Latitude Adjustment is docked?” I asked breathlessly.


“Never heard of it,” the taller man said. Of course.


“Do you know where ‘3rd Coast Cruising’ is?” I asked hopefully. The man’s face lit up.


“You see that yellow flag flying across the way?” I looked to where he pointed and nodded. “The keep all their catamarans over there.” It wasn’t too far. I definitely wasn’t making it on time, but I could find it, and hopefully 6:00pm wasn’t a strict time.


“Okay,” I breathed out. “Thank you!” I called as I took off running once again.


Rounding the corner of pier where the yellow flag hung, I saw a group of people standing in front of a boat that had Latitude Adjustment painted on the side. Huddled in a circle stood a young woman with brown cropped hair and glasses wearing a full wind suit, two men who favored each other, a woman with the longest eyelashes I had ever seen, and a short older man who was quietly listening to all the others in conversation.


“Hi,” I said softly as way of getting their attention. They all hushed and turned toward me, waiting for me to introduce myself. “Is this ‘3rd Coast Cruising’?” I asked.


“Yes, you made it just in time,” said a young man walking up from behind me. He wore a thin pair of glasses and a 3CC cap. He couldn’t have been more than 26. “My name is Billy Bach and I’ll be your captain this evening. Anna, right? I’ve got you down right here!” Relief washed over me, and my heartbeat began to even out.




I was ready to enjoy a nice evening on the water, hopefully stop for a swim, and see Chicago lit up at night from the lake.


“Alright, everybody on!” Billy called. The girl wearing the full wind suit came over to me with a pointed smile that told me she was about to introduce herself.


“Hi, I’m Kat!” she said cheerfully. “What was your name again?”


“Anna,” I replied. We boarded the catamaran and Billy began giving us a safety briefing and warned us there might be strong winds tonight. He was attractive in an Andy Samberg kind of way. I could tell he hadn’t been doing this long, but still knew what he was doing. Not that I would really know if he didn’t. I was putting a lot of faith in Billy.


“Where are you from?” Kat asked. She started pulling on a rope at the front of the boat like she had some sort of rank here.


“I’m from Alabama,” I said, anticipating she had something to say about it. People always do.


“Ohh yeah, that explains the accent. I’ve only ever been as south as North Carolina for college at Duke. One of my professors called me ‘little lady’ and that was it for me. I moved back to Michigan as soon as I graduated. What are you doing in Chicago?” she was tying up the rope now. But Billy wasn’t telling her stop. The other young woman with long eyelashes was pulling up the anchor, while Billy was at the wheel.


“It’s my birthday, and this year I just decided to take a solo trip. I booked the cheapest flight and booked a hostel when I got here.”


“Wow, that’s cool! You came by yourself?” she asked.


“Yeah, since COVID I haven’t been able to travel much, and I had never taken a solo trip before. I like the freedom of traveling alone. It’s nice to randomly book an evening sail and not worry if it’s something the group wants to do, you know?”


“For sure. It sounds like you need more adventurous friends,” Kat replied.


“All right everyone, we’re sailing out!” Billy called. “For my first timers, you’ll be with Val. The rest of you man your positions from last time.” Now I was confused.


“Hey you two, I’ll be teaching you some terms and simple knots since it’s your first class. Everyone else will know what to do so you can assist them.” As we sailed out of the harbor and out to the lake I sat next to the other first-timer. The shorter of the two young men who looked alike.


“Have you ever been sailing before?” I asked.


“Once, with my brother,” he pointed to his brother who was now raising the sail. “He races on Lake Michigan all the time.”


“Is it always like this? Are there not experienced people to sail the boat?” I asked a little concerned.


“Well, this is a sailing class,” he said matter of factly. What.


“A class?”


“3rd Coast Cruising is a sailing club that teaches people how to sail. Everyone moves up in rank once they’ve completed so much training. Billy just became captain! This is his second sail as skipper.”




Val instructed James and I as best she could, but it began pouring rain. The catamaran was swaying side to side in the water, Billy fought the wind pulling on the steering wheel, and Kat fiercely worked the sails with James’ brother. I sat helplessly watching them all fight the slight storm we were sailing through.


Part of me thoroughly enjoyed feeling like I was being thrown into a Pirates of the Caribbean movie. Sailing with strangers through a storm on a Great Lake. An evening I had miscalculated greatly. But this was exactly the reason I was on this trip. To fill my life with crazy adventures after feeling stuck in the past for so long.


After two hours of sailing, Billy gave the wheel to the older man, Ontario. As we sailed back in the Harbor he told me stories of him and his wife. All of their travels and children and how they decided to retire and join the sailing club. Billy dropped the anchor and Val pulled out her cooler of beer, wine, and charcuterie.


“So how old are you today?” Kat asked.


“It’s your birthday?” Ontario asked excitedly. “We must sing.” I laughed and smiled, embarrassed by now having the whole boat’s attention.


“I’m 21 today,” I said.


“Well here, then,” Val said, pouring me a glass of wine into a plastic cup.


“Cheers!” Kat shouted, and rest echoed, clinking cans and cups together.