Family Sailing Story of 2008

In the summer of 2008, my dad, brother, two family friends Doug and Tom, and I embarked on a 60 plus mile sail from Chicago to South Haven, MI. My father owns a sailboat, so these types of excursions are common. On a lazy August evening we departed, leaving the Chicago skyline and fireworks from Radiohead at Lollapalooza behind. Before we knew it, we’d encountered our first problem – a treacherous V-shaped storm quickly emerged from the night sky. We found ourselves in a downpour, so my dad sent everyone downstairs while he braved it out at the helm. After considering turning around and ending the trip – we decided against it, and soon enough the storm passed.

After the storm, everything seemed to be running smoothly – we had great wind pointing us right on course. My dad, my brother, Doug (my dad’s buddy) and I found ourselves engaging in great conversation until we realized that we hadn’t seen Tom in awhile. My brother poked his head into the cabin and called for Tom. No answer. Could Tom have fallen overboard without us noticing? We heavily considered this possibility, then we dispatched my brother downstairs to go look for him. After a couple minutes of searching, he found Tom asleep at the bow of the boat in the only non-visible spot in that room. We had dodged another bullet and were immediately rewarded by a cloudless, 2 AM sky filled with more stars than I’ve ever seen in my life. We were finally far away from the city lights to see a full sky of stars and it did not disappoint – I likely counted more than 200 shooting stars.

The picturesque evening ended after a couple of hours, when a fresh batch of enormous waves arrived. Of course, it was my turn to go downstairs and get some sleep. I headed to the front room, laid down, and attempt to fall asleep amidst the waves. The waves were so huge, I felt like I was being tossed up and down inside the hand of a giant. Somehow I fell asleep, but the results weren’t pretty when I woke up. I felt utterly seasick. I wasn’t sure if I would be able to make it. The sun had risen, so I tossed a poncho on and headed upstairs. I plopped down in the cockpit, and immediately fell asleep. I was angled in a position that blocked the huge splashes from the waves, but Doug, who was at the helm, wasn’t. So while I snoozed my way through the morning, Doug got soaked at the helm.

Finally, we arrived in South Haven, and immediately went out to breakfast. Since we’d been on a boat for twelve plus hours, we all had sea legs. Doug spilled his coffee all over himself while going for a sip, and my brother ended up running out of the café to throw up in a trash can on the street. We enjoyed the rest of the lazy day in South Haven – I proceeded to take a rough nap on the most uncomfortable spot on the boat. Soon enough, the day was over, and made plans to leave the next day. My brother and I chose to sleep in, so my dad, Doug, and Tom would depart early next morning. My brother and I were simultaneously awakened for a seven second interval around 5 AM the next morning. We heard footsteps pounding and my dad repeatedly yelling: “Doug! Doug! Doug!” Next, we heard a crashing noise and an “Aw shit!” from my dad, then we fell back asleep, with giddy, ironic smiles on our face only imagining the disaster that took place above.

I (clearly) love telling this story because it’s a decently adventurous family tale, with plenty of humor sprinkled in. Sailing is a great recreational activity that annually takes place every summer, in our family. A great part about sailing is the hilarious memories that are made on the boat. Our boat will likely (hopefully) be passed down through generations of our family, and stories like these are just as important as the story itself.