Dennis Gregory's Sailing Story

Updated: May 23, 2021

“It’s real easy to go sailing on a sunny day, but what do you do when all of a sudden, you get hit with something that you aren’t prepared for, and that’s when people get themselves in trouble from being just sunny day sailors.”

“You’re not very smart if you think you know everything about sailing,” said Dennis Gregory, an instructor with Go Sail Flathead Lake. Dennis has been sailing for 44 years and he learns something new each time he goes sailing. When he’s teaching, he shared that his students “ask questions that I take for granted” and in that way, teaching allows him to continue to hone his technical skills when sailing.

Once upon a time, Dennis was a master chess player, and sailing, for him, felt like playing chess. He had been commandeered to work on someone’s boat in 1977, and that is how he found sailing. He had no interest in sailing because Dennis comes from a power boat background. He loved boats with speed, but with sailing, he said that “cruising the same boat becomes magic.”


When he’s sailing, he wants everything to be generally right. He wants to teach people how to make magic on the water by getting things right on the boat. When I asked him what he meant, he laughed as he shared that “yes, the technical aspects of sailing are the most important but so is having enough beer on board!” “If you don’t have enough beer, you may as well give it up right away,” he said with a smile.


Dennis has experienced every element of weather from his experience as a racer because racers go out to participate in a race in all elements. No matter whether it’s raining or the winds blowing hard, racers will race. “Cruising sailors generally go out when the sun is shining, and when the weather is nice.” He shared that with weather and because of racing he “learned how to protect the boat, protect the crew, and myself”. 99% of the time he sails on Flathead Lake, which is his favorite place to sail, and specifically in Dayton and Big Arm Bay because there is always wind. He said, “if you have a sailboat, you want wind.”


Dennis shared a wild story about the J/24 race on Flathead Lake on Big Arm Bay that he hosted. The winner would be invited to the J/24 Worlds in Rochester, New York. The J/24 Worlds has the top 100 boats in the world competing. All were J/24 sailboats. 17 J/24’s were from Seattle out of a total of 27 boats in total.


I had to Google information about what exactly a J/24 is, and a few facts about them are that they are fast. Very fast, as they can go up to 20 knots. According to my search, Rod Johnstone designed the J/24 in 1976 as an “American trailer-able sailboat,” and “a one-design racer.” Dennis’ boat was built in August of 1977, and he bought #65 of the boats that Rod built. “The J/24 is the world’s most popular keelboat class, with over 5,500 boats built and over 50,000 people actively sailing in more than 150 fleets in 40+ countries.”


Back to Dennis’ story – he took 2nd place in the Regatta, which was a two-day event. The 1st place person opted out of going onto the race in New York. Dennis also opted out, because he said he didn’t want to go to New York in August.


His brother in-law, Jeff Fisher, had bought a J/24, which he named Maniac. After the J/24 race, Dennis went with Jeff and another family member, Richard, on Maniac to take it across Flathead Lake. Dennis shared that both the large and small sails they tried to put up continued to get knocked over, so they had to bring the sails down so the boat would pop back up because the boat was a self-righting boat.


Then, Dennis turned around to look behind them as they sailed, and he saw a fog covering the entirety of the lake that was fast approaching them. He said he “realized that the wind coming towards them was blowing so hard that it was tearing the water off the surface of the lake and it was becoming what looked like a fog.” They later realized that the fog was a microburst. They all held on tight to something on the boat because when the fog hit the boat, everything on the boat just shook, and instantly they were all drenched. He hasn’t seen anything like it since in his 44 years of sailing on Flathead Lake, but he continues to share this story with his students because that day, he expected to go out for a sail to cruise and be in the sunshine, and the day turned frightening. Thankfully, Richard and Dennis had hopped on Jeff’s boat at the last minute because both were experienced sailors.


“It’s real easy to go sailing on a sunny day, but what do you do when all of a sudden, you get hit with something that you aren’t prepared for, and that’s when people get themselves in trouble from being just sunny day sailors.” Many people buy a boat, take their families out sailing, and when something unpredicted happens, it’s scary, and they wind up loading their boat back onto their trailer.


This is a prime reason for seeking out instructors like Dennis, who can show you the ropes when learning to sail. Any person can sail, and any person can learn, but a person has to want to learn. “It’s not as easy as getting the sail upright in the air and sailing around,” Dennis said, because “you then have to learn to sail.” “You just never stop learning,” he said.


When Dennis was starting out, he got his hands on books like Sailing for Dummies before he took his sailboat out on the water to practice. “Not everyone that comes as a student will become a sailor,” he said. “Learning how to sail is more than a two-day experience. It’s a multi-day experience, and a multi-year experience.” Teaching has helped Dennis be with people and share his experience with people who want to learn.


“There’s three things that make a person a better sailor,” Dennis shared. “One, is enthusiasm. If you are enthusiastic about wanting to sail, you definitely need that. You need to go out with someone who is better than you or take a lesson with someone more experienced than you.” He sailed his first sailboat without any support from a more experienced sailor, and he owned his mistake because he developed poor habits and looked silly out on Flathead Lake. He realized his mistake when a more experienced sailor started to support him with learning more. I asked Dennis what the third thing was, and he laughed very hard, as he forgot the third thing. We both laughed!


And then, he finally remembered. Number three is “spending time on the water.” Drinking beer when the boat is docked isn’t going to teach you how to sail, Dennis said with sarcasm. “Time on the water – you have to be out there, and doing it, and that’s why racing makes a person a better sailor.”

Dennis wasn’t looking for a job but when the opportunity presented itself to work with Go Sail Flathead Lake, he came out of retirement to work with people to teach them a sport and activity he loves. He said he is “fairly demanding” when it comes to winning a race, but if he doesn’t win, he doesn’t “go around moping,” he just drinks another beer and makes plans to go out and do it again.


Dennis has taught his children how to sail, and he sails with his wife, Laurie. Laurie popped in at the end of the interview and shared that all their children are fabulous sailors, and that she has also become a very good sailor! Dennis teaches people “how to get there” with sailing and how to “get the big picture.” If you want to learn and see the big picture of sailing, give Go Sail Flathead Lake a call and ask to schedule a lesson with Dennis.