Sailing Story: Hailey Graf

In Montana, it’s not uncommon to hear people discuss how many generations their families have lived in the state. It’s a point of pride to be able to claim you are a 3rd generation Montanan or a 4th generation rancher in Big Sky Country. However, a legacy mentioned rarely, if at all, is one Hailey Graf can boast about— she is a third generation Montana sailor and member of Montana’s North Flathead Yacht Club. 

“My gramps was a sailor, my dad was a sailor and now I am,” she said. “I grew up sailing on a Catalina 25 and I still own that boat.”

She renamed the Catalina 25 ‘Inheritance’ when her parents handed it down to her and now sails it on the beautiful waters of Flathead Lake in Northern Montana. It is the same waters her father and grandfather both called home. 

“It was always just kind of assumed [I would be a sailor],” she said. “I used to do races with my dad every Tuesday when I was growing up.”

While Hailey may have started sailing young, she loves seeing people develop a love for sailing later in life, just like her own mom did. While her mom’s sailing story started by Hailey’s dad dragging her out on the boat, Hailey says it’s now often her mom, not her dad, insisting they go sail. 

“In the last 20 years she has gone from knowing nothing about sailing, getting motion sick and not liking it to bringing out people on her boat on her own,” Hailey explained. “It’s never too late to learn to sail. You can learn the basics of how to operate a sailboat in a surprisingly short amount of time.”

Watching her mom step up to the challenge of sailing may have been one of the motivating factors for Hailey to push herself in the sport too. Hailey began venturing beyond her hometown waters on regattas and also lived in the West Indies for 5 months as a hostess for a charter company. One of her favorite experiences sailing outside of Montana was participating in the J24 Championships in Seattle. 

She raced on an all-women’s team and said, “It was a huge challenge, we were racing against some of the world’s best athletes.” 

“One of the advantages to being a women’s team, is how easy it is to build the chemistry as a crew,” she told King5 News in Seattle. “So, even though we haven’t all known each other for very long, we do have a very close bond and that helps a lot with our communication, recovering from mistakes quickly, setting your egos aside.”

Now, Hailey is sharing her passion for sailing with a whole new group of ladies– in the Bahamas! This past December, Hailey joined Go Sail Bahamas on an all-women’s sailboat cruise around the Abaco Islands. 

“I’m excited to do more of the international sailing and the relaxing cruising as well,” she said. “Island hopping on a big boat in the Caribbean is so much different than lake sailing. The two worlds are so different you can’t even compare them.”

On the trip, Hailey played a much larger role than just as a participant taking in the gorgeous views. She took the opportunity to become an ASA sailing instructor and receive her ASA 114 for sailing catamarans. 

“Catamarans tend to be a bit more comfortable for the social aspect,” she said. “That’s not something you get as much of on a monohull.” 

Now Hailey is a certified ASA instructor, she hopes she can encourage other women to take up the hobby— just like her and her mom did. 

“If there is any woman out there that wants to get into it, all she has to do is start asking questions,” she said. “There is nothing like a ladies wine night out on a sailboat.”

Once Hailey has some trips as an instructor under her belt, we’ll update you on the newest adventures of her sailing journey!