Empowerment on Water: Female captain breaks boating barriers

By Abby Chatfield

Sun contributor

Whether it is hobby or career they seek, it is difficult for females to enter the sport of boating. Sailing is especially challenging in northern Michigan, where weather only permits a six-month season in contrast to warmer climates that offer more time during the year to practice.

“It takes a really brave person to go into hibernation and come out boating again after a long break,” said Captain Stephanie Watkins, a Leelanau County resident and possibly Traverse City’s first female sailing captain.

Captain Steph was the only known female captain and sailing instructor in Traverse area from 2014-2018. Since then, just one other woman whom she is aware of has entered work in the field and is employed by Great Lakes Sailing Company.

So how did Captain Steph break into the northern Michigan sailing scene? “I have never been rusty,” she says. “I’ve been sailing consistently since I was 16 years old.”

Her passion for life on the water equates to sailing more than 30,000 nautical miles in the Florida Keys, inland lakes of Oklahoma, US/British Virgin Islands, Puget Sound, Sea of Cortez and the Great Lakes. Captain Steph holds a USCG 100-Ton Master License and all credentials needed to meet the professional requirements set by the American Sailing Association (ASA). She believes, “There are three main characteristics of a good captain: a strong nervous system which makes you unflappable, to be good with people, and a ton of experience.”

Stephanie was born in Wyandotte, Michigan, but moved with her family to Oklahoma in the early 1970s, where they lived along the Oklahoma-Arkansas border for most of her adolescence. When she was 16 years old, an opportunity in Florida arose to sail from Fort Meyers to Key West. This three-day trip planted a seed that grew into a future on water for her.

When Stephanie was 24 years old and working as a hair stylist, one of her clients presented an opportunity for her to sail on Grand Lake o’ the Cherokees in northeastern Oklahoma, a lake popular with sailors due to prevalent winds along its 46,500 surface acres of water. She recalls her first day sailing on Grand Lake with the only instruction provided being to head in a certain direction and, if she capsized, to right the boat by pulling down on the Daggerboard. She capsized more times than she could count but was hooked by day’s end.

She continued to train on the lake and, by that summer’s end, mastered the Laser sailboat. Soon after, she purchased her own sailboat. For 10 years, she pulled it to different lakes in the quad-state area of Oklahoma, Arkansas, Missouri, and Kansas.

Stephanie’s next adventure arose in St. Thomas, where from 1999-2002 she raced Lasers through the St. Thomas Yacht Club and worked as first mate on a sailing charter boat taking people around the British Virgin Islands.

She joined an ashram and became a Kundalini yoga instructor before moving to Key West to eventually work as a sailing instructor. During her decade in Key West, an impactful and fulfilling era of her life, Stephanie taught high school art before committing her full self to the water once again. She ran the Key West Sailing Club’s program for kids, earned her certification to teach adults and instructed for a high-performance racing school called J-World. Summers were all about sailing with the kids, while winters focused on teaching adults on J/24 sailboats.

Curious to experience the northern part of her birth state, Stephanie moved to Traverse City in 2014 to help a friend manage his new food truck. She purchased a van to stay in until she found a place to live, helped at the food truck in the Little Fleet parking lot, and found her way into a position with Traverse Area Community Sailing (TACS) as an instructor for adults. She worked towards her captain’s license while teaching at TACS, earning the license by 2015.

Inspired by her students’ desire for more, Captain Steph contacted Great Lakes Sailing Company (GLSC) to set up lessons on larger vessels. GLSC is an ASA award-winning sailing school and charter business that operates out of Elmwood Township in Leelanau County. They soon hired her, and she began working in the office while continuing to teach for TACS. By the end of the year, she was instructing for GLSC.

By winter of 2019, a burning desire to sail year-round took her to La Paz, located on the Sea of Cortez in Mexico’s Baja California Sur. She spent two winters working for GoBaja, an ASA sailing school. One summer, she returned to Michigan to lead the Boy Scouts on water for its High Adventure Program’s Great Lakes Sailing Adventure, living onboard a 52-foot Alden-designed Ketch with the scouts as she sailed them around the Straits of Mackinac.

A tempting offer in 2021 from the Maritime Heritage Alliance (MHA) lured her back to Leelanau County. She became a captain on the Schooner Madeline, an authentic replica of a 19-century schooner built and owned by MHA, and an instructor for youth in the MHA’s Sail Champion Program, both which she continues to do today.

Through participation in the Sail Champion program, youth work alongside peers, professional crew and volunteer staff to learn how to sail in a format that teaches teamwork, self-awareness and resilience. Captain Steph also coordinates the MHA volunteers to help crew on Champion and takes people sailing, including TACS students for week-long excursions through a partnership she assisted the two organizations in forming.

She was recently asked to write letters of recommendation for four siblings from a family she had previously worked with who wanted to sign up for more training through TACS. “Sharing my experience of those kids’ transformation on Champion was special to me, and I am thrilled that they were all taken into the scholarship program and will be able to get more sailing experience and the growth that comes with that,” she said.

Captain Steph expressed that she formed heartfelt connections with hundreds of kids she taught while watching them come of age through their sailing experiences. “To watch their growth, their minds light up and their hearts come alive with the magic, beauty, science and mystery of sailing right before my very eyes has been one of the best parts of my life. They feel excited, but I see transformation. I am humbled to be a part of their awakening.”

This spring Captain Steph arranged a partnership between MHA and LyfMotiv, a local adventure tour company that hosted outings for YMCA summer camps. MHA provided the boat, Champion, while Captain Steph handled sailing the campers from Northport’s harbor to South Manitou Island.

The YMCA campers explored on land with LyfMotiv guides, while she watched over Champion anchored in the waters just offshore. One night, a storm hit the island and forced her to pull anchor, Champion running ashore. She was able to motor off in the middle of the night. Champion is a 52-foot gaff-rigged cutter with five sails, yet the power of a Lake Michigan storm was nothing to take lightly. Champion was also utilized, with Captain Steph at the helm, to transport the South Fox Island Lighthouse Association between Northport and South Fox Island.

When asked what part of her career she has enjoyed most, besides her work with youth, Captain Steph shared it has been helping women feel empowered on the water. A program she started in Key West called She Sails still exists in Traverse City today. When she first made the move to northern Michigan, Dave Conrad from GLSC agreed to let her use one of his boats to train women to sail after work two nights a week. A sailing and mentoring program for women on the water, She Sails was the first women’s program in the area. Now Irish Boat Shop operates Ladies at the Helm, while TACS continues the She Sails program renamed as Women on the Water.

A focus on doing more with women on water could resurface in Captain Steph’s future. As she keeps her eyes on the approaching horizon of retirement, Steph envisions finding time to sail her 34-foot Irwin Citation, Rosie, named after her grandmother. She wants to sail the North Channel, the Door County area and Georgian Bay.

Those who appreciate spending time in nature might relate to Captain Steph’s shared sentiment regarding her lifelong passion, “Sailing is healing through nature. It gets me off the grid and back to one with Mother Nature.”