Captain Molly Winkelman

Meet Captain Molly Winkelman: ASA Sailing Instructor

Meet ASA Sailing Instructor, Captain Molly Winkelman! Captain Molly joins us with a wealth of knowledge and experience in her 30-year international sailing career. If you’ve been thinking about signing up for an ASA Sailing Course, now is the time to do it!

Captain Molly Winkelman at the helm of a yacht

Captain Molly Winkelman grew up in Milwaukee, WI and first learned how to sail on Lake Michigan when she was a teenager. Molly gained valuable experience racing and sailing and soon realized her passion for a life on the water. Since then, Molly has amassed thousands of hours on the water, having sailed and taught all over the world, forever in search of the perfect wind.

After graduating with a BFA from Art School in Milwaukee, Molly taught racing and sailing on Jboats on the Hudson River and the Atlantic Ocean for the Manhattan Yacht Club. Back in Chicago and on the familiar waters of Lake Michigan, Molly worked and raced boats like her small laser all the way up to 80-foot boats in major races like the Chicago-Mackinac race – the largest freshwater race in the world.

Since then, Molly’s career on the water has allowed her to travel the world. She taught sailing and sailed boats in places like Marathon, Galveston, Lake Tahoe, Newport, New York, San Francisco, Boston, St. Vincent and the Grenadines, much of the eastern Caribbean, Bermuda, Australia, rivers in Europe and the Mediterranean. Molly had the opportunity to move to France where she taught racing and sailing on multihulls and monohulls. She speaks French and especially loves French culture, including their people, food, and art.

Today, Molly calls the Virgin Islands home half the year and considers Tobago Cays, SVG, one of her favorite sailing spots in the world. She has her 100-ton masters license with both sailing and towing endorsements and for the past 30 years, she has helped students become better sailors, regardless of their experience level. In addition to her career in sailing, Molly is a professional photographer and owns a commercial photography business. She loves animals and enjoys swimming, diving, and art. When she’s not on the water, you can often find Molly on the many hiking trails around the islands.

Molly will be working with sailing students of all levels and creating amazing experiences on the water. Browse our courses and class dates here.