Local Sing Along Anagada

Captain and Founder

Scott Dempster | Captain and Founder

Captain Scott holds a USCG 50-ton captains license with several endorsements, including auxiliary sailing. He is a certified American Sailing Association (ASA) instructor, a passionate and accomplished yacht racer, and a not-half-bad surfer and guitar player. He is also the founder of the only ASA certified sailing school based in the U.S. Virgin Islands.

Scott made his first trip to the USVIs in 2005, and quickly recognized it as a place where he could combine 3 of his biggest passions: sailing, teaching and tropical islands. Soon after, ascribing to Mark Twain’s philosophy that you will always regret what you don’t do far more than what you do, he began captaining charters and teaching sailing in the islands. Realizing the need for an ASA certified school there, and drawing upon his stateside successes as a business  owner and entrepreneur, he founded Virgin Island Sailing School in 2010.

Though it took a bit of cajoling, here are some of Scott’s views on life and sailing from our version of the Proust questionnaire:

Who is your hero in real life?

Pete Townsend; he helped me survive my teen years.

What is your proudest accomplishment?

My son, West.

What is your most treasured possession?

Not sure I have one.

What would you most like to say to your 18 year old self?

Plan more, work less.

When did you buy your first boat?

In 1997, two months after my son was born. A Kettenberg 32.

What’s top on your sailing bucket list?

Sailing with sailors who possess the “old” knowledge of the Polynesians.

How do you overcome things that scare you?

By facing the fear.

What’s the best thing someone has ever said to you about your sailing school?

It was a 3-star Army general who later became a circuit court judge. He said it was the most “adventurous fun” he’d had since he spent a week skiing across the alps as a young man.

Where is your happy place in the Virgin Islands?