Meet Sailing Instructor Andy Deen

What does sailing do (or has done) for you?

It’s not an overstatement to say that learning to sail has literally changed my career and my life. A few years back, some friends and family purchased me a three-day sailing lesson as a birthday present, and I was absolutely hooked! After spending numerous days practicing on our local lakes, my wife and I joined a sailing club in Tampa Bay and got more experience on bigger and bigger boats. After the pandemic, I decided to pivot away from my career as a high school Band Director and decided to teach sailing full-time!

Most memorable sailing experience?

Wow! It’s so hard to pick, but one of my top memories was the first time we sailed from Tortola to Anegada (in the British Virgin Islands). This is a technical, open-water sail that some charter sailors choose to forego. The hardest part was convincing my crew (read: “Friends and Family”) that the attempt would pay off. And we’re so glad we took the leap of faith!

What are a couple of your favorite sailing spots?

I know it sounds cliche, but the Virgin Islands are an absolute “Playground for Sailors.” It’s no exaggeration that you will meet sailors who have chartered in the Virgin Islands 5, 10, 15 or more times! Each time you visit, you can balance old destinations and new adventures!

What’s your favorite part about teaching sailors?

I think my favorite part about teaching sailing for a living is the perpetual goal to “teach myself out of a job.” Just recently, I received a video from former students who did their first bareboat charter in Antigua. I love it when my graduates stay in touch and continue to update me as they charter, purchase a boat, etc.

What advice would you give a new student about sailing?  An experienced sailor?

My best advice for new sailors is to allow yourself the grace to fail early and often. Most of the new sailors I interact with are high-achieving, goal-driven individuals who are often leaders in their chosen career fields. These same people are occasionally embarrassed when they make a mistake, as they are not used to such setbacks during their 9-5 job. Whenever I observe this dynamic, I gently remind the student that my job is to provide a safe learning environment that also allows wiggle room for exercises and evolutions to not go perfectly each time.

Now for my experienced sailors- my best advice is to remember that iron sharpens iron! Most sailors I hang with are quick to teach, offer advice, or provide an alternative perspective. While I find that some sailors can be overly competitive, I prefer to hang with the sailors who maintain a collaborative bent.

What is a random fact about yourself?

Unlike many of my instructor brothers and sisters, I did NOT grow up sailing. I am a relative latecomer to the game but am here to say that passion and a desire to learn can go a long way!

What’s on your sailing ‘bucket list’?

Some friends and I did a BVI charter together last summer and decided that Croatia is next on our list! I am adept at Mediterranean-style mooring but look forward to the day when I need to do it.

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