Featured Instructor: Captain Jenni Hellpap

I was first inspired to sail in my early twenties after reading An Embarrassment of Mangoes by author Ann Vanderhoof.  Her tales of cruising life and traveling the world by the water fascinated me.  It wasn’t a tough sell to get my then boyfriend now husband, Ryan, to take some sailing lessons with me.   

I stepped aboard my first-ever sailboat, an Ideal 18, on Lake Michigan at the Milwaukee Yacht Club for a two-day American Sailing Association (ASA) 101 – Basic Keelboat Sailing course.  Our instructor was a 17-year old kid named, Ben Ross. Teaching sailing for him was just a summer job that was paying the bills for his pilot and fire-fighting courses. Funnily enough, he is actually pictured in the ASA textbook, Sailing Made Easy – and yes, I got his autograph! 

Having spent all my Wisconsin summers in and around the lakes either swimming, fishing or power-boating – I was no stranger to the water.  But there was something SO different about sailing. Moving a vessel through the water by harnessing the power of the wind seemed magical, and I wanted more! 

Needless to say, the “sailing bug” had bitten me hard.  I read every book about sailing that I could get my hands on, continued with my ASA certifications and said “yes” to every sailing experience that presented itself.  Also in my quest for sailing knowledge, I’m not afraid to admit that I got hooked on the SV Delos YouTube channel and their Pacific Ocean adventures. A girl’s gotta dream, right?!?

Captain Jenni Hellpap:

All of my classes and students are memorable and special to me.  Truly, no two are the same just like waves, snowflakes and children – ha!  I never know who’s going to walk down the dock. That’s one of the best parts of being an instructor.  Young Ben Ross never knew how he was going to change the path of my life forever, and I’m excited for each of my student’s future sailing adventures.  Every student is an individual on their own journey. I have no preconceptions or judgments. I just meet them where they are and help them achieve their next level on the way to their sailing dreams.  It’s a very personal experience and quite hard to describe the relationship that gets built between a teacher and her student – like a parent and her child – there are no favorites! Each class is different, amazing and wonderful for a variety of reasons.  That’s one of the many mentally stimulating challenges that I enjoy so much about this career choice! 

Now, that being said about all of my memorable students and classes, I do have an encyclopedia set worth of funny and memorable stories from said classes and students.  One of my favorites is about “Betty the Broom”. While practicing mooring ball pick-ups, our boat hook was lost overboard with the rubber handle grip still in my student’s hand.  The metal rod filled with water and sank to the bottom before we were able to swing back around and pick it up. No worries! Our deck brush helped us grab the mooring ball pendant on the next go round, and we tried swimming down to retrieve our shiny boat hook resting about 40 feet down below us.  In the salty Caribbean Sea, we were not able to free dive down that deep to retrieve it so we tried hailing down various fishermen and scuba dive boats that were around us in the marine park, but alas, we could not find anyone to help us before we had to take off for the day’s sailing lessons and practice.  The next island up the chain, we tried to purchase a replacement boat hook at three different shops ashore without any luck either. Looking back, I wonder why we spent so much time searching for a boat hook because for the rest of our 7-day live-aboard Cruise and Learn class, our deck brush “Betty the Broom” was faithful and helped us retrieve every mooring ball pendant and every Crew Overboard recovery drill.  What a valuable crew member she turned out to be and an invaluable lesson in resourcefulness! 

Everywhere!  Especially warm places.  I’ve really enjoyed my time teaching and exploring in the southern Caribbean.  Grenada and the Grenadines will always hold a special place in my heart. We’re far from crowds, the trade winds blow consistently all year round and there’s a fun mix of sailing exposure from open-ocean passages to island-hopping to countless postcard-worthy destinations.  

Our 2018 LTD Sailing School alumni flotilla in French Polynesia was absolutely spectacular, and I’d go back to the Pacific in a heartbeat. 

Earning my ASA Instructor certifications in Annapolis, Maryland – the sailing mecca– with Annapolis School of Sailing and racing J/105s in the Chesapeake Bay with J World is also on the top of my favorite places to sail list.  But really, I’ve got a sailing “to go” list a mile long. There aren’t enough lifetimes to see it all! Each place is unique and amazing in its own right, and I really do want to see them ALL!!!

Sweet freedom!  Ha-ha, seriously though, there are so many reasons that it’s impossible for me to encompass in a few words.  I sail because I can, because I have to, because it’s in my being – mind, body and soul… because I’ve sailed once, and I can never look back.  I’ve been forever changed. It’s a challenge, a focus, a passion in which I’ve found nowhere else, in no other activity or place, in all the years of my life.  Some people are blessed to have found their passion or their calling early in life – not me – took me a couple of decades, trials and errors – but boy, am I happy I found it!  The joy I feel while sailing and everything that goes along with it is indescribable and insurmountable – nothing else has ever come close… #imanaddict

Captain Jenni Hellpap:

You don’t have to “grow up sailing” or “be rich” to be a sailor.  Coming from a non-sailing background, that was the perception I had about sailing and sailors until I read Ann’s book.  I had never stepped foot on a sailboat until over two decades in, and I am far from wealthy. I’m the first (and only) person in any of my family who sails.  If you are even remotely interested in sailing but don’t know how to get started, my advice is to take a lesson, volunteer as crew and accept a day sail invitation.  It’s truly incredible the doors that will open and how these opportunities can snowball when you simply say “yes” …if it didn’t happen to me, I almost wouldn’t believe it.  I’m SO glad that negative perception about sailing got smashed to smithereens. The fact that I get to teach people how to sail as my career now is really a dream come true, and I must pinch myself to make sure it’s really happening!

Captain Jenni Hellpap:

To “unplug”.  As cliché as it sounds, it really seems like it’s getting harder and harder to find opportunities to disconnect from technology in today’s fast-paced world.  Sailing is one of those rare activities that forces you to slow down and be present, “in the moment” and in nature. To only be concerned with the here and now, not multitasking, not being bombarded with artificial stimuli but really at peace, patient and at one with the environment around you – the wind, the waves, the sun, the rain and your vessel’s interaction with creation in its purest sense.  It’s such a special feeling, like nothing I’ve ever experienced before, and that is just the sailing part alone. I would be completely remiss if I didn’t mention THE PEOPLE. The amazing, like-minded, caring, adventurous and wonderful sailors from a multitude of diverse backgrounds that make up this culture. It’s genuinely incredible to see the comradery, teamwork and trust that is built among crewmates at sea.  Your life is literally in their hands and theirs are in yours. There is no fluff, no “boloney”, no safety net, no one else to bail you out, it’s just you, that’s as “real” as it gets folks. I find it all so terrifying yet an empowering and authentic experience that’s completely lacking in modern society – so go sailing and get real! Why wouldn’t you?!?