The Crew

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Kyle Hahn

Kyle, often called Captain Redbeard by his friends, is the captain and owner. While completing pharmacy school and working as a community pharmacist, he spent three years planning, saving and bringing his goal of live aboard sailing to life.  He learned to sail small racing sailboats at Lake Lotawana, where he grew up.  After a lot of backpacking and various travel, he decided he needed to see the other 75% of the world.  Without any cruising experience, he bought his first live aboard sailboat off of ebay 6 years ago, and taught himself how to sail it while living aboard his boat on a small lake nearby.  He eventually took it to the ocean in the summer of 2010, and fell in love with the idea of taking it further.  From this point on, he researched and planned for a much bigger trip.


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Kassandra Henning

Kassie is part of the original crew of Winnie. Before the trip she had no sailing experience, but was eager for the rare opportunity to see the world by sailboat. She is excited to continue learning more about sailing and the ports of call along the journey. For now, her career as an oncology nurse will remain on hold while the adventure continues.



Dylan Dwyer

Dylan is part of the original crew of Winnie.  He and Kyle grew up together in Lake Lotawana, a small town just outside of Kansas City, MO.  They have hiked, biked, and kayaked together, and know how to play off of each other’s strengths, weaknesses, and dumb ideas.  Dylan has always had an interest in Kyle’s sailing plans, but after spending a summer in Maine working aboard a 125 foot wooden schooner, he didn’t want to stay landlocked any more.  He was a part of Winnie’s travels from February when the boat left Saint Louis to July when we arrived in Bocas del Toro, Panama.



Ansley Sawyer

Ansley was a wonderful addition to Winnie. We met her at Marina Hemmingway, Cuba after the boat she was crewing on ran aground.

Last May she answered a post for crew needed on a 42 foot Benatau sailboat out of Isla Mujeres, Mexico. Due to several circumstances and mistakes, her boat had a rough passage east to Cuba, and was ran hard aground on the reef just outside Marina Hemingway. Ansley, a prepared and tidy sailor, grabbed her one bag of belongings and abandoned ship. The crew of 3 escaped unharmed, but the boat was a complete loss. Not only would it have been very difficult to pull the boat off of the reef, over the next 48 hours, Cubans swam out to the boat, scavenging anything and everything that could be taken off. We heard of the mysterious shipwrecked American girl, who might be looking for a simple way out of Cuba (note that the U.S. still forbids Americans to travel there freely). After meeting Ansley, we had a few days before we planned to depart Cuba. We spent a day in Havana and took an overnight trip to Viñales . Even after her difficult experience, she wasn’t ready for her sailing adventure to be over. We could instantly tell she has a passion for sailing.

She moved aboard Winnie the day before we departed Cuba for Isla Mujeres, her last port. Our passage lasted just over 72 hours and is still maybe one of our best. She is an excellent cook and a trustworthy helmsman. She stayed on Winnie for one month and left us in Belize.





  1. Miss you guys and the ‘ole rig across the street!
    Dennis says you are well but had a little scare.
    Be safe and enjoy!
    It’s a great website, fun to follow!



  2. Hello Dylan, your cousin in Montreal, QC, Can. Your great grandfather Howard (Bus) Sharp was my Mom’s 1st cousin.Your grandmother Sasha was the flower girl in my Mom’s wedding. Anyway we got wind of your trip and will follow your progress. Bon voyage. Let us know if you ever sail close to us. Your cousin, Toni Taylor (Cappelli)



  3. Gents..nice chatting with you Feb. 18 on the Riverwalk in Mobile, Alabama. Have a great trip..will be following your adventures. And you need 3 folding bike..on my way back to western Canada today



  4. Have a great time Kassie!!! As I was reading this blog…I see tat Winnie was made in my hometown, Warren Rhode Island!!! Cool !!



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