Sail Training | Cayman to Key West

Sail Training | Cayman to Key West
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Apr 5 – Apr 11, 2014

Depart: Grand Cayman, Cayman Islands

Arrive: Key West, FL, USA
Length: 7 days
Focus:Coastal and Offshore Sailing, IYT Certificate


[tab title=”Overview”]

For years, Caymanian fisherman and traders would sail the Caribbean with cargo for trade, racing their fast and nimble craft to markets further north.   Sea Dragon will re-trace their path, sailing from the turtle rich waters of Grand Cayman to the bustling life of Key West.  You will feel the warm salt spray in the night air as you beat against the trades in the Gulf Stream, just as generations of sailors have done before.

Guest crew will learn all they need to know to sail Sea Dragon well – seamanship, sail handling, and navigation.  In addition, interested guest crew can take the IYT Introduction to Boating/International Crew certification on board. Participants in this trip will experience the thrill of offshore sailing in the tropics aboard a fast ocean racer while learning to handle her proficiently.


[tab title=”Team”]

Eric Loss – Skipper

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A native of California, Eric has been on the water since an early age. He has sailed more than 55,000 offshore miles, and has sailed everything from windsurfers to 115′ schooners, and recently he completed a single-handed circumnavigation by way of the great capes. He enjoys teaching all aspects of sailing, from boat handling and dinghy racing to navigation and seamanship. He is always eager to share his knowledge of celestial navigation. Eric has been involved in sail training for most of his life, and is an US Sailing instructor. He holds an IYT Master of Yachts Ocean with commercial endorsement and a USCG 100 ton master’s license. Eric is also an experienced diver and PADI Divemaster.

Shanley Mcentee – First Mate

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Shanley was born and raised in San Diego, CA and graduated with a BA in Environmental Policy and a minor in Environmental Science from Western Washington University. Having grown up by the sea, she holds a deep passion for Mother Ocean and our ever-growing need for protection and awareness of the problems our environment is facing. She enjoys anything having to do with the sea, from surfing to scuba diving to sailing, and loves offshore passages. She is PADI Rescue Diver certified and holds an IYT Master of Yatchs Offshore with commercial endorsement.


Derrick Lockley

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RYA – Competent Crew
RYA – Day Skipper
Dinghy Sailing
Flotilla sailing in Med.
Weekend sailing around British Isles
Transatlantic crossing (Antigua – Gibraltar, via Azores

Tom Charpentier

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Background & Expertise

I grew up sailing on Long Island Sound in Connecticut and continued on as a competitive sailor through high school and college. I also hold a private pilot certificate and currently work in government relations at the Experimental Aircraft Association in Oshkosh, WI. I focus on regulatory policy affecting small aircraft, aeromedical policy, and aviation safety. I continue to sail and currently race scows on Wisconsin’s lakes.

Expedition Goals

Return to the ocean (I miss the salt air!), have fun making this passage, and spend a week thawing out from the winter!


Jonathan S. Towner

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Background & Expertise

I’m a scientist at the US Centers for Disease Control and Prevention whose team is focused on identifying natural reservoir hosts of viral hemorrhagic fever viruses and determining how these viruses are maintained and transmitted in nature. I have over 20 years training as a molecular virologist with a new found interest in bat ecology. I spent the first 30 years of my life living along the coast in California developing a life long love for the ocean and the outdoors.

Expedition Goals

My goals for this expedition are first and foremost to spend quality time with my daughter as she is introduced to the beauty and power of the open ocean. Secondly, I look forward to learning more about sailing, ocean ecology and what we can do to better preserve this vital resource.

Alexandra Abney Towner

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Background & Expertise

Alexandra Towner is a 15 year old high school student at Chamblee Charter High School, where her favorite classes are Biology and Language Arts. She is especially interested in environmental science, having completed a science fair experiment on the comparison of CO2 levels across the Eastern Pacific, using data collected by the Sea Dragon during its transects in 2012. She continued on to the county level and received the NOAA award. This year she recently completed a project on the affects of herbicides on earthworm populations. When not doing homework and research, you can find her on the softball field playing short-stop or third.

Expedition Goals

1) To extend my knowledge of the ocean, and the shifting environmental factors present due to human pollution.
2) To experience first hand sailing in the open ocean.


[tab title=”Itinerary”]

April 5:  Crew will arrive on board Sea Dragon by 2PM.  After moving aboard and getting an introduction to the vessel, they will have dinner on board, and enjoy swimming and snorkelling on the reefs around Cayman.

April 6:  Sea Dragon will depart Grand Cayman in the morning and set sail for Key West.

April 7-10:  Sea Dragon will be underway, rounding the west end of Cuba, and beating up the gulf stream between Cuba and the Keys.

April 11:  Sea Dragon arrives in Key West, arriving in time so that crew may depart the vessel by 5 PM.


[tab title=”Requirements”]

Crew will require a passport from their home country that will allow them to travel to the Cayman Islands and the United States. There may be specific visa requirements for travelers from countries outside of North America. For specific visa information, contact the Cayman Islands Immigration Department or US Customs and Border Protection.  Non US citizens will need a B1/B2 visa in order to enter the United States by sea in Key West.


Contribution Includes:

  • 6 nights accommodation on Sea Dragon
  • All meals, snacks and drinks on board
  • Sailing instruction
  • IYT Certification upon completion of exam
  • Safety equipment and foul weather gear

Contribution does not include:

  • Transportation to and from Key West
  • Transportation to and from the dock
  • Additional nights spent ashore
  • Personal expense while in port


[tab title=”Kit List”]

Please see our tropical kit list