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  • Zen-Len

    • 63ft Horstman Trimaran
    • U.S. Virgin Islands
    • Checked in 4 days ago

Deckhand - Temporary / Seasonal - Room & Board - U.S. Virgin Islands

Seeking big dreamers / hard workers to prepare boat for Trip from US Virgin Islands down-island to Grenadines (and back)

Ahoy! We have a very unique situation.

We have a highly respected charter boat business in the Virgin Islands. You can see all about our boat and business at www.VirginIslandsSailingAdventures.com

Our sailing yacht, Freedom, is a 63' Trimaran with a 33' beam. We were one of only a few boats to survive the two Category-5 hurricanes of 2017 virtually unscathed. She is a very solid bluewater boat.

What we are seeking:

This year we are focused on maintenance & adventure, and we invite interns to join us. Interns typically have little or no experience on sailboats, but dream of life on the water. Interns must have good character, a strong work ethic and a deep desire to learn. Interns will "learn by doing", as we prepare Freedom for this year's bluewater adventure, and then set sail. COVID-19 travel restrictions and port closings complicate things, but we are determined to find adventure when the boat is ready... are you?

This is a NON-paid position. HOWEVER, we do pay for all your living expenses, providing living quarters aboard Freedom, 3 meals each day, and covering all fuel, dockage, and other related expenses of the trip.

We have chores, maintenance, cleaning, repairs, and upgrades that will be performed before, during, and after our bluewater adventure, where you will learn every skill imaginable to operate & maintain a charter boat, as well as HOW to deliver a "Best-Ever" vacation experience for charter guests.

If this sounds like a great adventure, and the fastest way for you to gain the knowledge, skill, & experience to begin living your dreams of life on the water... what are you waiting for?

I am happy to provide specific details to all inquiries. Contact me.
Best regards,
Captain Zen-Len, s/y Freedom

show hide Position


  • Crew positionDeckhand

  • Type of workTemporary / Seasonal

  • Availability Available now for the foreseeable future

  • Salary Room & Board

  • Expenses to/from vesselPaid by crew

  • Expenses onboardPaid by skipper / boat owner

  • Team / SoloI am looking to hire more than one person

  • InterviewPhone interview
    We will arrange a date and time that is convenient for us both

show hide Vessel


  • TypeSailing Yacht

  • ClassificationFractional rig sloop

  • Make/modelHorstman Trimaran

  • Length63 feet

  • Berth7

  • Sailing from U.S. Virgin Islands , St Thomas

  • Sailing to Grenada , Lesser Antilles, as many as possible

  • Language spoke aboardEnglish

  • Boat descriptionFREEDOM is a very big, solid, heavy Trimaran with a 33' beam with 3 sails, 2 generators, 2 deep freezers, 4 refrigerators, central air conditioning, 2 dive compressors, 26' tender, WiFi, Streaming library of over 5,000 movies, 5 guest cabins, 2 crew cabins sleeping a total of 14 with all the comforts of a luxury home.

show hide Skipper


  • NationalityUSA

  • Age69

  • GenderMale

  • Fluent languages English

  • Qualifications MCA Master Near Coastal

  • Sea Miles 10,000+

show hide Feedback



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I was astonished by the poor conditions aboard Freedom. Especially since Len sent his charter marketing video as a preview of his operation. The video seemed a little outdated but having been aboard, I know it to be outright false. The video may have been legit in 2012 but I'm in disbelief the boat has been professionally chartered in years. Len supposedly created his "intern program" to cull crew with the right stuff. The same "program" that he led me to believe would teach me how to run a boat and possibly a charter business. Neither the boat's condition nor business seem operational and Len's are clearly not models to emulate. Covid has not impeded other captains, yet Len insists it has prevented all but repair work... and every other thing Len or I touched was broken in some way. Lucky me was going to get to fix it ALL. I came with years of professional experience in welding, wiring and resin, and was promised I'd learn from an experienced and professional captain skills that are specific to sailing and sailboats. Onboard, Len insisted that repairing his toaster oven and coffee maker would be valuable to my education. Factored into all the incongruences, it's evident my nautical education was quite secondary in his plans and I left after just three days.

3rd Feb 2021

A Golden Opportunity


My time spent on Freedom with Captain Zen-Len has been one of the greatest opportunities of my life and I highly recommend it to everyone out there who want to improve and enjoy their life. Whatever it is you are looking for in life, you can find it aboard Freedom. The ability to learn practical skills, improve all aspects of your life, and grow as a person is not only possible here but it is encouraged, supported, and seemingly inevitable. Practical skills range from engine maintenance, electrical engineering, plumbing, woodworking, varnishing, machining and metalworking, and fiberglass repair as well as tying knots, sailing, scuba diving, running a charter business, and so much more. The work is extremely rewarding and will give you the skills necessary to work in many industries on and off the water and to become a captain yourself if that is your desire. Through dedicated daily lessons, as well as encouragement and reminders throughout the day, your personal growth will be astonishing and you will walk (or sail) away a better person capable of anything. And I almost forgot to mention that you will be waking up every morning in tropical paradise with the ocean as your personal swimming pool, surrounded by beautiful scenery and immensely interesting things all around. You will eat like a king or queen. Your ideas will be heard and your opinions will be respected. You will be given a powerful opportunity to be your best self while enjoying life to its fullest. Captain Zen-Len is one of the greatest individuals I have ever had the privilege of meeting. He is patient, understanding, kind, full of wisdom, and passionately dedicated to helping his crew achieve whatever it is they are most interested in - he also thinks and works like a tireless machine but you will need to see that for yourself to fully believe it! You will be given equal amounts of responsibility and trust which will empower you to achieve great successes. I have never felt more welcomed in any living and working situation in my life and for this I am forever grateful. I cannot wait for the next opportunity to return to Freedom and continue my training and growth with Captain Zen-Len.

31st May 2020

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