Sail Loot Podcast 041: The Money Side of a Virgin Islands Sailing Charter with Wiley Sharp

By on November 4, 2016

I’ve had several people email me and ask about owning and operating a sailboat charter. I found Steve and Chrissy Solonynko via their Knot Anchored blog and realized that they owned and operated a 2010, 46 ft, Robertson & Caine catamaran, Knot Anchoredfor two years before turning the reigns over to Captain Leon Sheepers and Chef/hostes Monika Kudyba in May of 2016.

I emailed Steve and Chrissy to ask if they would be interested in sharing some information about becoming owners and operators of a crewed sailing catamaran charter in the Virgin Islands. Their immediate response was, “I’m putting you in touch with the guy that made it all happen for us – Wiley Sharp.”

Wiley grew up in the Tampa, FL area and has been sailing most of his life. He now wears two hats as a catamaran broker heading up the BVI area for Denison Yacht Sales and a founding partner of Blue Waters VI Yacht Management with his wife. As you’ll hear, Wiley has a wealth of knowledge about setting up and operating a sailing catamaran for charter.

Wiley and I had a few different conversations, and as I write this I have two Sail Loot Podcast episodes worth of content. I’m leaving for the Virgin Islands on Saturday, November 5th, 2016 and I plan on trying to buy Wiley a beer. I’ll probably ask him more questions. I’ll do my best to record everything. This is being released the day before I head to the Virgin Islands, but if you can think of any questions that you want me to ask Wiley in person, leave a comment below, ask your question there, and I’ll see what I can do!

For now…here is part 1 of my conversations with Wiley Sharp:

A Few Things You’ll Learn about Wiley Sharp and Putting a Sailing Catamaran into Charter as a Sailing Business in this episode:

  • How Wiley met and helped Steve and Chrissy become Knot Anchored.
  • The small world of sailing.
  • How Wiley hailing bridge tenders in the Tampa area got him into sailing.
  • Why Wiley and his wife gravitated to the crewed yacht charter business.
  • Wiley’s size, age, configuration, and amenity recommendations for a crewed catamaran charter boat.
  • The finances of purchasing a catamaran, or any sailboat for that matter.
  • Owning the sailboat under an LLC.
  • Sailboat insurance.
  • Where you should flag and document your sailing vessel.
  • Airport logistics.
  • Provisioning costs for a week long charter.
  • Importing lamb and organic chicken breasts.
  • And Much More!

Links and Resources from this episode:


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About Teddy

I am a 37 year old that just wants to find a way to make a remote income, gather some Sail Loot and cruise the world! I have been sailing for a couple of years now, but mostly on 10 day trips as vacationing crew. I just recently took sailing to the next level by completing my Basic Keelboat, Basic Cruising, and Bareboat Cruising Certifications! I am also Vice President of a Medical Consulting Company, have a Mechanical Engineering degree from Georgia Tech, and have taken several Coding, Computing, and Online Business courses. It's time to share what I have learned!


  1. Matt

    November 10, 2016 at 9:15 am

    awesome episode, really got me thinking!
    would it be possible to share some of your spreadsheet you mention in the discussion. Would be fun to play around with some of my own numbers.

  2. Teddy


    November 10, 2016 at 10:24 pm

    Thanks Matt! Glad You enjoyed it. Yes, I can share some of the spreadsheets, but I may not get them out until next week. I’ll keep you updated.

  3. Chris

    November 17, 2016 at 8:26 pm

    Fantastic episode Teddy been following your podcast for about a year now. If you get a chance I would like to see the spreadsheets too. And I think Wiley was going to send some info over too would like to see that too. Keep up the great work.

  4. Gene Nix

    November 22, 2016 at 1:39 pm

    Love the blog Teddy! Time to add a file / tool share component to your resources tab! ;) Happy to share our spreadsheet that eventually turned “green” telling us it was time to go! Also have several energy management excel tools as well. Ugh… I want to get back out on the water!

    • Teddy


      November 23, 2016 at 4:59 pm

      Totally agree Gene! You want to fire those spreadsheets over to me so that I can get that component of the resources tab going? I hope all is going okay with the house. Tell Kat and Addy that I say hello! You around ATL for Thanksgiving?

  5. mark

    November 24, 2016 at 12:52 am

    Hi teddy,
    Thanks for that very interesting potcast. Where do I find the file with the numbers wiley sent you ?

    Thank you for your very good work. Listening for years from Germany

  6. Daniel

    January 3, 2017 at 6:26 pm

    The problem with all of this is that Wiley is fundamentally a dishonest person. The wonderful people who own Knot Anchored, Steve and Chrissy, had a short and very awful experience with him. You can buy a catamaran and you can make money doing it. But choose your company carefully. You can go with a big, reputable company, like the Moorings/Sunsail, or even Dream Yachts. Or you can go with a small management company on St. thomas or Tortola… there are many of them.

    • Teddy


      January 4, 2017 at 4:22 pm

      So, I have the control to approve or trash comments that go onto this site. I went ahead and approved this one. I try to approve all of them that I don’t think are spam. This might be spam, or you might be trolling. Who knows, below is my response…

      Have you met Wiley? Do you actually know Steve and Chrissy? Unless something has happened since November that I am unaware of, I actually went out to dinner with Steve, Chrissy, Wiley, and Laura just 2 months ago. I had a great time with all of them. In no way was I led to believe that Steve and Chrissy had a “short and very awful experience” with Wiley. In fact, Wiley and Laura were putting them up in their home while they were in St. Thomas. We all went out and grabbed a few more drinks after dinner. It was a good time.

      Do you understand the difference in a crewed charter yacht and a bareboat charter yacht? The Moorings/Sunsail mostly specialize in bareboat charters. Sure, if you so desire, you can ask for (and pay more) for a captain and a chef to be on board with you when you charter a boat from The Moorings/Sunsail, but you certainly don’t have to as long as you have the sailing experience necessary to captain the sailboat. I know this because that’s what I was doing when I met up for dinner with Wiley, Laura, Steve, and Chrissy. I took a week off and booked a bareboat charter through The Moorings in the BVI. I was the captain, and we didn’t pay extra for a chef/crew. We had a blast, but purchasing a boat through The Moorings is much different than purchasing your own boat and running your own business with your own luxury sailing catamaran.

      I do, however, agree with you about doing your research and choosing the your company carefully. The owners themselves have to figure out what path is right for them.


  7. Pingback: Sail Loot Podcast 045: Shooting The Breeze about our Sailing Money with Jeffrey Wettig - Sail Loot

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