Sail Loot Podcast 042: Wiley Sharp, Part 2 – Owning and Operating a Virgin Islands Sailing Charter

By on November 11, 2016

I have now met Wiley Sharp and he’s a great guy. We flew into St. Thomas to start our week long sailing vacation on Saturday and decided to stay overnight before jumping on a Ferry to  Tortola on Sunday morning. We met Wiley, his wife, Laura, and Steve and Chrissy from Knot Anchored for some of the best sushi on the island at Enkai Sushi Bar.

We also met with Stacey and Jesse on S/V Smitty and just met up with Peter and Jody from Where The Coconuts Grow last night. Meeting all of the people that have been cruising, and that I’ve talked to, has been tons of fun. Everybody certainly has a different perpective to share, and tons of knowledge about ways to sustain the boating lifestyle.

Wiley certainly knows the numbers about putting a sailing catamaran into a luxury cruising charter business. In this episode we finally work the numbers backwards and I even asked a few questions about my own personal situation. I promise that I will get you links to the spreadsheets in these show notes very soon. Right now we’re moored at The Caves on Norman Island and I just want to jump in the water to check it out, but I had to get the episode out for you.

Eating Sushi with Wiley, Laura, Steve, Chrissy, Bob, and Paul.

Eating Sushi with Wiley, Laura, Steve, Chrissy, Bob, and Paul.

The Enkai Sushi Crew

The Enkai Sushi Crew

A Few Things You’ll Learn about working the finances of a Sailing Catamaran Charter with Wiley Sharp in this episode:

  • Working backwards with the costs of running a sailing catamaran charter for a week.
  • Broker’s fees
  • Clearing House fees
  • Yacht Management fees
  • Crew Pay
  • Haul Out Fees
  • Maintenance Fees
  • Sailboat Depreciation
  • Can I become owner/operator of my own sailing catamaran charter boat?
  • Does anybody want to be my Chef/Hostes on my luxury sailing catamaran?
  • Captain and Crew Certification Requirements
  • Owning a dog while owning/operating a crewed yacht charter.
  • Marketing the sailboat and a crewed yacht charter.
  • And Much More!

Links and Resources from this episode:

  • Denison Yacht Sales
  • Denison Yacht Sales – Wiley Sharp
  • Blue Waters VI Yacht Management
  • Knot Anchored – blog
  • Knot Anchored – Listing?
  • S/V Pisces
  • S/V Pisces for sale with Denison Yacht Sales
  • Regency Yacht Vacations Clearing House
  • Ryan Bane on S/V Siren Song – What does he do with his dog?
  • Shane on S/V Guiding Light
  • My quick and dirty Excel Spreadsheet for a Charter Business using the numbers Wiley shared during our conversation. Please let me know if this link doesn’t work or if some of the functionality of the spreadsheet doesn’t work. The first tab contains the notes that I made from my conversation with Wiley. The second tab contains the numbers that I put together. I just used a simple boat loan calculator that to figure out what the monthly loan payment would be for a 15 year, 5%, $240,000 loan. I suggest you play with the monthly boat loan costs in cell C3, the weekly income in cell E2, and the weeks chartered number in I2.
  • Wiley’s Pro Forma Excel Spreadsheet for a 2017 Leopard 58, 5 Cabin Catamaran – Yes. The numbers that are in here when you open this excel spreadsheet are for a brand new Leopard 58 with no boat loan. It’s time to play with the numbers and here’s what I suggest…When you originally open the spreadsheet it may ask about updating or editing some links, but I would click the “ignore links” button. I would then suggest starting with the last tab/worksheet, the “CharterRateWorksheet”. Let’s think about what kind of catamaran you think you can afford. For example, I can’t afford a 2017 Leopard 58, but I might be able to afford a 2010 or 2011 Robertson and Caine Leopard 46 for $400,000 with an $80,000 down payment. Oh hey, would you look at that? Knot Anchored is a 2010 Roberson and Caine Leopard 46. Using that link, I can click on the “Rates an Availability” tab and use those numbers fill out the “CharterRateWorksheet”.  As I write this, it seems as if they’re offering some discounts, but lets just say that the Christmas and New Years prices are the “High Rate” that they have listed – that’s $1540 as I’m writing this on 12/10/2016. On the “CharterRateWorksheet” I’m only going to fill out the numbers for 2-6 pax and the Christmas and New Year’s premiums. Then, I’m going to head on over to the main/1st tab called “IncomeandExpenseProforma”. I need to update some numbers here such as the boat length, boat purchase price (let’s just call it $400,000 for now), down payment amount (20%), the improvements to charter number ($50,000 seems a little excessive from what Wiley and I talked about so let’s call it $25,000 instead), number of cabins and heads (4 each), rate range ($12,750 to $15,450), etc, etc. I also don’t think that a full time crew will cost $70,000. I believe that number is there for a brand new 58 ft catamaran. Let’s make it $56,000. Let’s also make the contract crew $2500 instead of $3000. Notice that these numbers are linked to the Expenses table below. You can play with these numbers all you want! Now…let’s scroll down to the Charter Business Plan section on this same “IncomeandExpenseProforma” sheet. We can keep the 2 weeks of premium bookings in there for all 5 years, but obviously this 46 ft catamaran can only be a 6 PAX boat so the rows with 8 PAX weeks booked and 7 PAX weeks booked need to be zero. Now it’s time to play with the numbers and start guessing about how many weeks you’ll have the boat booked for a 6 PAX, 5 PAX, 4 PAX, 3 PAX, and 2 PAX. Notice as you play with all of these number, how the rest of the sheet updates for you! Personally, the first time I went through this, I had 18 charters in the first year because the business was just getting started, and 20 in years 2 through 5. Have fun with this. See what happens when you get 24, or maybe even 30 charters booked for the year. I don’t mess around with the Expenses and Operations Profit table at the bottom too much because all of those numbers are linked to the 2 tables above. However, I do like to mess around with the numbers in the top 2 tables. For example, what if my Full time Crew costs were $0 because I decided to be owner/operator. Obviously, my Operations Profit at the end of every year would increase by the $56,000 that I had entered for the cost of full time crew. What happens if I change the charter booking commissions from 15% to 0% because I have my own marketing skills that are bringing all of my guests to me (as stated in the podcast, this can be a slippery slope, but hey, what do the numbers look like)? Okay, enough explanation! Grab the excel sheet and have fun!
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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. Phil

    November 18, 2016 at 4:09 pm

    I thought this was one of your most interesting episodes yet. You mentioned putting the proforma in the show notes, but I don’t see it. Will you be posting that soon?

    • Teddy


      January 4, 2017 at 5:44 pm

      I’ts been posted on here for a little while now. I hope you found it!


  2. Pingback: Sail Loot Podcast 043: Jason and Kim Ellis putting Mimzy into Charter

  3. Steph

    January 11, 2017 at 3:30 pm

    Great podcast! I wished we had all this info before diving into boat ownership and chartering! We are half cruisers/half charter boat spending our winters in the VI’s and summers in Grenada and the Grenadines.

    Regarding pets on board:
    You should consider chatting with Wayne and Emily Keese on a fellow charter boat called Manna based out of the USVI. They have a dog named George. They market the boat without George, but give people an option to have a dog on board if they want! Brilliant!!! They board George when necessary, otherwise he lives with them when off charter. They have sailed all the way to Grenada with George, so you can chat with them on the ins/outs of clearing in with pets…especially the BVI.

    They are an interesting couple who do lots of philanthropic related projects, including taking the famous Michal Beans ( from pirate show in Leverick Bay) with them to a remote island in Haiti to drop off supplies.

    They are really sweet and salt of the earth kind of people.

    Tell them that Tim and Stephany on s/v Endless Pleasure mentioned them.

    The other option for you is “captain only” charters. But, life is simpler when a cheffie is on board!!

    Have fun on your adventure! It’s a lot of work…but a bad day at sea is better than a good day at the office (mostly)! ;)

    • Teddy


      January 11, 2017 at 10:46 pm

      Thank you! It sounds like I not only need to talk to Wayne and Emily Keese, but also to you!

      It’s interesting. Chrissy leaned over to me at the dinner table at Enkai and said, “You know you can do this if you want to.” She was referring to chartering a boat under any circumstances that I wanted and possibly getting people to join me without enlisting brokers.

      I’ll have to look into the “captain only” charters. I’ve been finding it difficult to convince women in the Atlanta area with successful careers to move onto a sailboat for the foreseeable future! Go figure! I also have this feeling that once I get there (on a boat, on the water), things will fall into place and I’ll be just fine. I’m working on getting there soon.


  4. Amber Charter

    August 8, 2017 at 5:51 am

    very intresting episode! the links you have added are also very helpful

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