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Old 02-09-2014, 01:38   #1
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Selling Home and Law Practice to Livaboard in the USVI

Hello! First time poster here, although I have read hundreds and hundreds of posts. My wife and I have recently discovered a benefit of having children so young... We are empty nesters at age 41. We are ready for an adventure! We have fallen in love with the USVI, in particular St. Thomas & St. John. Each time we visit we spend as much time as we can on the water with day sails, etc.

We are quite seriously contemplating selling our home, selling my law practice, paying off all debts and saving to pay cash for a sailboat to livaboard in the USVI. I estimate we are about 2-3 years out, with a budget of around 40k for the boat.

We will need to moor or anchor out to keep things affordable, so we will be dependent on solar and wind. I consider myself a handyman and mechanic of sorts, and have lots of tools. I welcome the new challenges of a marine environment. We have no illusions that life on board will be a romantic piece of cake, or that "life" in the USVI will be the same as "vacation" in the USVI. I will go to sailing school, and learn all that I can by studying as seriously as I did for two graduate degrees.

Regarding income, we do not have much of a nest egg, and will still be working. My wife owns an internet based business that could transition to a boat rather seamlessly. I will likely start a couple of internet based businesses myself. I may also crew for others to gain experience towards my six pack license. A captain's license would allow us to start our own day sail business with our boat to further supplement income. If we were able to save enough in a given year, we would head South for hurricane season to explore, returning to the USVI after the hurricane season.

I know that if it doesn't work out, we can return to the States where I could start and build another law practice and feed us. However, we have reached a chapter where we would really like to change up the daily grind for a few years or perhaps indefinitely.

My questions for the Forum:

1. What do you think of the above plan? Please be candid

2. Have any of you attempted a daysail business in USVI / BVI? If so, how was your experience?

Thank you in advance for your replies!
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Old 02-09-2014, 02:00   #2
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Re: Selling Home and Law Practice to Livaboard in the USVI

I think you are cutting it too fine with the funds. I doubt a 40k boat would be charterable and I'd guess the fees and insurances required would add up to more than the annual income. It's a good plan but I think you would need to look at investing closer to 200k to receive any sort of liveable income from chartering. Doing courses and becoming certified is a great idea, I'd suggest make a plan with realistic budgets, do as much study as possible while you are working and put a few more $$$ in the kitty over the next couple of years. Try keep the house, rent it out, use it to borrow against.
I guess so e people would say great plan, go now!
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Old 02-09-2014, 04:59   #3
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Re: Selling Home and Law Practice to Livaboard in the USVI

All good in the planning stage. It's amazing how the "priorities" of land based living can derail the best laid plans.

As far as daysailing charters? I think if it worked there would be a ton of folks doing it. Even the bluewater fishing guys eke out a living.

However if your goal is to offset some costs and share the joy of sailing with people you might have fun. I wouldn't rely on it as a sustaining income.

Another way to look at it is like a B&B. Your boat will be your home. Charterers aren't gonna be expecting to see your laundry hanging on the rails. Plus charterers tend to do this with friends. To meet expectations I guess you are gonna need a boat that comfortably accommodates 6 + crew and keeps the evidence of your living well hidden. They are also gonna want catered lunches.

Then there is insurance cover, yada, yada, yada...
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Old 02-09-2014, 05:05   #4
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Re: Selling Home and Law Practice to Livaboard in the USVI

Greetings and welcome aboard the CF, Jake.
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Old 02-09-2014, 06:41   #5
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Re: Selling Home and Law Practice to Livaboard in the USVI

I know of zero people living on a $40k boat doing day trips. I know people that have condos and run boats in that range for day trips. It's a very tough market to get into which I believe is saturated. The people that have been doing it for awhile have solid contacts with the concierges at hotels, B&Bs etc. New comers come and go all the time. For a newbie I can't recommend it as an income stream. You would be better served, no pun intended, to tend bar.

Never bring up a problem without a solution, right?

Buy your $40k boat, live on it but work as an assistant under contract for a law firm. There is frequently a shortage of lawyers here. I can't believe I actually just said that!!!! Hook up with a firm and work when they need help leaving yourself open to sail.

Idea two. Swallow your pride and go work for a day trip boating business as a mate. You will need a minimum of an STCW and the ability to smile and pour drinks. Benefits? You are on the water 5-7 days a week making $150-$300/day depending on who you work with. You will learn the biz while being paid. Downside? Nearly everybody I know that started in the day trip biz doesn't do anything on the water when they aren't working. That too much of a good thing is true for divers I know that went on to work as dive masters too. If you do what you love all the time there is a risk you will burn out.

Ah yes that internet biz dream on the boat... Despite what the local ISPs advertise, stability and speed of non-land based is poor but at least it's expensive! If your businesses aren't affected by being down in occasion or running slow, no problem.

I'm not trying to discourage you from coming down and living your dream. On the contrary, I don't want you to be another that came down and had a really bad experience because that were uninformed.

A good site with lots to read is VImovingcenter dot com.




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Old 02-09-2014, 10:39   #6
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Re: Selling Home and Law Practice to Livaboard in the USVI

I think one OP said it best, find a little side gig in the law bizz while down there, keeps you in it and a nice additional income, besides the service/tourist industry is not all smiles and sunshine.
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Old 02-09-2014, 11:46   #7
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Re: Selling Home and Law Practice to Livaboard in the USVI

Thanks for the input! If I really crank up the hours and intensity at work, I could double the boat budget to 80k. My wife is the free spirit that wants to go now. I am the practical logical one that would prefer to wait a few years, pick up a couple of rental properties, etc. to support the transition with some passive income. The compromise between us is a 2-3 year plan where we would be debt free and pay cash for a boat.
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Old 02-09-2014, 12:00   #8
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Re: Selling Home and Law Practice to Livaboard in the USVI

If you can't write a check for a boat and need to finance, that opens up another can of worms and expenses. A loan will require insurance. Your limited experience will make insurance expensive. It's much harder to get insurance on older boats and in the price range you are looking at, you will be looking at older models. Commercial insurance for chartering an older boat with an inexperienced captain? Think "bend over"!!! Then there will be clauses. What if a named storm comes by. Will you haul the boat? Be out of "the box" during season? I'm trying not to come off as negative but clearly I'm failing.

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Old 02-09-2014, 12:09   #9
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Re: Selling Home and Law Practice to Livaboard in the USVI

Excellent point! I agree that daysail guests would not want see evidence of living aboard. I hope we could find room to tuck it away for a few hours. The daysail business idea is not necessarily part of the dream, just an idea to keep the dream going. With my background in business law and accounting, I am sure I will drive my wife crazy with budgets and spreadsheets before we pull the trigger on that one.
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Old 02-09-2014, 12:12   #10
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Re: Selling Home and Law Practice to Livaboard in the USVI

A degree in plumbing might prove more useful. Non boaters clog boat heads!!!! Your charter guests will put many things in the head that shouldn't be there and you will get to fix it!!!! That will give you a change to spread sheets of paper. Lol


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Old 02-09-2014, 12:31   #11
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Re: Selling Home and Law Practice to Livaboard in the USVI

Haha bend over ...funny.
Yes mate I think spreadsheets and budgets is a great idea to get a handle on things. Not that you can account for everything but at least you can have close to realistic plans and expectations. Lucky for you your wife is a free spirit. I'm sure she will make your life afloat much more fun and interesting. Ask lots of questions on here to help fill in the spreadsheets in the meantime and you may find it's doable sooner rather than later.
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Old 02-09-2014, 12:50   #12
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Re: Selling Home and Law Practice to Livaboard in the USVI

40k not much to spend. But if you are staying in the islands exclusively, you don't need a "blue water" boat. You are probably looking at 30-32 footer realistically. figure a budget for the things you need to add... it can add up fast.
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Old 02-09-2014, 12:54   #13
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Re: Selling Home and Law Practice to Livaboard in the USVI

Thanks for the input Rubikoop! Very valid points. The daysail business idea is just an idea of a means to an end... an idea to supplement and extend our stay. I am up to the challenge of carving out a piece of a saturated market. I am already competing successfully with a million attorneys! The 6 pack license would have to come first, so that will buy plenty of time to evaluate the feasibility of jumping in the daysail business while gaining the requisite experience. The issue you raise of potential burnout is much appreciated. That would be a real bummer indeed.

Regarding internet connection in the USVI, how feasible is it to rely on a wifi antenna and a hotspot from a boat near STT, STJ or Water Island? Instead, do most livaboards get coverage via 3g/4g cell service? Is ATT the way to go there?

My wife's business fortunately keeps her as busy as she wants to be. A good internet connection and access the the USPS are critical however. I have even considered working with her in her business at the risk of us killing each other in a confined space where she is the boss

It is quite an investment in time and money to take the USVI bar, but I could do that as well, or work as a legal assistant/clerk. My specialty is business law, tax law, estate planning & asset protection planning. My sense is that civil matters and maritime law dominate the legal arena down there. I am up to learning new areas of the law, tending bar, crewing for daysails, or whatever it takes really.
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Old 02-09-2014, 13:27   #14
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Re: Selling Home and Law Practice to Livaboard in the USVI

IMHO, I doubt you will find a suitable boat for $40k. Although living aboard can be done on a modest budget, it isn't cheap. I wouldn't head out without a substantial nest egg or steady income.
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Old 02-09-2014, 13:36   #15
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Re: Selling Home and Law Practice to Livaboard in the USVI

Would you recommend waiting until the boat budget is higher? Perhaps 60 - 80k? I was thinking / hoping for a boat in the 34 - 36 foot range. For example, I have been watching a 1998 Hunter 340 that recently sold down there for around 50k. The plan is to save up, move there to temporary housing and take our time to find a deal on a boat, then move aboard.
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