Hey 2+2 bitches:

From what I have been informed, you people are about 1.5 standard deviations outside the normative NVG poster's imbecility. So riddle me this:

I have a Bristol 40 sailboat that was considered well-equipped for its day back in the early-aughts. It's worth about $50-60K. I have a friend in Chicago who wants it.

He is the funniest person on the face of the planet outside of Doug Stanhope and Norm MacDonald. He will have a thriving business of tourists.

Let's estimate an average daily income during the summertime of $500.

The boat is on the East coast.

Money is no object. I am free to do whatever I want, with little opportunity cost because I am a random lunatic.

Do I:

a) hire a captain, and crew the boat all the way up the east coast and into the Great Lakes, all the way to Chicago? My boy will owe me the captain's fees, dockage, etc.

b) put it on a trailer and have it hauled from the mid-atlantic to Chicago, and tell my friend he owes me the transportation costs

c) make like Joe Pesci and light it on fire

What would you do?

a

The transportation costs on having this moved by truck shouldn't be crazy. I don't know the dimensions/weight/etc of this boat, but provided it isn't excessively overdimensional you should be looking at less than 4-5k to have it moved by truck.

A vs B is literally just cost+risk and take the smaller number. I don't know the cost of A so I can't speak to how good/bad it is.

C is very likely the best option because insurance and it's a boat.

I'd be really impressed if you can have this trucked for 5k. A Bristol 40 is 11' wide and probably 13' tall. It'll probably cost 3k+ just to have the mast unstepped/re stepped and get the boat on and off the trailer, plus lay days and a myriad of other fees.

You don't say where on the East coast the boat is so it's impossible to tell you how much it'd cost to have it professionally delivered.

When you say "the average daily income during the summertime is $500" what are you referring to? Gross, net, your cut, or? None of what you've proposed in your op is a good idea in any way. Moving the boat to Chicago for your buddy to charter is a terrible idea.


If you aren't using the boat regularly put it on the market and sell it to the first reasonable offer that comes along.

11' wide, 13' tall does raise the cost of transportation by a solid dollar per mile for a pilot car and 200 bucks a state (roughly) for permits. And yes the kind of people who load and unload boats are expensive and I have no idea how they work or what they charge.

How much does hiring a couple of people to sail the boat all the way to Chicago cost though? Seems like it has to be at least a weeklong trip. Sailing people are cheap? If they are cheap why does it cost 3000 bucks to make the boat ready/unready for trucking?

I generally agree that tying up 70k worth of capex after spending 5-10% of its asset value on transporting it to Chicago so that someone can MAYBE make 500 dollars a day for a couple of months in the summer seems silly.

I know a guy who sails maybe 4x a year, and who spends the rest of the year (and a truckload of cash and time and friction with the wife) maintaining the sailboat.

It's completely insane. He's middle class and doing ok but not super wealthy. For the money he plows into that piece of crap, he could travel and stay in lovely hotels on his off time. For the time he spends, he could have any number of hobbies, a side business, or just have fun. Or hire a crewed far nicer yacht whenever he wants to go out. He's basically bought himself a low end painting/bilging/handyman job with substantial negative pay.

Boats should be sailed regularly or sold.

It's impossible to estimate the cost of moving the boat on it's own bottom since OP didn't say where on the East coast the boat is. $5 per mile generally gets you somewhere in the ball park for a 40'-50' reasonably seaworthy boat. Costs vary widely depending on route, boat, and time of year.

I'm not sure about "sailing people" but boatyards and and marine trades are certainly not cheap.

To put the boat on a trailer all the standing and running rigging has to be taken loose, the sails unbent, and the mast taken down. Unstepping the mast generally requires a crane. Then you have to pay the boatyard to haul your boat out of the water and set it on the trailer using their lift. The truck that hauls the boat will need to have a special cradle or jack stands to support the boat.

When the boat arrives at it's destination you get to pay for all those same services in reverse while adding in paying the rigger to put back together a rig he didn't disassemble and tune the rig once the mast is re-stepped.



The other thing to keep in mind is the value of having a professional crew move the boat vs. trucking it. The added value of trucking the boat is less wear and tear on the boat. The added value of having your boat delivered by a professional crew is having your boat "shaken down". A professional crew will deal with all of the problems that arise and provide you with a good report of the boat, what was repaired and recommended repairs. You'll know the boat is seaworthy.

Having your boat shaken down has a lot of value for most owners. If an owner is preparing to sail the boat themselves they can take comfort in knowing what problems the boat has and how well the boat just performed. If the owner is preparing to sell the boat being able to say "The boat was just sailed x,xxx nm by a professional crew and all reported deficiencies have been addressed" makes the boat easier to sell and provides peace of mind for a buyer.

If your friend is paying for transport, let him decide?

You are already well into the tourist / boating season for Chicago. Fastest method...probably over land...

I would just an equally weighted combination of fastest, safest / securest, & cheapest. Money being an object or not.

Keep the boat...because of the implication.

Even if it was a worthwhile venture, the fact that he didn't just opt to buy a boat nearby where he wants to operate his business is a red flag. Means he's broke / has bad credit, is hoping to take advantage of you in some way, or both.

If your opp has a flush, raise.

You sell it to your friend, "as is, where is. Cash and carry." If he is an avid enough sailor to offer charter boat comedy services, he can handle delivering the boat to Chicago on his own, since (at least according to my limited knowledge of sailing) knowing how to get a boat to go from A) to B) is probably a pretty important part of sailing.

Move the friend to the east coast and charter from there.

I'm starting to have a sneaking suspicion that it's cheaper to sell your boat where it is and buy another similar boat in Chicago than it is to transport your boat to Chicago. Do you know what the spread is even?

Hey sincere posters:

Thanks for your feedback.

This boat has sentimental value to all involved. For some, memories are more valuable than money. I recognize that may be an irrational view to a hedge fund trader, but I asked for input from the smartest people on the internet, and now I have to figure out the best course of action.

Thanks again for your advice.

Never stop being amazed by otherwise intelligent people who dump ungodly sums of money into boats they use a handful of times per year.

You need a license and expensive insurance to run charters. Tons of other expenses. This is a terrible plan.

Yeah every bit of it is terrible. Not to mention, summer is halfway over by the time the boat gets there and set up. So it'll just be sitting in Chicago all winter. May as well sell the thing if you care that little about it.

The opposite is true.

The reason for sending the boat to Chicago is because some of the happiest times we have ever had in our lives happened on this boat. (Dare I say "yacht" given its decline in value? It is still nicer than Ted Knight's scow in Caddyshack.)

From a purely financial standpoint, selling it is the most rational course of action.

As I indicated in a previous post, I understand my decision may seem absurd to an option trader who seeks every penny from every trade. Not all decisions in life need to maximize profit in order to maximize happiness for those involved.

A question such as I posed in the OP would not be made by a penurious individual with a 5-figure option trading bankroll. Both parties in question have 7-figure bankrolls, and are more concerned with sentimentality with regard to the sailing vessel than maximizing a few grand here or there.

By the way:

I am sure some are going to wonder why my boy in Chicago would run Charters if he is flush with more than a million dollars.

He is a complete nutcase. That is all.

You are posting in BFI. Many of the people here trade your net worth daily.

The rational (happiest?) course of action would be to post on a sailing forum, as they will know the ins and outs.
Spoken like someone who inherited their money . Well then it's an easy utility question.

Or broke. Having 7 figures myself (a big LOL at that, by the way), I know plenty of people who rely on the appearance of money to get favors from those that do actually have money.

Make sure you get insured properly. Even then, there are risks you can't cover. Having a "nutcase" borrow your boat to rent it for $500/day on charters for the general public is life and happiness -EV imo.

GL though.

this move sounds like a good idea for an episode of "Shipping Wars"

You should start an LLC or give him the boat to avoid exposing your 7 figures to the whims of a nutcase.

Seriously. Letting your 'nutcase' buddy drive your boat around using it for business is pretty scary. You're both very good targets for lawsuits.

Seems like you've already decided you're willing to overlook the fact that it's a horrible deal financially because you're sentimental about the boat / this guy you seem to have a crush on. Why ask for advice if you've already made up your mind? I mean aside from letting us know you've got da 7 figs.