# Master Plan to Cruise and Pay For It



## Pauly Dangerous (Jan 31, 2016)

In trying to construct a plan to cruise full-time and pay for it, I have come up with a long-term plan. Can anyone find flaw in this plan, or offer constructive criticism or advice from those that have tried?

!) take appropriate classes (ASA101-108, USCG 6 pack, divemaster)
2) Gain experience crewing on other boats
3) sell house (about $150k cash out) and buy 40'-50' monohull sailboat
4) cruise for a year exploring the Caribbean and gaining experience, using paying crew to offset costs
5) get captain's license
6) start a charter business


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## denverd0n (Jun 20, 2008)

I would say that expecting "paying crew" to offset your costs is pretty optimistic. Before you have an OUPV license you cannot charge people a fee for sailing with you. You can share expenses, but you have to pay your share, too. If you make beer money you'll be lucky.

I would also say that you might want to spend a lot of time on this forum, and others, reading about people who have tried to start a charter business with their personal sailboat. What you'll find is that it is not easy. What's more, there's the old saying that the best way to ruin a great hobby is to turn it into a business.

Not trying to burst your bubble, you understand, but thousands of people have been down this road before you, and only the tiniest minority of them were successful at it.

Good luck.


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## Don L (Aug 8, 2008)

too little money
too many charter companies

too big a dream that hasn't been researched

I'm normally all for allowing people to just jump in and learn as they go, but you are caught up in a fantasy.


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## xort (Aug 4, 2006)

Ditto

Very hard work, lots of dreamers like you driving up competition and driving down prices. Tough to get good steady clientel.

Better to work as a skipper for one of the bigger charter companies, at least at first.


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## Minnewaska (Feb 21, 2010)

Every kind of competition from big corporate, with literally hundreds of boats to other small operators. They can spread fixed costs over the fleet, your revenue has to soak it all up from one boat. Margins have to be thin by definition.

Further, without redundancy, how would you could maintain reliability. Stuff breaks on boats all the time, I mean all the time. If it breaks just days before a booked charter is going to arrive, you could have to pay through the nose to repair or replace it. If you can at all. What if it breaks while on charter. You have no chase boat, no repair crew. A clients ruined vacation is going to be rough.

Then, you'll need permission to run this business wherever it is you are considering, pay taxes, get commercial insurance, etc. 

If you get your Captain license and experience, I would live on your boat and get a job with one of the charter companies.


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## sharkbait (Jun 3, 2003)

Instead of 40-50' mono you need to start looking at 60' cats.


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## jwing (Jun 20, 2013)

If all the concerns raised previously aren't enough to dissuade you, let's look at the most important aspect of your #6. You need to be able to answer these questions that all potential customers will ask themselves: "Why should I go with Pauly Dangerous instead of any of the other hundreds of his competitors? What makes Pauly special?" 

I can't think of any answer that would convince me to spend my vacation time and money with a stranger on a 40-something-foot sailboat that he bought and outfitted for $150K.


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## Pauly Dangerous (Jan 31, 2016)

I'm starting to think I should stick to sailing on other peoples' boats.
Thanks for the harsh dose of reality, that's what forums are all about.
Safety first!
Pauly D
Listen to my radio program on iheartradio.com this Sunday 12-3 for roots reggae with DJ Pauly Dangerous and tell yourself "I prevented that guy from throwing away his life savings on an old sailboat and a doomed dream"


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## MarkofSeaLife (Nov 7, 2010)

Get a job with sunsail/moorings first. As a skipper u learn a lot.
The. Go work for a charter company like Tradewinds and see how its done sucessfully.

Then make tour decision if you can make money chartering.

Its a pretty specialised business


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## jwing (Jun 20, 2013)

I know somebody who sails other peoples' boats - a LOT. Although his life seems to be fantasy-like, he still dreams of owning his own boat and taking it where and when he wants to go. I understand the dream of owning a cruising boat and I share it. 

Other friends of mine think that owning a boat is folly; they bareboat charter whenever they want a sailing trip, and never have to worry about boat maintenance. I understand that, too.

Right now, I'm combining the two philosophies and living my own: Own small; rent big.

My point is: Take your dream, mix in the reality, figure out what you want to do, then do it. Sounds like Pauly is doing just that, so I congratulate him.


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## Pauly Dangerous (Jan 31, 2016)

Right on MarkofSeaLife and jwing, thanks for the positive information, that is the real-deal.
What I really want is the big question. Then question 2 is how to go about getting it without loosing in the long run.


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## Pauly Dangerous (Jan 31, 2016)

I like the idea of cruising until I get a captain's license, then working for a charter company while living aboard my small singlehander somewhere tropical.
How realistic this idea?


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## Minnewaska (Feb 21, 2010)

Pauly Dangerous said:


> I like the idea of cruising until I get a captain's license, then working for a charter company while living aboard my small singlehander somewhere tropical.
> How realistic this idea?


Now you're talking. If you need to charter your boat to want to buy it at all, that's asking for trouble.


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## Pauly Dangerous (Jan 31, 2016)

OK, so how about this:
Budget 150K
goal: cruise and explore indefinitely
1) finish sailing school, crew on a boat or two
2) buy a small affordable liveaboard blue-water cruiser like a cape dory or alberg 30... for 20-30k
3) cruise and explore the Caribbean for a year or two while amassing miles and various licenses like USCG 6-pack and Divemaster
(I'm guessing 30k/year for this)
4) look for work with a charter company


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## capta (Jun 27, 2011)

Take it from someone who is on charter right now, it is not the stuff of dreams. It is very hard work (made especially difficult today by unforecast winds over 30 knots). 
In the first place, inviting total strangers into your home is difficult, be it ashore or on the water. Then supplying meals, liquor and entertainment for these strangers for 7 to ten days requires a great deal of intuition, patience and attention, especially if you are hoping to actually make a profit from the experience.
A lot of folks think with the internet that guests will just fall all over each other to book your boat, but the reality is that if it is to be a profitable business, you are going to need a broker (20%) if you want to actually do more than a couple of charters a year in the Caribbean. There is a LOT of competition. Remember, many of our guests are NOT sailors, but folks enamored by the dream of 'sailing' in the tropics, but not the reality of 'tipping and pounding' that is crossing a channel in 20+ knots of wind. If only it was all only 'sailing' the lees.
People on vacation want to eat well, and that requires a pretty good cook. Unless you get really lucky and marry the cook, you are going to have to pay the cook, and well.
There is a saying in the charter business, "You are only as good as your last charter." Even if the previous 20 charters gave you glowing reviews, the charter brokers will shy away from you if you get some creep that complains. The brokers aren't idiots and realize that there are some people no one can please, but why take a chance if they have other boats available?
Take the advice of those above and go to work for a bareboat company and then move on to full term charter on a fancy yacht if you are enjoying it, but don't set your sights on becoming a success in this industry until you've put in YEARS learning the trade. 
That said, I've never had a job in an office and I couldn't imagine doing anything else for a living. Good luck.


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## sharkbait (Jun 3, 2003)

Pauly Dangerous said:


> OK, so how about this:
> Budget 150K
> goal: cruise and explore indefinitely
> 1) finish sailing school, crew on a boat or two
> ...


That sounds doable. Life on a 30 footer isn't bad at all. I've been at it for 8 years.
I would only mention that a Catalina 30 would probably be better for you. They are much roomier and quite a bit faster.


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## Bleemus (Oct 13, 2015)

Pauly Dangerous said:


> OK, so how about this:
> 
> Budget 150K
> 
> ...


How about this . . .

Go to Antigua for Charter Week and beg your way on a boat. With no resume' you will have slim pickings but you should be able to find one. Work a whole season in the charter biz. You will learn a lot and you will work HARD. After that you will have a lot of knowledge. You won't need sailing school and you will have a much better idea about how to go forward. You don't learn this **** on forums. Capta has good advice. Listen to it.

Sent from my iPad using Tapatalk


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## A-39 Aletheia (Sep 7, 2015)

jwing said:


> Right now, I'm combining the two philosophies and living my own: Own small; rent big.
> 
> My point is: Take your dream, mix in the reality, figure out what you want to do, then do it. Sounds like Pauly is doing just that, so I congratulate him.


Like he said; good advice.


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## Minnewaska (Feb 21, 2010)

Pauly Dangerous said:


> OK, so how about this:
> Budget 150K
> goal: cruise and explore indefinitely
> 1) finish sailing school, crew on a boat or two
> ...


That seems like a reasonable approach and your kitty should easily get you several years down the road. My query is your "indefinitely" part. Not sure how far off your golden years might be, but unless you die prematurely and unexpectedly, virtually everyone moves back ashore at some point. Having medical insurance and a retirement income are important. You'll hear all sort of feedback that medical care is less expensive outside the US and, for many things, that's true. You still need to pay for it, however. If you pull the short straw on your health and need serious life saving care, you need a plan for it.

If you're 25 years old and want to give the lifestyle a shot, go for it, while you can. If you're 55, you'll need to have a backup plan at some point.

Minor input on the two licenses you referenced, but you'll get this down as you go. I doubt (but I don't know) that the 6pack license would do you any good, other than as deckhand. I think a door knob can get the 6pack. I bet a 25 ton master, with sailing endorsement, is entry level to get a job as a charter skipper. Could be wrong.

To teach scuba, you'll need to become an instructor, which is a level above divemaster. Mostly about teaching theory at that point. Divemasters get paid dirt and are generally just sheep dogs and sherpas.


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## tempest (Feb 12, 2007)

If you want to charter in the carribean I believe you'll need to add STCW training to your to-do list. There are 3 day and 5 day courses. It's been a few years since I looked at the requirements. Capta might be able to elaborate.


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## Pauly Dangerous (Jan 31, 2016)

Excellent advice coming in, I really appreciate it.
I'm 45, a carpenter, artist, musician, single, no kids, with equity in a house. I also have a MS in Biology... I've also been a teacher, bicycle mechanic, environmental consultant, lifeguard...
I have some experience sailing and a lot of experience in outdoor sports and adventure: surfing, skiing, canoeing, camping, SCUBA, free-diving, mountain-biking etc. I like solo sports that get me deep into nature.
I crave adventure, and have been wanting to explore the Caribbean for many years. I live in St. Augustine FL, so it's right next door.
I like the idea of singlehanding a small sailboat .
So, I'm trying to decide how to do it. I could continue being a carpenter here, buy a pocket cruiser some day after saving for a few years, and sail it occasionally when I have time.
Or I could sell the house and get right to it. 
If I sell I want to make sure I have a solid plan, which needs an end-game where I am earning a living while I grow old. 
Is there a way to put a Biology degree to work on a sailboat? I bet there is.


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## tempest (Feb 12, 2007)

Well, in order to obtain a CG captain's or Masters License, you'll need to document time aboard vessels. ( lot's of it) 

With a Biology degree, you might be able to obtain work on a Noaa vessel or similar research vessels. Whether that tme would be counted toward a license would need to be checked in to. I suppose it would depend on how much involvement you'd have in the ship's operation. The USA jobs website would be a place to look to see what's out there.


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## Pauly Dangerous (Jan 31, 2016)

Does time on your own boat count?


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## sharkbait (Jun 3, 2003)

You don't need classes or certificates to sail or live aboard anyone who tells you different is just trying to sell you something, or justify their meager existence . Buy a cheap boat and try it out. It's just sailing, not rocket science. The life doesn't agree with everyone, this is why you should start small.


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## guitarguy56 (Oct 10, 2012)

Pauly Dangerous said:


> Excellent advice coming in, I really appreciate it.
> I'm 45, a carpenter, artist, musician, single, no kids, with equity in a house. I also have a MS in Biology...
> Is there a way to put a Biology degree to work on a sailboat? I bet there is.


Paul... most people I know in the marine sciences have not had good results in working the marine field and all of them have MS or PHD's in marine biology or similar... One of them turned to mechanical engineering as a means to put food on the table and a house for his family. After many years trying to make it in the field he is now a professor of marine sciences at Miami Dade College.

My son has two bachelors degrees, one in Micro Biology and another in Bio-Organic Chemistry and he has tried to get anything related to marine biology type work or internship out on research vessels but the field is so bogged down with so many with the same degrees trying to get in... he simply lost interest and took the MCAT and now is med school which promises a better career for him...

I think you have desire and the spirit to make sailing/boating work and only you know what it takes... We can only provide some our experiences and what we've done to get here and give you a better feel on how you can achieve your goals.

Get a small 20-30 ft boat as cheap (but sea worthy) and spruce it up if need be and sail the ends of the world with it... have fun... you are fixated with too many 'what ifs'... one step at time... get the boat first! _/)


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## tempest (Feb 12, 2007)

Pauly Dangerous said:


> Does time on your own boat count?


Yes, you can document and attest to time on your own vessel.

Any time spent aboard other vessels would be signed off by the master, on a separate sheet.

The form looks like this https://www.uscg.mil/forms/cg/CG_719S.pdf

Good luck with your goals.


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## Smyrna (Feb 7, 2016)

Your plan is perfect. Of course it will have some unexpected obstacles along the way but if you have the passion and drive you will succeed. You have the money which, unfortunately, is often the hardest part about really getting into this life. You have a straightforward plan to take you to where you want to go. It can be done in under five years if you really go for it. People will always recommend and provide reasons why not but if you are responsible and in it for the right reasons it will happen. Lots of opportunities exist in Oceania. Endless cruising grounds with thousands of untouched islands and atolls that many people would play thousands of dollars to have the chance to see and explore. If you do make it to the last step, perhaps you should consider that area.
Good luck.


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## chuck5499 (Aug 31, 2003)

Nice dream -- we have been watching "Down Below" tv show on charter boats -- granted we have just only watched the 1st year and it is dramatic and wanted crew that was a bit over the top but given that it gives a small glimpse into the life. 

We have friends who run a charter cat and she is a gourmet chef and diver and great lady and he is a dive master so you can cert with him and he can teach you to sail -- they have all the toys you want to play with and their personality can handle anything thrown at them -- 

They are South Africans and sailed across the Atlantic, all over the western and eastern Caribbean, all over the oceans east of Africa - ie they are incredibly experienced - they have both taken and passed most of the RYA courses you can take - and they have a great boat -- we have our own boat and sailed with them in the western Caribbean and down the eastern Caribbean and what great fun folks - 

They can do almost all their own boat work -- and they are both good looking -- 

The life you want is not an easy life and incredibly hard work - you have to show at shows and put on a presentation to the brokers who help you find clients and that includes a meal or food prep, knowledge and personality to deal with what ever -- 

as above take the required course on firefighting ect and go from there -- and yes our friends had to take all those course too and they got credentials out the ying yang -- 

I think you sound like you want the lifestyle but to be truthful you don't have the credentials, experience, ect ect to do it -- so get your required certs and go as crew on one of the big yachts and have fun when you can and learn the life of sucking up to a bunch or rich [email protected]#$%^ who think their bit of money makes them superior to God -- then think about investing your own money


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## rckfd (Dec 3, 2015)

Sell the house buy a 40+ footer get a go pro and a hot body 20 something and video her. Then beg on youtube for donations. Sit back and collect from all the couch sailing advice giving losers on here...


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## guitarguy56 (Oct 10, 2012)

rckfd said:


> Sell the house buy a 40+ footer get a go pro and a hot body 20 something and video her. Then beg on youtube for donations. Sit back and collect from all the couch sailing advice giving losers on here...


Some people do just that... or so... not sure this is how I'd put photos of my wife/girlfriend but... 'c'est la vie'.


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## sharkbait (Jun 3, 2003)

rckfd said:


> Sell the house buy a 40+ footer get a go pro and a hot body 20 something and video her. Then beg on youtube for donations. Sit back and collect from all the couch sailing advice giving losers on here...


Genius!!!!!!!


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## krisscross (Feb 22, 2013)

Whatever route you ultimately take, do not delay and do not let the dream fade away. It can be done and people became sea bums with much less money and much less smarts. Lots of good advice here but be very, very careful before you spend a lot of money on a boat prior to becoming a really good sailor who has direct experience with the business side of sailing. Best of luck, my friend.


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## Omatako (Sep 14, 2003)

I have a perhaps naive belief that not everybody who wants a week on a sailboat in paradise is expecting The Ritz. I reckon there are folks who would be OK to pay relatively small amounts of money in charter terms/relatively large sums in cruiser terms, to spend time on a well-found, comfy, safe vessel sailing, for example, around Fiji to islands/anchorages that are way off the well-beaten tourist track and who don't expect to be treated as if they were Brad Pitt.

The problem is that the authorities in Fiji almost certainly think it's a bad idea and have space in their jails to prove it.

If this were easy, I have at least five sets of friends with boats like mine who would give up their jobs today.

Still, it seems like a nice way to fund my dream . . . . .


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## Rob Patterson (Oct 22, 2015)

rckfd said:


> Sell the house buy a 40+ footer get a go pro and a hot body 20 something and video her. Then beg on youtube for donations. Sit back and collect from all the couch sailing advice giving losers on here...


That will work for at least a little money and maybe someone cold make a sensation and really cash in.

I was planning to spend my savings. I will try to think of ways to raise cash if it doesn't cut into the diving & etc. too much.


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