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Discussion Starter · #1 · (Edited)
Hello,

Long story short, I have spent the last 10 years in the U.S. Army and I am getting out September 27th, 2014. Ever since I watched Captain Ron, I have dreamed of sailing in the Caribbean. My plan is to spend from October to April in the Caribbean learning to sail, drinking rum, and generally not doing anything the least bit Army related. I am currently stationed in South Korea and I have a little bit of vacation I am going to use to take some basic sailing lessons in May. In October, I would like to find a good school somewhere, as relatively cheap is possible, in the Caribbean. I would like to take as much training as I am able to, then spend the remaining months practicing.

First, which school would you recommend?

Second, would you suggest I buy a boat, or try to rent one for an extended period?

Third, are there any internship like programs you would suggest? I would not need to be paid so long as I am learning as much possible.

Lastly, what are your general recommendations? What am I not asking, that I should be?

Edit: My experience is limited to about 5 hours of playing around on a lake with a very small sailboat, and a one week chartered sailing trip in Australia. I have the general idea of things, but I am not quite ready to buy my sailboat and go sailing off into the sunset.

Thank you.

Mike
 

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I would definitely go with a captained charter first, and make sure the reality matches your vision of it.

You can learn a lot in a week from a good captain. Not to mention, there are sailing schools that do that, google "learning to sail on a charter sailboat".
 

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I'm sure there are plenty of people who would say it was a bad idea, but I sure ran into a lot of people who were learning as they went on my last cruise. Just don't try to sail across the Atlantic or to Tahiti or anything. :D
 

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Mike,
Your Post 911 GI Bill may pay for some of or all of any training you wish to use it. Before you go on terminal leave talk to a Vet Rep at the VA and see if you can use it for training. I believe you can.

These guys have a good name for themselves
Offshore Sailing School ? The Best Sailing Lessons at America?s #1 Sailing Schools

I wouldn't recommend you buy a boat until you really know what you want. Try to sail on as many different boats as you can. Maybe even get a trailer sailor and go travelling for a while. Saves you some big money.
 

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Discussion Starter · #6 ·
I will definitely check with the VA. The less I spend on training, the longer I can hang out in the Caribbean.

I am very seriously considering taking a one week long course, then buying a boat and figuring it out. That seems quite reckless though. I am a helicopter pilot in the Army, so I have a good understanding of aerodynamics, navigation, weather, etc... I would like to see a few countries down there and eventually end up in Florida. Is it reasonable to assume I could accomplish this?
 

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I learned the parts necessary to sail / cruise a boat other than sailing by owning the boat and fixing it.
No better way than hands on, but it is a slow and error prone method.

Diesel classes, electrical classes, navigation, etc - beat the bushes at your local community colleges. Mine here (in Annapolis area) are far less expensive than the trade schools and IMHO are just as good if you apply yourself.
The goal isn't certification, it's being ABLE to do the work.
As to the sailing part, stay safe, but again the best way is to do it on YOUR boat. Every boat is different in it's wants and needs and those are what matters. Learn the basics anywhere you can, apply them at home.

Since you are talking cruising I'll go out on a limb, learning how to sail a dinghy is meaningless. Crewing on a race boat that's anything but a beer can race mostly for fun is meaningless.
That dinghy will not sail like a cruiser, and being a winch grinder and rail meat teach you nothing but how to fold a sail. Almost no one takes the time to teach you what is going on around you and more importantly why on a 10 man crew until you've been there a season.
On a 2-4 man / person local beer can bob race, plenty of time for lessons and learning.
Now you racers can hate me all you like, I'm firm in my opinions on that.

You didn't say if you are just getting out or retiring or if you have reserve time etc.
Check out the morale and welfare pages, not just Army, but all branches. Retiree's and reservist get all kind of bene's on the water (the USAF has a marina in Tampa Bay for pete's sake). All of it is very much less expensive than commercial.

Having said that, I call dibs on the docks at the USN air base in Key West.
 

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Discussion Starter · #9 ·
I am not disabled, I am not retiring, and I do not have any inactive ready reserve time to serve either. I am completely done with the army. What this means is that I lose the vast majority of any benefits I had for being in. I am pretty sure I will not be able to access any of those military programs. I will definitely check though.

I am a fairly good mechanic. I am a Maintenance Test Pilot, so I have a fair amount of training on complex systems. If I knew half as much about sailing as I do about the AH-64D, I would be circumnavigating the globe. I am confident that I could repair/replace any of the systems/components on a boat.
 

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I second the suggestion for Offshore Sailing School. Take their one week liveaboard cruising course. You'll become a competent fair weather sailor in that week. You could go on to Offshore and Nav course, if you like.

They have a school in Tortola that is a terrific place to train and become more familiar with the Caribbean. However, their Florida school is less expensive and is the same training.

p.s. Thanks for your service.
 

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Yes, thank you for your service.

If I were looking to jump in with both feet, I'd also go with Offshore Sailing School, followed by the purchase of a boat. The exact size, location, etc. would be based on your priorities and plans once you've gone through the class. Although you have some experience, I respectfully suggest that being the chief cook, winch monkey and captain at the same time will be very different than what you experienced.
 

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Seconded. Thank you.

That said, if you want some inspiration, here is a blog written by two very charming young lasses (In my humble opinion, both instantly wifeable) who said screw it, bought a Cal 27, fixed it up, learned through immersion like you want to do, and aside from a few mostly humorous mishaps are no worse for wear. I've read the whole thing and it's definitely a source of inspiration for me.

KATIE & JESSIE | - Aboard Lovely Louise -
 

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Seconded. Thank you.

That said, if you want some inspiration, here is a blog written by two very charming young lasses (In my humble opinion, both instantly wifeable) who said screw it, bought a Cal 27, fixed it up, learned through immersion like you want to do, and aside from a few mostly humorous mishaps are no worse for wear. I've read the whole thing and it's definitely a source of inspiration for me.

KATIE & JESSIE | - Aboard Lovely Louise -
I love their blog. A good example of what I saw when I was cruising. Lots of people who bought a boat, and learned how to sail it as they went along, without disaster ensuing.

As Al Pacino noted in "Heat", "You can killed walking your doggie."

I would guess that nothing that can happen while sailing would be nearly as dangerous as what someone who has been in the US Army in the last ten years has probably gone through. :)

SensibleMike, I have no doubt can pull this off. It's just making sure you want to pull the trigger (so to speak) and do it.
 

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Another teaching comment on full immersion training.

What you learn fast, you will lose fast. Immersion training is very effective, even recommended, but to make it stick, you have to immediately put it in practice. If there is a big gap between your training and initial use, you'll lose most of it.

Therefore, whether you buy or charter, you're going to want to be in a position to get right out on the water and set that training in permanently. Once you begin to put it in practice, it will be like you learned it over time.
 

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Take a few lessons and then buy a fairly cheap boat that is large enough to live on that is already in Caribbean and "just do it".

Sailing isn't really hard, but sailing well takes time and practice just like anything.
 

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Making the boat go is the first couple of days of a liveaboard course. My wife took it. The rest is spent learning boat systems, anchoring, snubber lines, reefing, man overboard drills, propane leaks, etc. All the stuff you also need to know to effectively go cruising. It was amazing to see her go from absolute zero to a sailor in one week (well with a little book study before you show up)
 

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There's also a school in St. Petersburg, FL that is reasonably priced, keeps their boats very nice, and is in a great area for sailing (at least, I think so). Here's their website...
Florida Sailing School

If you're really set on someplace in the Caribbean then Sunsail has a sailing school based out of Tortola and The Bitter End Yacht Club does lessons from their resort on Virgin Gorda. Neither will be extremely cheap, but both are in beautiful locations with really nice facilities.
 

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If you have learned to fly a helicopter you can learned to sail a boat. You are not going to show up without reading the Flight Manual or SOPs. Likewise it does not make sense to spend a ton of money for a school without being prepared. You could probably learn a bunch and pass any test by just showing up, however if you are more knowledgable when you show up you should be able to pick up more of the advanced stuff during your class.

I'd suggest a really basic sailing book just to get started in sailing theory, then Annapolis Book of Seamanship.
Amazon.com: annapolis book of seamanship

If you have made it through military flight training you should be able to teach yourself how to sail.
 

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Discussion Starter · #20 ·
That you all for the great advice and links. I am just going to dive in, head first. I have about 7 months to study, so I should be an expert on theory before I ever set foot in a classroom. The blog of Katie and Jessie is quite motivating. I am really excited to get out there. I will be sure to update this with my results.
 
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