This 2nd video that I just viewed, is nuts as to
learning anything. Sailing is not a video
game, and not an okole sitting event on your couch twidling thumbs. As mentioned, you need to feel the wind on your face, the heel of the boat, the response from your inputs at the
helm. Look at the water, and the sky, and the clouds and what they can tell you.
Same with flying aircraft, we strongly feel, you need full on instruction in a real plane.
As many here related, you need to be actually out there sailing. I watched that sail away video, and here is what would happen in real life.
The vessel is sailing on a reach, and comes to a buoy, and all he has to do is turn.
Not even close. That is nuts. The boom is out, and not sheeted in before rounding the buoy. I am talking real sailing vessels, not dinghy sailing.
That turn can result in full on disaster. The main sheet is out, and the boom on a real sailing vessel would be swinging over with enough force to dismast the boat, and if anyone on board had their heads up, they more than likely would be killed as the boom with the force of the winds, impacts. the
head . Or the boom sweeping across the
deck, smashes into a body, knocking them over board, with possible serious injuries or drowning.
Add in no mention of cutting the
jib sheet and sheeting for the new tack. The
jib would have been back winded, and the vessel eventually in irons or out of control.
Back to real life:
Your goal is to sail off on your dream of cruising . That is going to take effort, and study and actually sailing on board a boat that has systems to learn , as well as actually sailing. That means being able
dock what ever vessel you sail , under sail .
Why ? Well, engines fail, tansmisions fail,
batteries and
electrical systems fail, etc.
Strongly recommend a structured sailing course, and a great deal of devotion to your goal. That would be learning from a U.S.C.G. Licensed Capt and Instructor with a certified sailing club ( they have the
boats, no huge outlay of cash ), and gaining some kind of a
certification.
ASA is one of the widely recognized organizations. But a lot depends on the individual sailing organization and the quality of the instruction.
Add in coastal piloting, and
navigation, and that means chart reading, and plotting, taking bearings, D.R's, Estimated Positions, Fixes, Running fixes, and much , much more. Plus
GPS.... I use both . We feel the good
skipper applies all different aspects of
navigation, not just one.
Once you pass your written tests and check outs , you can sail the sailing club vessels on your own. Sailing is not driving a car, it is seaman ship, boat handling, wind direction, seas, points of sail,
knot tying,
emergency procedures, weather systems,
fog procedures, even nav by
depth soundings, and the list goes on and on. Man
overboard procedures, etc.
Marine head systems, engines, filters, pumps,
electrical systems,
bilge pumps,
VHF radio procedures, fresh water system. Reefing down properly,
anchoring methods,
single hook, bahamian moors, bow and stern. Plus much, much more. We will never know it all.
Also with a sailing club, generally they have several different makes of vessels, starting at at about 27 ft going up to 50 footers depending on their fleet.
Why is this important, because you will be able to sail these many different vessels and learn what you like and do not like about the different boats, and be able to make an informed decision when it comes down to
purchasing a vessel.
The ocean does not love you, and when in any alien enviornment, air, sea or land, it is important to learn as much as you can, put everything in your favor, and be very serious about your learning program.
Also, learn about skippers responsibilities , which are substantial .... the
safety of the boat, your
safety and the safety of your passengers and crew. No matter what happens, they are looking to you to keep them and the boat safe.
We do not know your physical limitations, and to go out dingy saling on your own and teaching yourself could be extremely risky. You might wish to Learn from the pros, and then get out and sail boats of the type that will eventually will be the type of vessel you will need to live your dream. Aim directly toward your goal.
These are my thoughts from my personal back ground in sailing,
motor vessels and professionally flying real air planes. ( 40 years )
Both of these careers were concurrent. And took time and effort that actually was fun.
Point being : That does not mean that you have to go thru all of that to live your dream, but we strongly suggest in order to
head off on your cruising dream, you put in the effort to learn as much as you possibly can from professional instructors, on board larger sailing vessels, and then get some serious experience sailing on your own . Then shove off on your adventures at sea.
Yep, we feel it takes dedication,
work, time and perseverance and experience to become a seaman, and
skipper .
Of course there are a lot of different views on that idea. It is entirely up to the individual.
I really believe in this famous quote.
Don't dream your life, live your dream.
Re: Learning to Sail with "Sailaway"?
All these things you'll need to know sooner or later, and in my opinion, they're quite a bit harder than sailing because there is not much physicality, or 'feel' involved, just memorization and calculations. Start with 
But at least you'll know how to do everything but the feel of a sheet, and that will come a lot easier then.
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