Setting sail in your own sailboat and voyaging across the many oceans of our planet and visiting the myriad fantastic destinations en route is the easy part of your adventure.
Planning ahead of time to get it right is the more difficult of the two, so you need to begin well in advance of your actual departure date. Depending on your own situations, that period could be months or even years. No matter what your time frame is, the more detailed your planning is, the better you will cope with all the situations that the sea, Mother Nature and human elements will throw at you (and they will) during your odyssey. In the event you will be amazed at the variety of events you will encounter along the way. They will range from the fantastic to the bizarre, monotonous to exhilerating, scary to exciting, and sometimes downright challenging. This is all part of the experience, but in the main these experiences will be wonderful and uplifting and once again you will surprise yourself at just how simply, many adversities you will overcome with your own gathered knowledge and ingenuity.
An 'Old Salt' once said to me when I was in the early stages of planning my odyssey: 'You may not be fully qualified/experienced when you set sail for the first time and leave port, but you sure as hell will be whenever it is that you return!'. Never truer words were spoken and I can assure you that the unbelievable storehouse of knowledge and experience that you will build during the time you are away will be a constant source of amazement to you and on which you will forever be able to draw upon.
So, now is the time to begin. It does not matter whether you actually own your own sailboat yet, that will happen as part of the process. This a good place to start - draw up a thoughtful and lengthy list of your criteria for the sailboat of your dreams.
A few headings could be:
Class - sloop, ketch, schooner etc.
Size - length, beam and draft.
Keel - long, deep, bulb, retracting etc
Deck layout - aft or centre cockpit, single forestay, cutter rig, running backstays etc.
Cabin layout - how many berths, master cabin fore or aft.
Electronics - radar, GPS, plotting, hf radio, computer with weather software, and now, AIS.
These will keep you busy for a time.
Depending on the level of your sailing skills, you can take any number of sailing courses, however, make sure they include more practical sessons than theory - you can read all the books on sailing technique etc. in the world, but nothing beats getting out on the water and putting sailing miles under your belt. Go down to the local sailing club and get yourself a regular crew position on a club racer.
If you live by the water you can buy a small and inexpensive sailing dinghy and get all the fun and experience you can poke a stick at.
Then you can go on and book yourself into a 'safety at sea' course.
Also, during this time, book yourself into a local 'First Aid' course. From my own experience of a crew member fracturing a couple of ribs mid Pacific, I can tell you it is invaluable knowledge to have. It will also assist in deciding the make up of your medical kit.
Next, study navigation. With all the electronics nowadays, this is an area that tends to be left aside more and more, leaving the electronics to take care of it. This fine as they do a wonderful job, but what if they all go down for some reason? lightning strikes, knockdown, flooding or other damage. You need to have navigational skills to be able to navigate if this adversity strikes. Also, include a course on astro navigation as this is a marvellous feeling, when mastered, being able to use a sextant and make a plot within a nautical mile or two of your GPS readings.
You will need to take a course and get your ticket for HF radio. Along with this you will get call signs etc. for your boat.
Get a two metre length of supple line from your local chandler and set it up on a convenient bar/rail at home somewhere - in your office, the bed end, back of a chair and constantly practice your knot tying until you can tie them automatically. The knots you will use the most will be bowline, clove hitch, fishermens bend, rolling hitch - become proficient at these and as many others as you can.
Study charts and all their markings, buoys, rules of the road and ships lights.
Flags of all nations is a fascinating subject, along with nautical flags and what they mean.
You are going to be busy fitting all this in and my suggestion is to start as soon as possible and get as much out of the way prior to actually purchasing your dream sailboat. As your 'set sail' date moves closer you will find a myriad other things need your attention and it is easy to put learning some of these other skills aside - so get as many under your belt as you can well ahead of time.
Finally, when you do have a few minutes to spare, read any sailing material you can get your hands on and especially don't miss 'Sailing Alone Around the World' by Capt. Joshua Slocum.
Good luck and exciting and safe sailing.
You can read much more about cruising and passagemaking in my ebook 'Voyage of the Little Ship 'Tere Moana' downloadable from my website http://www.sailboat2adventure.com/