Join Date: Feb 2000
Location: Annapolis, Md
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This has been one intensive discussion full of a lot of worthwhile advice. I have to agree with much that has been said here. Get the basic courses under you belt, try to get a year or so under your belt sailing a light responsive 23 to 26 footer to develop good sail trim and boat handling skills, buy a 7,000 to 11,000 lb, 32 or so footer, work on getting into good physical shape(As a 53 year old that routinely single-hands my 38 footer, I find yoga extremely helpful in that regard in that it builds strength, flexibility and balance, all three of which tends to go with age)and go cruising.
A couple quick suggestions to add to this discussion, I would try to size your boat by displacement rather than length. While I must sound like broken record, as boat get up in weight, they become harder to handle. It is weight not length that determine the size of the sail plan, the loads on the lines,the energy required to sail the boat, and the amout of gear and supplies that you can carry etc. Within reason longer boat of the same weight will be easier to handle, more seaworthy, have a more comfortable motion,and be faster than a smaller boat with the same displacement. Boats like Flicka''s and Dana''s can really wear you down despite their small size.
I keep seeing people recommend a cutter rig for single-handing. That is nuts for the size boat that you will ultimately end up with. There are few bigger pain in the butt to sail, grind you down with each tack, overly complex rig than a cutter rig on a small boat and frankly when you talk about boats in the size range that you are considering there is absolutely no advantage to a cutter rig and the disadvantages are huge.
I strongly suggest that you try to find a fractionally rigged sloop. Most times the working jib on a fractionally rigged sloop is the same size as the staysail on a cutter and so serves as both your working jib in normal conditions and your staysail in a blow. Because the headsails are smaller in size they are easier to tack and cheaper to maintain. Unlike a cutter, you are not dragging the headsail over a jibstay so tacking is much easier. Fractional rigs are easier to depower without having to reef and as someone who is single-handed on and off for almost 40 years of my life, words cannot tell you just how energy saving that can be.
Make sure that the boat you end up with has all of the halyards and control lines lead back to the cockpit so that you can adjust halyards, outhauls and tie in both reefs without leaving the cockpit.
And lastly, I want to encourage you heartily to pursue your dream. You have plenty of time (my Dad is 77 and still going strong) but you do need to move with a sense of purpose. On the other hand, you don''t need to be so goal oriented. When you get out there, you may find that solo cruising is the reward unto itself and that going around the world is the kind of directed goal that is the antithesis of what voyaging under sail is all about. There are few things in life that are more profoundly moving, than to be underway with only your own skills and abilities to guide you. There is an aesthetic to being alone, except for your boat and the sea, that cannot be duplicated in any other way that I know of. There will be times when you will be lonely and wish there was someone along to whom you could say, "Hey look at that!". But there is an incomparable introspective beauty to living with only the beauty of nature, and your own perceptions of the world around you. To me that type of thoughtful solitude is the greatest luxury that one can find in our sometimes crazy world.
(On the other hand, I am very much a people person and love meeting new folks in each port of call.)