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The maximum size should be based on your physical strengths.
In sailing, bigger is not always better and in most cases the usual progression is from small to larger for the following reasons:
Sailing is acquired skill. The smaller the boat the faster the 'motion', the faster the reaction, smaller loads on winches, lines, sails etc. etc. etc. A larger boat will have much slower reaction times, greater loads on winches, sails, etc. ....
Your 'learning curve' will be exponentially faster on a smaller boat as on a big boat with very long drawn out reaction times (inertia), sluggish but more powerful forces involved, etc. etc. and without the 'experience' learned on the smaller boat will many times 'cloud the fact' that you are in deep doo-doo and without knowing it.
The usual 'progression' is to start with a lightweight dinghy type with a centerboard, then move up to a deep keeled boat on moderate length (24-30 ft.) and then when 'satisfied' and so skilled then move up to the big boat. As an example, if you misjudge your approach to a dock with a dink, it will merely bounce off - and no damage done to crew and boat; with a little heavier boat you may break or 'chip' the hull and someone on the boat may fallover and get hurt ... on a big heavyweight boat the possible result may be destruction of the dock, severe hull etc. damage and crushed passenger etc.
Suggest you start small and rapidly build your skills by 'plateaus' and when each is reached then move to the next step. All too often folks will start with the 'ultimate' big-boat, get the hell scared out of them ... and for the rest of their entire 'sailing experience' have a 'dockside entertainment center' permanently terror-tied in a slip, etc.
Suggest you consider to start with a small but sound 'beater' with decent resale value .... rapidly gain the skills and 'progress up' through all the 'beaters' until you arrive at your final goal.
Cheaper and Faster .... and SAFER.
Airplanes: ... you dont begin your flying in a multiengine 747 jet.
Automobiles ... hardly anyone you know has ever 'started' their experience in a Ferrari or Corvette or 18-wheeler.
BIG boats get boring real fast for children and the smaller the boat the faster the small child will learn too. If your children get bored on a boat ... you wont have that boat very long.
So, the maximum sized boat should be selected based on the maximum amount of fast and precise work you can do in an emergency - example: having to manhandle the largest water-soaked sail on a vigorously pitching deck in 'storm conditions' because the sail 'has to come off NOW' and get stuffed down below ... as you are being washed by waves coming across the deck as the bow is plunging under water ... and for the average, middle aged and in perfect health adult - that equates about a 400 sq. ft. sail and this equates to a boat thats 35-40+ ft. Of course you would reduce such risk by gaining the proper experience, etc. in 'smaller' boats because you would of past experience gained would have foreseen and thus prevented the emergency 'cluster festival'.
Last edited by RichH; 02-08-2011 at 01:34 PM.