Over at one of the forums I check out from time to time, there is a discussion about sailing from Florida to Puerto Rico in a small boat and most of the discussion is of the "why you should not" rather than the "go for it" sort... Which is odd, as the forum in question is called "Sail Far" and not "Ship it down"!
Of course, a lot of the reasons brought up are valid on one level but they all seem to leave out a few very important points...
Experience... The guy wanting to go does not have any blue water miles and while it makes sense to get some experience, the only way to get some blue water experience is to do some blue water sailing.
The boat is too small... Well, not really. It is small but seaworthy (it's a CAL20) and more than capable of doing the voyage and it does happen to be the boat he has which is no small factor in the decision making process.
The voyage will take too long... Well, it is a sailboat! All voyages take too long and it is simply part of the gig and certainly not a deal breaker of note.
The reason I mention all this is simply whenever you bring the decision making process to a group the system will always bog down and either become a negative or worse simply wind up in a stasis situation. Over the years we have noticed it time and time again when groups of cruisers found themselves ready to set off on a passage the tendency was to sit and wait for better weather, smaller seas, or some other undefined need that was simply never going to happen... Meanwhile, the cruisers not part of the group or on the fringes would simply pull up their anchors and quietly sail off into the sunset.
The same problem arises in danger situations (Danger! Danger! Will Robinson!) like approaching hurricanes or suchlike. Folks sit around talking about whether they should run for cover, haul their boats, or other proactive acts. As they sit, the storm comes nearer and nearer... Again, those not into the whole decision-by-committee thing run off to the mangroves, put out lots of anchors, and wait in relative safety as the others find themselves in stasis.
Getting back to the question of whether this guy should sail his CAL 20 down to the Caribbean... Well, it all depends. The real question is does he WANT to sail his boat down and is he willing to do what it takes to make it happen?
If he does, well he can always pick up some blue water experience before going down as there is always someone looking for crew and the only way to get experience is to go sailing.
Whether such a voyage is right is more about what is right for the man in question and only he knows what the answer is...
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