Re: Sailing "big boats"
We sail 44 ft.
For us the biggest issue is really haul-outs - and it's not about cost which is only marginally more expensive.
When in the South Pacific or any other wide cruising area (perhaps the Caribbean is the same) if you have a problem that requires the boat to come out, there will be nowhere in the islands that a 50 ft boat can be hauled out. Even at 44 ft we're marginal and many places are not equipped for this.
As for sailing 44ft, I have over the years upgraded from 26 to 33 to 36 and now to 44 and I can't say I have any issues managing the bigger size. Whilst I have no intention of going any further up in size (this boat is my last), the prospect doesn't frighten me.
Certainly I would not sacrifice the comfort of our boat for the alleged ease of handling something smaller.
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