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post #1 of Old 08-18-2013 Thread Starter
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Go bigger or go now?

I am 57 yrs old. I own a 28' S2 I have sailed to Marsh Harbor, Abaco and left there for awhile. I want to continue sailing south ( I mean far south)till I get either bored or too scared. HOWEVER, I do think a bigger boat might be a good option for me, not too much bigger, still small enough to single hand.
So, what to do...........
I've sailed the S2 for 22 years and practically rebuilt her and know just about all there is to know about her. She is PERFECT for the shallow bahamas waters (3'10" draft) and capable of handling bigger water by watching conditions. Her actual value is very little and would probably take forever to sell even though she is registered in the Bahamas (a big deal). OTOH, her loss due to a storm or whatever would not cause me any financial problem at all (would actually save me money) but pride (and loyalty to her) makes me do all I can to keep her safe.
28' does not often seem small until you are at sea. However, whenever I pull into a marina full of huge boats and I know I go places they probably never will because they simply owe too much money, I always hear them remark about how small my boat for being able to get where I am. Not sure if this is a remark on my sanity or their frustration that they should have gone cheaper and simpler. I also know my maintenance costs and marina charges are far less than theirs giving me a lot more possibilities.
Do I continue sailing south taking pride in my spartan accomodations and my little boat that does so much? Will age quickly catch up with me making it difficult to deal with her and make me want a nicer berth? I worry that a bigger boat will have bigger problems and be harder to deal with.

I could buy a bigger boat, a bit of a financial stretch but could pay for something I could rework for my own tastes and make her seaworthy for not much. However, this would take probably two-three years or more and would require me to get familiar with another boat. I'd be 60 by then (seems impossible)

What to do, What to do.
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