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Much good information in this thread already.
I think it was Nathanial Herrishoff who also said of blue water voyaging, 'Get a boat that can take care of you when you can no longer take care of it.'
I suggest you read:
Robin Knox Johnston - 'A World of My Own'
Tanya Aebi - 'Maiden Voyage'
Robin Lee Grahm - 'Dove'
John Neal - 'Log of the Mahina'
All the above were young (ish) people who single-handed boats 32' or less. They did it in a variety of hull designs and with varying levels of experience. While their voyages took place a while ago you will gain a perspective of the psychological aspects of your dream as well as the physical aspect of small boat cruising. I suggested this same reading list to my son who now owns a 27' Watkins, 'Walkabout', and has made a round trip voyage from NC to Bahamas single handing back 5 days in the open Atlantic. He is now in the process of selling the boat to buy another, larger boat, based on his experience on the 27' in order to sail around the world.
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