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Old 05-06-2008
CaribbeanDreamer CaribbeanDreamer is offline
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6 year plan over 15 years

I grew up sailing lasers, and tanzers on lakes, and still do from time to time. Recently I lived on a marina and all of the boats there got me thinking about retirement in about 15 years. I had been thinking about getting a little place in the Caribbean, but I came up with a new plan which I submit here in order to have holes blown in it that I can better patch now than later...

The plan as it stands is the following:

Over the next year I want to study as much as I can. Study the boats and market out there and some of the book smarts I can get about sailing in salt. Next spring I would put myself in the market for something of a used weekender, 23 to 30 feet over all, and use that as a jumping in point, and training. There is a constant supply of what seem to be reasonable older boats in this range in Craigs List for anywhere from $2500 to $10K. In a worse case scenario, the boat serves as an urban cottage where we can go to escape the city just a little bit from time to time, and I can always putt putt around boston harbour under engine power.

My idea is to spend the next several years cutting my teeth on this boat, and MAYBE one upgrade. I would slowly expand my sphere of competence to allow me to sail down to the cape from Boston, then maybe up to Nova Scotia, or around to the gulf of St. Lawrence if it is navigable by someone like me, and down to New York, Virginia etc...

I figure I have 10 to 15 years before retirement, when I basically sell everything I have, house, furnishings, car, what ever, and find myself a nice 40-45 footer to head due south. I'd probably spend the first year living aboard locally in order to properly outfit / upgrade it if required (solar power, customized interior, various other little long term perks). Set it up to carry a couple of bikes for land travel where ever we go, and enough space for all the bermuda shorts I own, and a bar for the requisite cocaktoo ;-)

Considering the size of my house, I would probably have more space on a 40 foot boat, so closterphobia is not an issue. Ive loved on water all my life, although I've been under power more than under sail, I don't see making the sea my residence an issue unless I find myself living under it!

I have above average intelligence, I am very technically astute. Navigation and communications should not be a complicated issue for me, and seeing as technology is streaming ahead I figure it should be a no brainer by the time I am actually ready to head south. Although I would still study the backup methods, since nothing is for certain.

My thoughts are 7 to 10 years of sailing around the south seas should put me in a position to then find a nice little place where I can live out the last of my days in peace after selling what I have in the boat.

So is this a pipe dream, or is the time frame reasonable for what I plan. I am hoping that by the time this happens, I can actually hook up with a few others that have the same ideas and we can travel convoy style. Something like the mobile home convoys we see on the roads, but with a much smaller carbon footprint ;-)

I look forward to hearing from the true sailors among you, and the dreamers like myself. The sooner I see the holes in the plan, the sooner I can make sure that they are filled!

Thanks folks...

PS, I expect to have a crew of at least two... My S.O. while not committed to the dream is willing to at least explore it with me. By the time this actually happens, who knows, I may just find a few old guys like myself that want to retire the same way and crew the boat that way.

Last edited by CaribbeanDreamer; 05-06-2008 at 11:38 AM. Reason: Just a PS
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