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CaribbeanDreamer 05-06-2008 11:42 AM

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.

JohnRPollard 05-06-2008 12:38 PM


In theory there's nothing wrong with your plan. In fact, it's not particularly novel -- plenty of folks have done, are doing, or intend to pursue a similar plan. So much so that "the south seas" are getting a bit crowded (at least, the anchorages anyway) in the opinion of many.

But in reality, "life is what happens when we make plans" (paraphrasing John Lennon). So my advice would be to focus on the short term objectives, and remain flexible with respect to the long-term goal. Think baby steps rather than giant leaps. Your "event horizon" is a long way off, and the best way to make your dreams come to fruition is to focus on near term objectives like improving your sailing and navigation skills, and developping a sound financial plan to fund your distant dream (for planning purposes, assume that it will cost you more than shoreside living/retirement).

We seem to get a lot of folks (many non-sailors) who show up here on their first post and announce grand plans to sail the world, so forgive me if my reply comes off a bit jaded. We often never hear from them again, too. So stick around, read and learn, ask questions. You may find a lot of helpful information here, and along the way on your journey you may decide that your plans need to be adjusted -- scaled back or, who knows, maybe enlarged!? No harm in that.

Welcome to SailNet!

P.S. You're in a great location to spend summers building experience aboard your starter boat. Many beautiful cruising grounds -- heading both north and south -- within easy distance of Boston. Here's a thread that talks about various daysail destinations: Link

sailhog 05-06-2008 01:23 PM

I'll second Cap'n Pollard.

People manage to cruise the world after decades of hard work and years of preparation. But it ain't easy, and frankly there's something about the tone of your post that sounds a bit pipe-dreamish to me... Somebody on this forum once said "You have to EARN the right to cruise." My sense is that you might think the process is easier to do than it really is, that things will naturally fall into place and one day you'll wake up in paradise with a boat in the backyard. I've had the same dream, and in five years I've made it from northwest Colorado to Hilton Head Island with a 28-year-old Catalina 30 parked twelve minutes away by bicycle. Ain't the South Seas, and it isn't a big boat... but it's a move in the right direction.

christyleigh 05-06-2008 02:10 PM


Originally Posted by sailhog (Post 310242)
I've had the same dream, and in five years I've made it from northwest Colorado to Hilton Head Island with a 28-year-old Catalina 30 parked twelve minutes away by bicycle. Ain't the South Seas, and it isn't a big boat... but it's a move in the right direction.

Right direction.... heck... you're at the end of My 6 Year Plan :rolleyes: To go from the freezing cold a hundred miles from by boat to 'living the dream' that you already have :)

CaribbeanDreamer 05-06-2008 02:33 PM

Nice feedback, and I have to agree with everything said. My dreams are in technicolor, but I always remember a poster I saw my first day of school back 40 years ago of a little ant next to a big piece of cake, and the caption "You'll never know how much you can eat until you bite off more than you can chew".

To Sail Hog and Mr. Pollard, while I admit that the full realization is a log way off, I am hoping that the voyage there is as much fun as the destination. 10 years or so could find me crippled, or dead, or living in Arizona with no water in sight... However the way I see it, the 10 years of learning is also very pleasant. I get to have a place to go on nice summer days, Sail Boston harbor, get used to the waves, and everything else. Maybe I'll hate it. I remember as a kid the saying that the two greatest days in a boatsmans life is the day he buys it, and the day he sells it. Who knows...

I guess I just need direction for now... I have a little Fiat X1/9 project car that I put up for trade to see if I can get my first boat on the cheap, and within hours got a reply from a guy in the cape who has a Classic 19 Bristol. Maybe it is a good jumping in point since I can trailer it and launch it about 4 blocks from my house at the public landing when I want to go out on the water for the first little while.

So from here, if anyone has any direction for me to point myself in, places I should go for info, things I should do or plan to do over the next X years (I like the idea of crewing with some experienced folks to see what it's like on a longer trip).

Anyway, glad I found this place and I take everything said to me on this very seriously. I have a goal, but part of that goal is the act of traveling to it.


JohnRPollard 05-07-2008 06:11 PM


Always good to have dreams! Like I said, you're in a good location to begin working toward realizing them.

As for the Bristol 19, I would suggest starting a new thread in Buying a Boat, with "Bristol 19" in the title line. If someone has info they'll be more likely to notice your question that way. Also, consider searching the archives, as there may already be info about this boat ( am I correct that the Bristol 19 and the Cape Dory Typhoon share the same hull, or am I confusing it with another model?)

buckeyesailor 05-07-2008 06:26 PM

Holes?......what holes?........I don't see any holes.....

Sounds like a solid plan to me.......whilst taking heed to the above advices.

I've got 7 months left on my 8 Yr. dream (originally 6 1/2 Yr. plan)......and worth every single days wait!

Welcome and Good Luck.......

CaribbeanDreamer 05-27-2008 10:26 AM

Thanks to everyone for their great comments... I'm slowly moving ahead with my plan, and adjusting it to "be careful and respectful of mother nature and the oceans around me".

I'v also looking at a 1971 Islander 23 which is in decent condition to start, and has a trailer so I can avoid mooring charges for a little while.

Hope to share a drink with some of you planners in the islands one day. Be good, be smart, be safe, and be well. Enjoy today in a way that you won't regret it tomorrow and we will have a much better chance to share that drink :-)


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