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Old 02-10-2020, 14:48   #1
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Critique my 5-year plan

Hi

"Long time reader, first time caller" and unsure to which forum this thread should be posted. So apologies if its in the wrong place.

So, like many, I've had a decades long dream of retiring and doing some liveaboard cruising. No grandiose ideas of a circumnavigation, my plan was 2-5 years swanning around the Carib (although my gf 29 years my junior just asked about Atlantic crossings so who knows).

I have "some" sailing experience. Dingy as a kid, crewed here and there on "round the beer cans" racing Catalina 29, have ASA 101, 103, 104, 106, 114 and a few bareboat charters in FL and Keys. Turning 55 in the spring, and planning on pushing away from the docks at the start of cruising season when I'm 60. Other slightly relevant experience is 30+ years of aircraft ownership, instrument commercial pilot (I flew airshows, low level formation aerobatics, not airliners), thousands of no-accident hours, and I'm a Turbo Porsche modification mad-scientist (think 1.21 gigawatts is enough).

How do I prepare?

We (gf and I) will be doing (and in my case re-doing) the ASA training in the next 6 months. The plan for the cruising vessel (no, not a '69 Buick Skylark) is a Catamaran in the high 30s to low 40's size (Lagoon 380S owners look nice) but for giggles I just tried to get insurance quotes and they ranged from $10k/year to "sorry no coverage available" so I assume some "big boat" ownership experience is needed.

Here's the plan then. Along with the training, do a couple of bareboat weeks or fortnights in the next 1-2 years then pick up a "biggish" monohull. Something in the 35-37' range and stick it on a mooring or slip in FL somewhere I can get to in around 2 hrs flight time from ATL. I'm thinking something that's "ready to go-ish", ie doesn't need immediate work or upgrades, and something that I can sell readily in 3-4 years to buy the final vessel. Then spend weekends and some weeks on the boat building time. Do the maintenance, but hopefully not put too much into it, sell it for a smallish depreciation and buy the appropriate catamaran 6-12 months before departure and spend that time upgrading as necessary as well as learning to sail her.

FWIW I'm a very hands on guy, I've maintained my own aircraft for 30 years including engine tear downs, done several full up panel/electronics re-fits, and have become rather an expert on maintaining/modifying mid-80's Porsche 911's engines and fuel systems, and an electronics/microcomputer hobbiest and use those skills to modify the ancient Porsches. So, while I don't have direct boat maintenance experience I'm not afraid to dig in. I'll pull a motor without fear, do electronics/nav systems installations etc, just can't weld.

So, at a high level, is my plan "on course"? What advise would you give me? And for those sailing in FL, east coast or west coast?

FWIW while I'm not Bill Gates, this is fully budgeted and I'm a cash buyer so no boat loans needed, not a relevant discussion (slip fees on the other hand...)
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Old 02-10-2020, 15:16   #2
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Re: Critique my 5-year plan

1) Split the pan into small chunks.


2) Place the chunks on a realistic time-line.


3) Start grinding at it, and ticking off the chunks.


4) Re-visit, and re-order, the remaining time-line once a month.


Reload. Repeat.


Done.


In my book: 5-year plans are bloody long range plans. I only make 5-day plans. But I am decent of turning them into 5-day realities. ymmv



b.
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Old 02-10-2020, 15:26   #3
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Re: Critique my 5-year plan

These threads never get much traction here...the thing to do is walk the docks...go to marina's...talk to boat owners on the water....charter a few boats, read some books, watch any of countless Youtube video's, etc....here it's just talk....every poster will have his or her opinion, none of which is likely to benefit or sway your thinking...as it seems you pretty much have your own game plan in mind...

Time on the water is your best teacher...and it will determine what you "might" actually do....
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Old 02-10-2020, 15:50   #4
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Re: Critique my 5-year plan

The plan is fine, get a boat and go sailing. Everything else is just details.

I do feel getting the intermediate boat is a waste of time and money.
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Old 03-10-2020, 06:08   #5
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Re: Critique my 5-year plan

If the five years is because that is when you retire, then spend it sailing as often as you can. Whether it's on a boat of your own, lessons, a coop ownership, or other people's boats. Just get out and sail. Ideally on many different boats.
Once you close in on retiring, a year or two out, start looking for "the" boat. At that point you will have way more knowledge and experience and have a better idea on what you want.
The year or 2 will give you time to get to know her and do a shakedown. By the time you retire, you can cast off in confidence
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Old 03-10-2020, 07:52   #6
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Re: Critique my 5-year plan

Quote:
Originally Posted by sailorboy1 View Post
The plan is fine, get a boat and go sailing. Everything else is just details.

I do feel getting the intermediate boat is a waste of time and money.
I'd like to discuss that a bit more

"The" (current) target boat is a high-30 foot to low 40-foot cat. Cursory glances as various add puts that in the $200-250k range lets say. Add on that the slip fees which are going to be much more than a comparable LOA or shorter monohull.

Add to that the risk that, hey, we might not like this after all.

and the biggie. As I mentioned I got some insurance quotes on that boat, and they ranged from astronomical to not available. Principally because from what I gather, I have no big boat ownership history.

So, several reasons for the intermediate boat:
1) Gives us the ability to build time on the water without a $200k+ investment. I'm looking at $75k monohulls right now.
2) Gives us the ability to test the waters at a much lower entry point, so a lower risk and opportunity cost should it not be for us after all
3) Gives me some opportunity to "re-tool" some of my plane/car mechanic skills to boats at a lower cost
3) I can insure it now

I'm curious why you think its a waste of money? Do you think the depreciation over say 3 years would be significant enough to offset those points? Do you think the intermediate won't sell quickly enough?

Thanks
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Old 03-10-2020, 08:02   #7
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Re: Critique my 5-year plan

Best advice I ever received ? ‘Buy the biggest boat you can afford, and go now.’
We did exactly that with zero regrets.

PS - shop around for insurance, the quote you refer to is ridiculous. We pay $4000 pa for $700k of boat. I’m not in the States.
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Old 03-10-2020, 08:14   #8
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Re: Critique my 5-year plan

Quote:
Originally Posted by barnakiel View Post
1) Split the pan into small chunks.


2) Place the chunks on a realistic time-line.


3) Start grinding at it, and ticking off the chunks.


4) Re-visit, and re-order, the remaining time-line once a month.


Reload. Repeat.


Done.


In my book: 5-year plans are bloody long range plans. I only make 5-day plans. But I am decent of turning them into 5-day realities. ymmv



b.
Yep. Done.

0-6 months, get trained/re-trained through ASA 114
6-18 months, 2-3 bareboat weeks
18 months, sell hotrod/buy intermediate boat
18-months - 48 months, sail it, tinker on it, stay on it
48-54 months sell it, buy next boat
54-66 months, sail it, configure it as needed
66 months, see ya!
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Old 03-10-2020, 08:17   #9
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Re: Critique my 5-year plan

Quote:
Originally Posted by Hartings View Post
Best advice I ever received ? ‘Buy the biggest boat you can afford, and go now.’
We did exactly that with zero regrets.

PS - shop around for insurance, the quote you refer to is ridiculous. We pay $4000 pa for $700k of boat. I’m not in the States.
I can't go now. I have an elderly parent to take care of for probably another couple years.

You insurance #'s seem more in line. I'll shop some more. tks.
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Old 03-10-2020, 08:21   #10
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Re: Critique my 5-year plan

Cruised my whole life (Med and Carribean). Sailed a lot but at 60, I switched to trawler. Cats are great but sometimes a problem to find dockage. I owned center-consoles, a mono- hull, a cat PDQ and chartered many, and 3 trawlers one of which I had built with my design. It is important to know one's limitations. Unless your GF is a body builder, consider the advantage of some luxury. On a good trawler designed like a sailboat (solar etc...), 1,000 gallons go a very long way. (I am a commercial pilot too, and owned a 912 chromed engine, and 911...)
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Old 03-10-2020, 08:22   #11
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Re: Critique my 5-year plan

I would also skip the intermediate boat. You’ll spend a lot of money for little return. I would charter or crew as many boats as you can. Take some trips to exotic places and charter models that you might want to buy. Crewing with experienced captains will help you develop practical skills quickly. These trips will change your opinions about the size and type of boat you want to buy and where you want to go sailing.
Then, about 2 years out from when you want to start sailing, start shopping and buy the boat you want, better informed by the experiences you’ve had up until then. Then spend time and money to get your boat ready.
Enjoy 😀
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Old 03-10-2020, 08:22   #12
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Re: Critique my 5-year plan

I agree with the go now if you can. I retired early, as my dad had passed away young...
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Old 03-10-2020, 08:29   #13
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Re: Critique my 5-year plan

Younger you do it the better it will be as cruising can be hard work at times. Florida east coast will give you easy access to the islands. And remember it is a long way from Florida to the Caribbean and not an easy sail from the Dominican Republic to Puerto Rico. Buy the Thornless Path.
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Old 03-10-2020, 08:29   #14
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Re: Critique my 5-year plan

I am also skeptical about the intermediate boat. For the cost of the boat, insurance, slip fees, etc., you can do a whole lot of chartering. That gives you the chance to experience a lot of different boats, and learn what matters to you. If you go with smaller charter companies and stay away from the sailing meccas, chartering is pretty affordable.


Selling the intermediate boat is guaranteed to be a pain. Boat transactions always are.
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Old 03-10-2020, 08:41   #15
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Re: Critique my 5-year plan

Quote:
Originally Posted by flightlead404 View Post
....I'm curious why you think its a waste of money? Do you think the depreciation over say 3 years would be significant enough to offset those points? Do you think the intermediate won't sell quickly enough?

Thanks
I agree it's a waste of money*...but let's use an airplane example that you've seen many times to see where your philosophy is at.

So you're introduced to a banker who wants to become a pilot. He's read about planes and ultimately wants a Bonanza, but isn't sure if he should buy a starter plane, or go straight to the Bo.

Starter-plane advocates say "start cheap, maybe you won't like flying, 172 parts are cheaper than Bonanza parts, 172s are more forgiving, etc, etc." Go big, go early Bonanza first advocates point out that Lufthansa solos (or used to) their ab initio pilots in Bonanzas (clearly with top/comprehensive training), and that...if you start with a starter plane...invariably you're going to do a lot of physical labor and $$$ in parts "making things right" on your Cherokee....hours/$$$ that you won't get back on sale when you sell the Cherokee to buy the Bo....so why not just get the Bo in the first place such that those same hours work/$$$ fixing your plane results in a more pristine Bonanza. In other words, why effectively 'bring up to your snuff' two planes instead of just 1.

If you're very disciplined to buy a starter boat and not muck around dumping money (saying nothing about time) into fixing every this and that (which I assume pilots are prone to doing)...then perhaps a starter boat isn't a waste of money.

*If your starter boat is a $15k boat (Cherokee equivalent) with good rigging, sails, engine, and fuel tank...then I think you'd be okay with such a boat. On resale this would be easier to flip and/or if you re-sold the boat for $10k for a quick sale you're only out $5k. Buyers of $75k boats are more like Bonanza people who don't want to hear excuses and/or they'll insist on talking you out of more than $5k when you go to sell.

Otherwise, I'm not sure if you've been in Cessna 150 lately, but they're a little harder to fly than a 172. You've got to pay a little more attention, fly the wing more than rely on thrust, and they get pushed around more...which is sort of fun, more pure. I'd suggest that the same applies to boats...if you're going to get a starter boat, consider going smaller than you think you'd like. This may not impress the crowd but I'd suggest it'd be more fun, and frankly cheaper if you buy right and resist the urge to 'upgrade' stuff while figuring out your final boat solution.
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