Sell everything and cruise the caribbean, really?

I feel like I see that with some of my peers, the whole who cares about me when I'm 50/60/70+ I'm young and need to experience it all today. Who cares about long term tanning negatives, I'll look great in my 20's and 30's or who wants to save for retirement, I'll just work my whole life so I can travel and dine now. Nobody should live like a total pauper if they can help it but after watching some of my friends work for 5 years that whole "I don't mind working forever" thing is starting to wear off and maybe GreenCheese isn't a total fool for suggesting that they contribute to an IRA...
 
H

I think this really comes down to this: Remember the old ant and cricket cartoon:confused:



Plan A: Work 35 years, build a nest egg, and hope you are still alive and healthy enough to cruise the Caribbean when you are retired and old.

or

Plan B: Sell everything, buy a boat and cruise the Caribbean while you are young, dumb, and full of... energy...Then, worry about retirement when you are older.

The sad thing is that for much of the rest of the modern world there is option C: Work hard at your job and then use your four to six weeks of paid vacation each year to sail the Caribbean, etc.
 
keep turning left

My favorite sailing vlog is

Keep Turning Left with the accompanying youtube videos. The business model is quite different than a Patreon account.

Very entertaining fellow, but not exactly the Carribean.
 
Im 52 and checking out in 5 and a half years at 58. Come hell or high water. Since I'm a boater, I'm good w/ the high water.

Yeah, on your Tenn-Tom trip, stay on the Tenn River and joins us for a fall weekend with the Volunteer navy.

There's a fully supported group PWC (WaveRunners and SeaDoos) trip I plan to take in June that traverses 600 miles of the Tenn River over a week. I think they have about 100 riders each year. Great way to see the state by waterway.

Maybe I'll Vblog that trip, post it on Youtube, and ebeg people for money....

You'll come right by my lake house on Lake Wilson in Florence, AL. That's quite a sight to see so many PWCs in one place.
 
The sad thing is that for much of the rest of the modern world there is option C: Work hard at your job and then use your four to six weeks of paid vacation each year to sail the Caribbean, etc.


If you ever get that much.... I interviewed with a firm and the max vacation was 2 weeks... I was told it was 1 week the first year and then went up to 2 the next.... so I asked 'when does it go up again?'.... the guy talking to me said he had been there 20 years and he still had 2 weeks....

Heck, IIRC, my last job would have only been 2 weeks!!! But I negotiated 4 when hiring on...
 
My favorite sailing vlog is

Keep Turning Left with the accompanying youtube videos. The business model is quite different than a Patreon account.

Very entertaining fellow, but not exactly the Carribean.
Just skimmed thru one video, but the production quality was excellent. I'll have to give more episodes a go. Thanks!
 
If you ever get that much.... I interviewed with a firm and the max vacation was 2 weeks...

One of the perks from megacorp was 7 weeks of vacation plus a whole bunch of paid holidays. (I think there were 14? It included the days between Christmas Eve and January 2nd.)

The new folks still have a pension plan and retiree healthcare, but their vacation plans top out at 4 weeks.
 
Not that many of these people aren't just dreaming, but rather than working 35 years first, working 10-15 years and saving your money will give you the chance to work boats in the tropics. I suspect that they probably clear about enough to keep up with basic living expenses.

My personal fun for boating is tallships, and while they won't make you rich, it will basically include room, board and cover your bar tabs. It was fun in my early 20s, and I may go back when I hit 40. Sure, I won't be saving anything... but I'm not going to be spending more than I earn either, and when I have close to $1M invested, that "fun" living hand to mouth isn't doing such a bad job in terms of buying my investments time to grow. If I do fall off the mast and can't do it, there is enough that I'll never starve, but I'm still young enough to enjoy it properly.

Since November I've had 3 co-workers under 65 die in the last month, plus an uncle under 70. I'm still under 40 for a couple more years, but I am not going to be sentenced to die in the harness. If it means a little more risk while I can still take it, and having a lower SS when I hit 70 so be it.
 
Well, they are just giving up one job for another. Video production and boat repair. About a week on a boat is all I can handle. It is a great way to see some parts of the world, but, not going to be a way of life for me.
 
We would fall into the category of old dreamers! I'm reading this from aboard our sailboat in Green Turtle Cay Bahamas! we spend 6 months on the boat and 6 months in the NC mountains. There are a few young folks and young families traveling by boat (a few working from the boat) but the vast majority are in their 60s and 70s, retired and cruising economically! There would be little demand for any naked videos of this crowd!
 
Not tech savvy enough to do a successful blog let alone a v-blog, so we're just going to cruise around the Chesapeake Bay this spring, then maybe Florida, Bahamas and join some of you guys and do the rest of the loop!
 
There's lots of alternative lifestyles on dry land on Youtube. There's of videos from people living their cars and vans (usually not out of choice) up to folks living permanently in very fancy RVs and Airstreams.

If I was going to "sail away" it would be on land with an F-150, V8 supercab truck and an Airstream Flying Cloud 25FB with as much solar as I could get on the roof.

 
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