Ever feel like quitting the rat race and moving to an island? I do.

[encarter13]

I met a guy in Hawaii named Chicago Mike. He was a bit of a local celebrity. Basically, he cashed out and retired early. Sold his big house in the city of Chicago for lots of money and bought a small apartment somewhere nearby. Instead of buying a second home on an island, he does long-term rentals via Airbnb, Craigslist, VRBO, etc. The way he explained it, he uses his imaginary "mortgage" payment to rent condos and houses all over the world. He is always in Hawaii during the spring and also visit the Caribbean and Europe very often. At the same time, he has the small place in Chicago that serves as his hub for holidays, doctor visits, family milestones/visits, permanent address, etc.

[GB-man]

Holy thread bump but I enjoyed reading it from start to finish.

I met a guy in Hawaii that rented jet skis. Everyday he drove people out to a floating dock in the bay and sun bathed while people drove jet skis around two buoys. I don’t gather he had any money or cared.

[beshannon]

Originally Posted by joeychitwood

Ever feel like quitting the rat race and moving to an island? I do

Every single day

[codecow]

The answer to your question is yes! I think about getting out of this crowded urban area and moving to a much less inhabited spot although still inside the US.

[Kowaco]

Curious What did you do?


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[tyler1980]

Originally Posted by joeychitwood

Ever feel like quitting the rat race and moving to an island?

Have you seen the size and abundance of rats on islands. it's nasty.


So glad on my honeymoon we got an overwater bungalow... the island had tons of them and no way i would want a room in the jungle section

[tyler1980]

Originally Posted by GB-man

Holy thread bump but I enjoyed reading it from start to finish.

and we got another bump

[joeychitwood]

Originally Posted by Kowaco

Curious What did you do?

I bought four and a half acres of pine and spruce trees on a ridge, built a lodge-style house overlooking a river and pond and began a second "career" as a ski patroller in the winter and a mountain bike patroller in the summer at a ski and bike resort. I'm very happy and at peace, but I still dream of looking out over the Caribbean Sea from a porch chair every now and then.

[Blansky]

This is a great thread. I'm glad someone bumped it.

I think about it every day.

But also the saying, wherever you go there you are, can apply as well. Whatever is making you unhappy where you are now, may do the same wherever you go.

I left Canada to go somewhere warm in the 80s. I live in what some would call paradise now, which is wine country of Sonoma County. I'm in Hawaii for a month a year. But still I'm trying to convince my wife Hawaii would be great to live full time.

She thinks as soon as you do that it's not longer a retreat.

We looked at Costa Rica but don't think so. We're not sure about where we'll end up.

I'm between gigs, ha ha, she's still full time.

[CalSRQ1]

Originally Posted by joeychitwood

I bought four and a half acres of pine and spruce trees on a ridge, built a lodge-style house overlooking a river and pond and began a second "career" as a ski patroller in the winter and a mountain bike patroller in the summer at a ski and bike resort. I'm very happy and at peace, but I still dream of looking out over the Caribbean Sea from a porch chair every now and then.

Happy to hear how things turned out for you... no matter where we end up, it's nice to have a vision of that perfect someplace. I live in a resort area people flock for retirement...most of us working here dream of someplace else

[wantonebad]

Originally Posted by joeychitwood

I bought four and a half acres of pine and spruce trees on a ridge, built a lodge-style house overlooking a river and pond and began a second "career" as a ski patroller in the winter and a mountain bike patroller in the summer at a ski and bike resort. I'm very happy and at peace, but I still dream of looking out over the Caribbean Sea from a porch chair every now and then.

My guess is that feeling gets stronger around end of February beginning of March?

[Blansky]

Originally Posted by wantonebad

My guess is that feeling gets stronger around end of February beginning of March?

My trigger was Halloween. (Growing up in Canada, first snow was right around then)

"Oh god here we go again for another 6 months."

[TheVTCGuy]

If anybody follows this and does buy an island and moves there...

TAKE ME WITH YOU

[wantonebad]

Originally Posted by Blansky

My trigger was Halloween. (Growing up in Canada, first snow was right around then)

"Oh god here we go again for another 6 months."

Not me, I love fall early winter, I think it's my favorite time of the year! It's the end of winter or a winter that hangs on till April that I can't take...

[timedate]

Be careful what you do, i have known people do it and come back missing home and realising that full time residency is much different to going on holiday to a place.

Looking at the rest of europe, and reading about the rest of the world, i have a funny feeling i am best off in the uk, i spent years thinking i want to live in the canaries or spain or portugal, but do i? No, i dont think so, you could end up sitting around drinking with other ex pats, talking about home, as crappy as this country can be at times, i am not seeing anything i think is better, its the same mindset that runs most countries, so you leave one to find it in another, ok the weather is often miserable, but we dont get terrible winters.

I am staying put, i will relocate to the south coast one day, but i think there is life in the old dog yet. Bring on the *rexit.

[BreguetRolex]

I have been going to Sri Lanka since 1975 when I was a marine at the american embassy. Wife and I live in the states from middle of April until early October then 6 1/2 months every year on my most favorite place on earth. I love the heat, humidity, food and people..We will again be leaving early October for Colombo, Sri Lanka.

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[joeychitwood]

Originally Posted by wantonebad

My guess is that feeling gets stronger around end of February beginning of March?

That's spot on. I love scuba diving or reading on a beach for a week or two, but I love the four seasons and winter especially, so I doubt I'll ever become a snowbird.

[JasoninDenver]

My dream would be six months on Maui and six months in Winter Park, Colorado.

We actually bought the mountain house thinking it would be the family home base when the girls have left the nest and the wife retires allowing us to move from Denver.

Problem is in deciding which six months in Maui since we love both summer and winter in the Colorado mountains.

[Mr.Rolex1]

Grass is always greener on the other side...

[GB-man]

Originally Posted by wantonebad

Not me, I love fall early winter, I think it's my favorite time of the year! It's the end of winter or a winter that hangs on till April that I can't take...

Same here. I don’t get tired of winter until well into the new year.

[Blansky]

Originally Posted by JasoninDenver

My dream would be six months on Maui and six months in Winter Park, Colorado.

We actually bought the mountain house thinking it would be the family home base when the girls have left the nest and the wife retires allowing us to move from Denver.

Problem is in deciding which six months in Maui since we love both summer and winter in the Colorado mountains.

I think 6 months and 6 months would be pretty cool although I don't do winter.

I was thinking 6 months Sonoma County and 6 months Hawaii or maybe Australia. Summer and summer.

There is also a misconception that in California we don't have seasons. We actually have 3, just no freezing winter (except in the mountains). We have very nice fall, grape harvest, leaves changing color etc.

[slimboy1974]

Just landed on this thread and absolutely loved it was drawn in from the 1st post delighted you found somewhere your happy with, it was like a book couldn’t wait to read the next post :-)))

[superdog]

Originally Posted by TheVTCGuy

Joey..... Take me with you......

(I speak Spanish, you could use a translator!)

Lmao. You’ve been doing this for 10+ years.

Oy.

[superdog]

Originally Posted by JasoninDenver

My dream would be six months on Maui and six months in Winter Park, Colorado.

We actually bought the mountain house thinking it would be the family home base when the girls have left the nest and the wife retires allowing us to move from Denver.

Problem is in deciding which six months in Maui since we love both summer and winter in the Colorado mountains.

I have a friend that does Aspen and Malibu. She is the EA for a billionaire sales guy.

Not a bad life.

[TheVTCGuy]

Originally Posted by superdog

Lmao. You’ve been doing this for 10+ years.

Oy.

And STILL I can't get anyone to take me

[brandrea]

This is a great thread to revisit.

Joey, I’m SO happy you found peace all this time later after your ordeal. I think Marc’s advice very early on here was very appropriate and it sounds like you followed it.

As for us, we dream about spending part of the year in Italy when we retire. We just love the culture, the language and of course the food.

[Dr.Brian]

I can’t stand the cold, and I don’t mind having only one or two seasons.
I’ve considered going Brando and disappearing to Tahiti.
The problem is travel time to see the kids when they are older and on their own.
Though I could just get a condo/townhouse nearby in the US as well.
I say do it!

[cartesian Product]

Originally Posted by joeychitwood

I was an ER doc for 26 years.

I just joined and came across this thread. Your life has been interesting and I apologize for what brought you here. The fact that you're a member contributing strongly suggests you've adjusted well. Congratulations.

My story is similar to yours, but it happened when I was young, and I have found my new career to be the most rewarding. As the old saying goes, we can't control what hand we're dealt, but we can control how we play it.

[BLACKHORSE 6]

The wife and I have vacationed in Puerto Rico twice and loved it. You get the Caribbean island lifestyle but it’s still the US. We have young children, so this isn’t the right season of life… but someday I might end up as a beach bum on the western end of Puerto Rico in a little town called Rincón.

[77T]

Originally Posted by BLACKHORSE 6

but someday I might end up as a beach bum on the western end of Puerto Rico in a little town called Rincón.

Take Paul VTCguy & TUMI enabler & drone jock. You’ll have a translator plus Anna makes a great beach float…



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