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Joe from Boston
Old 05-16-2019, 05:34 AM   #1
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Joe from Boston

Hi. I live in Boston and am getting sick of the weather. My first son is off to college this year and I have two more that will be gone in the next 4 years. I am starting to think about retiring someplace warm. My wife likes Charleston and Savannah, but I would prefer something further south, possibly the Caribbean (St. Martin) or Central America. In the menatime, we are having fun visiting these places and doing our due diligence.

I have a small online business so could continue working from anywhere!
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Old 05-16-2019, 05:42 AM   #2
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Welcome here JoefromBoston!!!

Happy wife, Happy life....

Don't forget the important things.

Best wishes for your move to an area that makes
you both happy.

VW
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Old 05-16-2019, 07:07 AM   #3
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Hi. I live in Boston and am getting sick of the weather.
Welcome. From the same area. I had already decided to move south, and this past winter confirmed my decision. Still wearing a coat every morning.
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Old 05-16-2019, 07:30 AM   #4
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Welcome Joe.
How about Florida as a compromise? If you go further south than Orlando, there is no real winter to speak of except perhaps 3-5 days with highs of 50's in January.
Be sure to check out how one would live as an expat vs. as a visitor. Could be reasonably different than what you might be accustomed to.
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Old 05-16-2019, 07:36 AM   #5
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If you're interested in the coastal South, Beaufort, SC is a lovely city that's cheaper and many think more livable than Savannah or Charleston.

If you're wanting the warm winters, you have to move south of Orlando.
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Old 05-22-2019, 02:58 AM   #6
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Please visit the Lowcountry (what we call the lower coastal areas of SC) in the summer before you make up your mind. It is very hot and humid!
Beaufort is a fairly sleepy town, but nice for those who enjoy getting out on the water. Not as much in the way of cultural offerings as Charleston or Savannah, if that’s your thing.
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Old 05-22-2019, 03:31 AM   #7
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Originally Posted by JoeFromBoston View Post
Hi. I live in Boston and am getting sick of the weather. My first son is off to college this year and I have two more that will be gone in the next 4 years. I am starting to think about retiring someplace warm. My wife likes Charleston and Savannah, but I would prefer something further south, possibly the Caribbean (St. Martin) or Central America. In the menatime, we are having fun visiting these places and doing our due diligence.

I have a small online business so could continue working from anywhere!
My brother wanted to move to Panama after retirement. I never heard my SIl say that, but after the first grand kid came last year, they bought a year round lake house within 45 minutes of that daughter. They too still go to warm places, but want to be nearby to see the grandchild.
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Old 05-22-2019, 04:29 AM   #8
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Welcome Joe.
How about Florida as a compromise? If you go further south than Orlando, there is no real winter to speak of except perhaps 3-5 days with highs of 50's in January.
Heck, half of Boston lives in Naples in the winter! You'll meet all your old friends.
We're on the other coast (Fort Lauderdale) and we hear you on the winter thing and some days it can be like living in a foreign country without going through customs!

Wherever you decide, my suggestion would be to keep a foot in each place for a year or two; don't burn any bridges immediately. Living someplace is very different that spending a few weeks.
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Old 05-22-2019, 04:55 AM   #9
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We were tempted to move to the Keys at one point in our journey.

We rented a nice house in Marathon for a month to test the proposition. It took about two weeks for the vacation vibe to evaporate. The next 14 days showed us what it would be like to actually live there full-time. Still love the Keys as a vaca spot, but learning the downsides talked us out of moving there. An extended stay can be an eye-opener....
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Old 05-22-2019, 05:11 AM   #10
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Originally Posted by JoeFromBoston View Post
Hi. I live in Boston and am getting sick of the weather. My first son is off to college this year and I have two more that will be gone in the next 4 years. I am starting to think about retiring someplace warm. My wife likes Charleston and Savannah, but I would prefer something further south, possibly the Caribbean (St. Martin) or Central America. In the menatime, we are having fun visiting these places and doing our due diligence.

I have a small online business so could continue working from anywhere!
Rent in the area that interests you first.

"Someplace warm" can be appealing to a New Englander after a cold winter and wet/cool spring. But "someplace warm" can turn into "oppressively hot" in other seasons.

Unless you are talking about something like Aruba where there are no different seasons...
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Old 05-22-2019, 05:11 AM   #11
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They too still go to warm places, but want to be nearby to see the grandchild.
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Wherever you decide, my suggestion would be to keep a foot in each place for a year or two; don't burn any bridges immediately. Living someplace is very different that spending a few weeks.
I enjoy, believe it or not, living in my part of New Jersey. Both of my kids, and their combined 4 children, live very close by. If I didn't have them nearby I would have relocated south. Seeing my grandkids as often as we do is priceless. OP, your kids are young. I suggest you hold off any permanent relocation until you see your kids settled. Skype is a substitute, but at least for me would not be enough.
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Old 05-22-2019, 02:03 PM   #12
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I am starting to think about retiring someplace warm.
I can relate. My original "retirement plan" was to put the snow blower in the back of the pickup truck and drive south until people started asking what that machine was for.

Alas, DW didn't want to move that far from family, so here we are in WV.

On the bright side, I have found that enduring winter while working and having to go outside every day is very different from retirement when one has the option of saying "Nope, I'm not going outside today". The latter is a lot better.
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Old 05-22-2019, 03:18 PM   #13
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Welcome Joe !

I also left Boston in 1997 and visit every other summer or so. For me, the warmth (heat) compensates for all the wonderful things that Boston has to offer. It's just better to live in a place that has a heat index rather than a wind chill factor

Rich
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Old 05-30-2019, 06:12 AM   #14
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Thanks for the warm welcome and helpful advice!
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