I decided not to wait until retirement to start long term traveling - my work allows it. Not doing anything super long term, two months max in one place.
An advantage to doing it now is my health is good.
I buy travel insurance for long periods (good up to 6 months). It has medical coverage (primary) and evacuation, plus the typical travel stuff.
Yes, quality of healthcare is very uneven in many countries, including the U.S. but if you live there you know where to go.
My friend’s daughter went to Guatemala for a surgery - not because of cost, but because Kaiser doctors here told her they needed to remove her ovaries (for benign tumors), and she was in her early 20s. In Guatemala she had a relative who was a VIP in a good private hospital. She had the surgery there, kept her ovaries, and went on to have three kids.
While I might like to be elsewhere, I will probably relocate to wherever my kids settle to support them. I never had any family support in raising my own kids, and I know how much I missed. I will gift that to my own kids if they want it as adults.
@Consolation Toronto’s better! 
Come for a visit and I’ll show you around.
It’s been my plan to spend the six colder months in either Mexico or USVI. My recent divorce postponed that for the time being, but I’m now again on the five year plan to do it solo. First step is completing my in-law apartment and I’m happy to say the foundation has been poured and the lumber was delivered yesterday…baby steps. Financially I need to rent my house to do this, thus the in-law for myself. Top of my list is Isla Mujeres and St. John. I’m also on a board for singles moving to Mexico and I’m reading about some amazing spots with active expat communities. St. John can be very expensive but they are currently rebuilding and work seems abundant, that probably won’t be the case in five years though. If Mexico, I’ll hopefully find remote work. In St. John or other USVI I’d most likely work in hospitality.
I want to be a NS flight from Boston, within 4-5 hours tops so that the travel isn’t too restrictive, both cost and time-wise. I’ve had medical care in Mexico and was very pleased and of course USVI will accept the same insurance as the states.
I just saw an FB ad for a nonprofit that runs schools in Antigua, Guatemala. Volunteers come to help the teaching staff teach English, etc for a minimum of 4 weeks. DH and I are interested in something like that. Dh would be able to practice his Spanish, too.
@NEPatsGirl are you at all concerned about safety in Mexico? I have read a lot recently about the danger there but I’m curious if you feel it’s true only in certain areas.
@rom828, violence is becoming more prevalent all over the yucatan but is not nearly what you find in the major Mexican cities. Isla is pretty remote in that it is so small, 5m x 1/2 m, and requires a ferry over from the mainland. The cartel isn’t especially interested in areas like that. There is some increase in petty crime on Isla but a clear head can avoid that stuff.
^You plan to lease it in summer and live there in winter? Winter there is not very nice, cold and wet.
@martharap I also have a son who lives in Sydney (over 2 years now) and therefore I am always checking out Australia. Like you, my plans depend on where the kids settle.
My thought is to divide my time between US, Penang and India. Still in nascent stages of planning.
Forget New Zealand if you want to buy a home. That country just banned real estate purchases by foreigners.
I have a cousin who moved to New Zealand. The only way he could do it was to buy a business and make it profitable for a couple of years.
Crossed the first hurdle towards getting dual citizenship with Italy. I hope I clear the rest of them! Retirement and moving around will be much easier that way.
^How exciting, @greenwitch. How long of a process is it? Why Italy?
Here’s one who did not wait for retirement to move! Summer Sanders. Moved to NZ and no regrets.
I can easily get German citizenship…by presenting my dad’s birth certificate, his immigration into this country papers, and my birth certificate. He was stateless after WW 2, and was not offered citizenship anywhere. Because of this…he and his bloodline heirs can claim German citizenship.
I just need to gather these things up…and head to a German consulate.
Believe me…it’s a thought.
@lilmom - it’s the only country of my ancestry where it is even possible, given my particulars.
And then I can sponsor my H and all the kids. Chain migration, lol. I think it’s just a good thing to have. To have options, easier travel, etc.
@greenwitch I agree, and that is why I am considering dual citizenship as well.
And in my case…no hoops to jump through.
I hope not! But if you have to deal with certain states (cough, NY, NJ, cough), there will be hoops. And you probably need to get all your US documents translated into German. Good luck!