I've been retired exactly for 1 year and 2 days now.
Where?
Part-time in Barbados (~4 to 6 months in total but intermittently, not continuously)
Why?
Positives (immigration process, tax's, health care, COL, diversity, acceptance of foreigners?)?
My husband was born in Barbados, but raised in the US.
Built-In family is wonderful! It's so comfortable laughing and joking with them. Hearing stories about all the different family members and especially stories about my husband when he was a kid are priceless and great blackmail material (hehehehe).
Bulit-In friends (great resources especially since it's a very small country (a little under 300K).
Immigration - the process took little over a year, but would have been shorter if we didn't have a pandemic. It was relatively easy paper work. Communication was great, since the country is so small, everyone knows everyone and they know how to find you if they need you (hehehehe). I don't quite remember how much, but at least $800.00 US and I had to be "related" to Barbadian (my husband).
Taxes - hmm, not sure, can't comment yet.
In 2018, we purchased and renovated a property that we turned into a multi-unit across the street from a great beach on the Caribbean side. We currently rent out the top and back units for short-term rentals and the business has been picking up lately.
Healthcare is dismal there- most people who stay for an extended period of time get healthcare in their "home" countries like Canada, the US & the UK mostly.
Diversity - the vast majority of Barbadians are of African Descent. They are some of the WARMEST people I have ever encountered. They are very helpful but also chatty and gossip-y, which I guess speaks to how small the country is. They are extremely polite to visitors and to each other too. My theory is that since it's such a small country, you are bound to interact with one another or some how related to one another, therefore they keep it super polite. I really like this about their society, people have decorum and manners.
What I also enjoy about the Island is that we live in a vacation place where there are many different people in my neighborhood. For example, the house to my right is a native Barbadian who's family has been in that house for over 200 years, behind me is a cousin of his who lives in the UK, on the left of me and behind are short term rentals and then Sweedish people behind them. I like that there are lots of activities to participate in when you feel the urge to party, but also the "sleepy beach" aspect is a welcomed feature I also enjoy. I love the peace and calm that my early dawn beach walks bring to me any time I want.
Negatives (immigration process, tax's, health care, COL, diversity, acceptance of foreigners)?
Expensive/Lack of choices - food, transportation, etc. The grocery store prices are comparable to California which ain't cheap. Also, the different choices are not so great especially the vegetables. In my opinion, they eat a very limited variety of vegetables, so that took some getting used to. They drive on the opposite of the road for me, so I didn't drive there for a while, but now I feel comfortable driving. Car insurance is very expensive and used cars are relatively expensive, forget about owning a new car, it would be like a small mortgage (mostly due to import taxes).
Slow-motion - everything is on slow-mo. Standing in line. Waiting for government documents. The slowest by far was the real-estate process. We had to get a lawyer, luckily my husband's family had a family friend who happens to be a retired Supreme Court Justice (hahaha, yup - my lawyer was a retired supreme court justice - that's how small the country is hehehehe). In the US closing takes about 1 month, two months at the longest. Not in Barbados! It took almost 9 months! Ridiculous I tell you! Renovations - again a little lucky here because we used an established contractor on the Island who happens to be my husband's first cousin- so we trusted him and he is very experienced, but it still took what seemed like for-evvvvvvveeerrrrr! This was NOT our first rodeo as we have flipped houses in the past and are land-lords. But golly - what would have taken us about 3 months in the States took about 1 year in Barbados! However, I really can't complain because the work was spectacular! They take pride in their craftsmanship and they are really talented, polite and want to do a good job for you. So in the end - working with family and the varied artisans was actually a great experience and we all became closer as a family.
The final benefit that is very important to me is that we don't lack visitors because everyone wants to come visit a tropical island (hehehehe). I've really enjoyed hosting friends and family. Reconnecting with them on "slow-mode" has been absolutely wonderful and memorable. But when they leave, I get a nice little break, so best of both worlds!
Overall, I absolutely love spending my life part-time in Barbados.