Three things... I am on the cusp of retirement so this topic is near and dear to my heart..
(1) My second wife (and I am in Canada, which is likely relevant) is a school Principal. With an awesome pension. You may want to reconsider your choice of spouse. Screw love, marry for money.
(2) The people who told you to start saving decades ago, weren't wrong. You should have listened. My pension earned three times what my job paid last year. It's like having a tribe of peons shovelling money into my bank account, so yay me.
(3) The serious one... Mrs. Stoo and I talk about this a LOT. Retiring in a place where we can dive our faces off every day, mostly requires "cohones". You just have to do your research and then "do it"...
A few years ago, my son was travelling and ended up in Bali. He doesn't dive, but he emailed and he said "Dad, you would LOVE it here... amazing diving, fantastic food, friendly people... and dirt cheap". So that got me Googling...
I came across a blog, kept by a couple from the Chicago area. Their life seemed similar to mine... solidly middle class, a house, a cottage, some pension etc. They had gone to Bali on vacation and loved the place. Like all of us, they decided that they would move there one day. Only they meant it...
So in a nutshell, they sold their cottage and put their house up for rent. They took the cottage money and bought a small tract of waterfront property in Bali, hired some locals and built a modest home, and three even more modest guest homes that they intended to rent. Because they were going to be operating a business, and hiring some locals to work there, they easily qualified for residency.
They moved there and their little business provided enough income that they didn't need to tap into savings. They dove often and made lots of "local" dive trips to the places we North Americans dream of.
They intended to stay there as long as (a) it was still fun, (b) they didn't require significant health care. When they were ready to come back, they'd simply email the tenants in their home and then move back. They'd simply pick up where they left off.
That was maybe three years ago I read that. Since then, I have tried to find the flaw in the plan, and I haven't found it yet.
See... just balls to do it, and some careful planning.