About a year or so before I reached 60 (I'm 74 now) I started one investment club and joined another with a view to building up a pot of money so that when I retired (my OH was self employed) we could go on a coach trip around the eastern Med. There was a specialist company that took small parties in Mercedes buses on various journeys in Europe, N Africa, the Silk Route and so on. I wanted to see Leptis Magna, Craque Chevalier and so on. However, the war in Libya put an end to that idea. We wanted this holiday before we decided what we would do in retirement. The clubs broke even so not a lot of money involved. and I acquired a new puppy instead.
I'd always wanted a house in France for holidays which my OH was against because he didn't want to spend his holidays doing up houses as he'd had enough of doing that in England. So we decided to retire here. When my FIL died we used my OH's inheritance to pay off some debts and buy a plot of land to build a house. Which we did. I have a slight regret that we didn't do it 10 years earlier.
We have had very few long haul holidays until we were in our late 50's and most of our holidays were spent in France or Italy. Luckily we both like the same sort of thing.
One thing that I would say is that it's important to have some pleasure in your life all the time. I made a New Year Resolution when I was 40 to make sure that we did something really enjoyable every month. We like the arts and aren't interested in sports so we went regularly to London, Norwich, Cambridge and Ipswich, plus Snape Maltings and a few other places to see ballet, cinema concerts and exhbitions. Our finances have been up and down - when they were up I got seats in the Grand Tier at Covent Garden. When they were down we had standing tickets behind the stalls. Substantially cheaper than the stalls seats in front of us.