With the type of money that 100 million plus affords most people, it would be enough to live on the water and have a staff which would take care of you forever.
It all comes back to creating a budget.
$2,500 a month for every million you have at a 3% rate (with a planned growth of 5% annually).
100x that is 250 grand a month... before taxes. So, plan on it being more like 150 grand a month. A 10 or 20 million dollar yacht you could live on is still a pretty penny, but isn't unreal if that's one of the main expenditures in your life.
I once went to one of the vacation properties of a billionaire to do some AV work. It was the most unreal property I've ever seen in my life. I think he was worth, about 35 billion or something ridiculous. A bit more than Oprah Winfrey.
Here's a video of the ridiculousness that is the property he used to own...