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On my commute home yesterday I encountered a "wide load" convoy that was hauling a millionaire's yacht down the highway. Not a mega-yacht, just a yacht. I don't care that it was just a millionaire's yacht, I felt compelled to roll down the window and give it the bird.
I used to work for a guy who inherited the family company. He used every single loop hole and dirty trick to pay his employees as little as possible, no benefits or insurance... Nothing.
He found out I was turning 40. His advice to me was "a man's age should never be a higher number than the footage of his boat".
He didn't understand that I don't own a boat, didn't own a house, didn't even own my car.
Hell, even if you can afford it, a boat is a bit of a PITA.
Any boat is a PITA, but the longer the boat, the worse it gets. But it doesn't get more 'fun', perhaps even getting less fun. A 20 foot boat with a decent engine can move nice and quick and manuever. Big boat is basically just a less convenient hangout that happens to be on the water.
The only boat fantasy I have is going in a speed boat from Miami to Havana on a whim, mainly because it’s illegal for me to do. And sailing.