Help others enjoy boating
Okay, you successful business men and women who are entering retirement lets make a deal. Many of us can't afford a sailboat let alone charter one for a week yet we love to sail. Sailing interests have dropped. Many kids are not introduced to sailing and never have the opportunity to get involved.
When I was in college several times during the summer, I would get im my car early in the morning and travel to the eastern shore arriving at a marina, find a boat that the owner was working on and picked up a conversation. Soon I was sanding and painting the bottoms of many boats, finishing the teak and cleaning the cabins. For this, I not only found new friends but they were nice enough to invite me on weekend sailing cruises.
It would be great to promote these opportunities almost like match.com. The benefit to a boat owner, well they get help on the many different maintenance tasks and the boatless person they get to sail. The tirhg mix of personalities is required but I never had the problem.