I'm sorry to say that you are not going to have any luck organizing an event like this. The only people interested in the event would be the top two or three teams that might actually win the event. The rest of the teams would not be interested in making donations to the top team.

The only way an event like this could work is if a sponsor were to provide the prize money. Then the entrance fees would be reasonable and people would be interested in entering to win the sponsors money.

Mike Worrell had been running the race for more than 20 years prior to his attempt to change his event. Worrell no longer participated in the race. While he was charging 5K he was planning on providing about 5K worth of value to each entrant.

This is totally different from what you are planning. I'm afraid to tell you that you won't be getting any interest from the sailors with the event you are planning.