The compelling part of this game is the ability to bet on or invest in other players gamepieces. At the start of play, (lets say 4 players and 4 boats) each player has an initial amount to invest (their own colored tokens) and they do so by passing around a little vault (with 4 slotted compartments and a little privacy shield) and distributing their tokens into those compartments how they please. The compartments correspond to gamepieces. As play progresses, they invest a token each turn (or more, if they get rewards from gameplay) so that as the game evolves and the probable outcome becomes more or less apparent, they can invest differently.
The hard part...you need a sort of game now where people can pursue a turn by turn "ulterior" motive ( gathering treasure from little islands?) without revealing too much of their overall goal, which is to have the boat they invested in most heaviliy win. That is the winning condition - play continues until only one boat is left, and then the vault is opened. The player with the most tokens in the vault of the winning boat, wins the game. I came up with a card based movement system in which the cards can move all the boats a few (2 or 3?) spaces in one direction or their own boats more (5 or 6?) spaces in that direction across a grid. You can combine cards during your turn, so you might move all boats North 2 spaces and your own boat West 5 spaces to land on an island containing treasure which you can then invest. But you also moved all the boats North, perhaps because you want to sink a boat near the Northern edge of the board - boats are destroyed when they fall off the edge of the board. Or you may have done so to move the boat near the Southern edge further to safety. So, you need a game where there are numerous possible motives behind every action.
This is one idea I had, but I don't much like the way it plays. There is something interesting about moving all the pieces at once ( perhaps the players represent the four winds and have wagered on the success or failure of four merchants and the boats are getting blown around...) but I made a mock-up and I couldn't feel much real strategy there. Anyway, I'm only describing it so you can understand how the betting system might work.
My real question is, can you think of games where the winning condition works this way? You can invest in the success of another player's piece - in fact the pieces only ostensibly belong to the players- and only at the end of play is it apparent who invested most wisely?
Do any of those games have a winning condition related to bets/investment?