It would be a water start and finish for the first leg from KW to Islamorada, then a water start from Islamorada. Beaches after that. Most of the logistics are on the RC side (boats, marks, flags, etc.) at each end. I don't think you can count on being on the start boat and beating the fleet to the Islander - we'd need a team at each end. There's only one road and it gets jammed up too easily. Or the RC follows along on the water, but at significant fuel cost.