Hiring someone to sail your yacht or sailboat can be a stressful decision. There are many considerations to think about. How experienced are they? Have they sailed a boat similar to mine? Will they be professional and maintain the boat on the water? How much is too much for sailboat delivery captain rates? As with anything, price dictates value. If you are going to find the cheapest captain out there, you will probably end up the cheapest level of service. Below are a few things to keep in mind when negotiating pricing with a sailboat delivery captain: