The charter company you choose matters more than most people realize. The same boat can deliver a very different experience depending on how well it is maintained, how responsive the company is when problems arise, and how honest they are about the vessel's condition.
The large charter fleets — companies like The Moorings, Sunsail, and Leopard Catamarans — offer consistency and broad availability. Their boats are generally well-maintained and their processes are professional.
Red flags to watch for: companies that are reluctant to provide references, boats with photos that appear to be several years old, and base rates that seem significantly below market. In charter, as in most things, you generally get what you pay for.