Here's a checklist of skills that would be good for a bareboat charterer to have. They constitute the curriculum for the US Sailing Bareboat Cruising Certificate. The organization also publishes manuals for these skills.
A list of things that your charter company may or may not provide and which you may wish to bring along anyway.
This company specializes in longer-term and longer-range charters, usually a month or more. Not home-based. Useful for wanna-be liveaboards who would rather try it out before they buy a boat and others who want a month-plus charter but don't want to pay weekly rates.
The ins and outs of choosing a charter company and boat, with a checklist for inspecting the boat.
Some thoughts to help you decide between bareboat or crewed and broker or charter company, as well as how to choose the right boat and check it over when you receive it (including a checklist of gear that should be provided).