A lot of the new sailors I talk to got into sailing so they could charter a sailboat somewhere like the BVI and make their own adventure. There are a lot of tips about this out there, but here are ours.
Planning is key. Planning routes and destinations, then alternate routes and destinations, will give you peace of mind and make your whole experience more enjoyable and less stressful. Do your research on the places you intend to visit and then as many again that you might visit if the weather or mooring/anchorage availability forces you to change your plan. Your research should include things like:
- Currents and tides
- Water temps
- Harbor procedures
- Harbor maps
- Prevailing weather patterns
- Availability of provisions
- Availability fuel
- Pumpout facilities
- Maximum stay length
- Required currency
Charter your boat either directly from an owner or from a company that gets good marks for upkeep. Many charter companies are managing other people’s boats, so that is usually as good as getting a boat directly from an owner. Use a credit card or something like PayPal that will more or less guarantee a purchase like this in case someone pulls a “bait and switch” on the boat you are chartering.
If you are unfamiliar with an area, ask the dockhand something like “is there anything I should know about getting out of here? Any hazards?” This casual question has saved me being beached on more than one occasion. You might also consider having a Captain for a day or two and spending some time talking about the areas you are going after you put him off the boat to get local knowledge.
Check out the boat thoroughly before you start loading in your stuff. You should have a checklist of items like these (this is NOT an exhaustive list!):
- Safety equipment present
- Proper head function and emptied
- Battery function
- Tool Kit on board
- Sails not ripped
- Propane tank adequately filled
- Refrigerator Operation
- Fuel level
- Water Level
My checklist takes me about 45 minutes to run for any boat I’m taking for more than just a day sail. If anything is missing or if there is a problem, don’t be shy about pointing it out to the dockhands.
Before you leave, take the time to stow everything securely. Putting everything away really helps make the boat feel bigger. Use the nooks and crannies and really “move in” to the boat and you’ll find the experience more comfortable.
Desert Wind Sailing 
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