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Step 1
Decide on the time of year you want to travel. Summer and autumn are hurricane season in the Caribbean, and not an ideal time to charter a boat there.
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Step 2
Decide who you are traveling with. The number of people who charter a boat can significantly decrease the overall cost and it affects the size and type of boat you can consider.
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Step 3
Decide which type of boat you are interested in: sail or powered yacht. Research the different models of boat. You will need a working knowledge of the different models of boats to save you from many headaches later on. This helps with gaging the quality of the boats offered, once you contact charting companies.
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Step 4
Decide if you will go bareboat (without a crew) or crew and if you need a full crew or simply a captain. If no one in your party has ever sailed before, or even if they have, but aren’t very experienced, most definitely hire a crew. Be honest with your skill level when charting a boat.
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Step 5
Decide if you want full-service (meals provided) or if you will provide the food yourself. If you provide food for yourself, you will need to map out locations along the way to make port and pick up provisions.
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Step 6
Contact and interview charter companies and potential crews. Make sure to get a detailed description of the boat. Most importantly, ask the condition it is in, its age, how long it has been in service. Get everything in writing. Feel free to ask them to send pictures of the actual boat.
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Step 7
When paying the deposit, make sure your deposit is held in a true escrow account until just before departure. This way, if there is a problem, you have a valid means of recourse.
