Bareboating
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"Bareboating" is the term used to describe the act of chartering a sailboat that one lives upon, navigates and operates for a vacation. Common "bareboating" locations are the Caribbean, the Mediterranean, and other similar warm weather vacation spots.
To charter a sailboat, one must usually be able to demonstrate boat handling skills especially in operting the boat under power, docking, and anchoring. Typical sizes for bareboats come in the range of 30' to usually about 60' at the upper end. Most charter operators require a sailing resume listing sailing experience, boats that one has sailed and operated, and navigation and racing experience. If the charter operator is not satisfied that one has the appropriate experience, they will often require that the chartering party hire a captain from the charter company to sail with them for a few days.