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Bareboating is the act of chartering a sailboat that one lives upon, navigates, and operates for a vacation. Common bareboating locations are the Caribbean, the Mediterranean, the Whitsunday Islands, the Ningaloo Reef and other similar warm weather vacation spots.

To charter a sailboat, one must usually be able to demonstrate boat handling skills especially in operating the boat under power, docking, and anchoring. Typical sizes for bareboats come in the range of 30 ft to usually about 60 ft 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. In most traditional charter destinations such as Greece or Croatia the chartering company would ask for a license of skipper in order to charter bareboat yachts.

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