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Even if you have your own sailboat, a good way to learn more about sailing is to charter a boat. Chartering a boat is basically renting it. You can rent all types of boats and yachts that will give you new sailing experiences. You can then add those skills to what you already know about sailing from your own boat. A good way to start is by chartering a boat for a holiday weekend. This will introduce you to a new boat without overwhelming you. There are seemingly endless options advertised on the Internet from Florida sailing charters to Bahamas sailing charters to Caribbean sailing charters. If you book a bareboat sailing charter, you won't have a crew to help you so you should make sure you meet any and all requirements of these private boat charters.
To find the one that's best for you, you can search online under the area you want to sail, such as the British Virgin Islands or you can search under bareboat charters, sailing rentals or sailing charters. Read the details about such a charter carefully. Make sure your sailing resume meets bareboat charter requirements. Most bareboat charter companies will make sure you can provide evidence that the skipper has previous charter experience or owns a similar-sized boat. You might also be asked for evidence that you have at least one experienced crew member.
When you charter bareboat-style, before you leave you should feel confident that you know about the following on the boat you plan to sail: location of safety mechanisms and equipment, safe operation of the winches, reefing lines, anchor(s), VFH system (and mayday instructions), engine operation, halliard's and any systems new to you.