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The federal government issues licenses, and the ASA, a private corporation, issues certificates. An ASA certificate is not necessary for any purpose, but it can help you prove to a boat charter company that you are competent to rent a yacht. Generally, you don't need either a license or an ASA certificate to operate a recreational boat, regardless of whether you own it or are renting it, and regardless of whether you're sailing across a small inland lake or around the world. If, however, you operate a boat for commercial purposes, or if you carry passengers for hire, you need a license from the government.
Most 27 foot sailboats wouldn't be up to the kind of cruise you're contemplating, but some of them would be. It depends on the design and construction of the boat. Two people would be able to do the trip. Actually, only one person is necessary to sail the boat, but you really should have someone else to stand watch while the other is sleeping.
Last edited by Sailormon6; 03-07-2006 at 08:07 PM.