The granddaddy of cruises on this list, Blues Cruise was founded in 2002, and sells out both of its twice annual sailings well in advance. In fact, its upcoming sailings are already wait-listing people. Why is this such a hot ticket? In part due to the jam sessions and artist workshops that make it much more interactive than the typical concert setting. A lot of blues fans are also amateur musicians — and the opportunity for them to pick up an instrument and jam alongside their idols makes this the highlight of a lifetime.