Why the format and the place fit
Almost nothing in Key West is a ballroom. The venues are historic properties with small rooms, open terraces, private homes and boats — and every one of them defeats a performance that needs a stage, a sound system, a power supply and a sightline.
Close-up magic needs none of them. On a moving boat it is effectively the only workable format, because there is nowhere to put anything and nothing stays where it is put.
The guest counts are small, typically thirty to eighty, which is the scale at which this format is strongest rather than weakest. Everyone is reached properly, with time for guests' own objects and the evening's own details worked into the material.
The calendar here is genuinely seasonal and weather-shaped. Dates are worth checking early not as a sales line but because the island's inventory of suitable evenings is small.