Founded by Icelantic Ski and travel veterans, the trip spirits a few dozen people to the Caribbean for music and sailing.

And like the rest of the jet set, you’re obsessed. Even though trips like this often start at $14,000 per week per couple (bottomless Champagne and caviar included), there is no shortage of takers.

Garry Hoyt, visionary sailor and advertising executive, passed away peacefully at home in Newport, Rhode Island on March 31, ...