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Ship of Fools: Rhythm & Sails’ Grateful Dead Voyage Will Feature Grahame Lesh, Holly Bowling, Anders Beck and Travis Book

11:52 AM EDT on October 29, 2026

Rhythm & Sails, the charter company that offers intimate experiences with crewed catamaran sailing and live music has confirmed that it will offer two voyages in 2027. Both of these will depart St. Vincent in May and offer a special Grateful Dead theme. Ship of Fools: Rhythm & Sails’ Grateful Dead Voyage will feature music from Grahame Lesh, Holly Bowling, Anders Beck, Travis Book and Mark Morris. The initial journey was set for May 1-7 and the second one has been added for May 22-28.

Rhythm & Sails founder Ashley Hart notes, “The easy move was to add more boats to our trip in early May but we didn't want to do that. The small group size is what makes our trips so special. You get to know everybody by the second night and the artists are right there with you the whole time. A second week allows us to share that with more people without diluting the experience.”

Anders Beck, who serves as Music Director, adds, “To say I’m excited is an understatement. I pride myself on assembling unique groups of musicians who can create a once-in-a-lifetime experience for our guests. The ocean is a powerful place and I really think that taking this music we hold so dearly and putting it in another geographical context, and really spiritual context, is going to blow a lot of minds.”

Holly Bowling adds her own testimonial: “It's the coolest trip I’ve ever been on. I’ve traveled a bunch but never to places like this. It's not like a festival where everyone’s scattered in different places. We’re basically a family for a week, in this insanely beautiful corner of the world. Show me a better day than waking up and throwing myself off a sailboat into the ocean, playing music with a bunch of my friends, and ending up back in the ocean under the stars. I mean, come on!"

All of musicians are on board through the journey, performing music on and off the catamarans in locations throughout the Grenadines. Each boat has its own captain, first mate and chef. In 2024, Beck spoke with Relix about the Rhythm & Sails experience.

A limited number of cabins are available, with additional info at rhythmandsails.com/ship-of-fools.