Rhythm & Sails Launches Grateful Dead-Themed Ship Of Fools With Grahame Lesh & Holly Bowling

Rhythm & Sails announced its inaugural Ship Of Fools sailing, a celebration of the Grateful Dead featuring performances on boats and beaches throughout St. Vincent and the Grenadines. Grahame Lesh, Holly Bowling, Anders Beck, Travis Book and Mark Morris will perform during the May 22 – 28, 2027 trip.

Guests will stay aboard crewed catamarans, with four sails lasting between 90 minutes and four hours planned throughout the week. The musicians will play at least one show each day, with impromptu sessions also possible. Between performances, attendees can snorkel, explore the islands and spend time on the beach.

Grahame Lesh, the son of late Grateful Dead bassist Phil Lesh, spent years performing alongside his father in Phil Lesh & Friends and The Terrapin Family Band. Bowling has explored the Dead’s catalog through her solo piano arrangements, including the albums Better Left Unsung and Seeking All That’s Still Unsung. The pianist also performed with Phil Lesh & Friends.

They join three Rhythm & Sails veterans for the Dead-focused voyage. Beck, the Greensky Bluegrass dobro player, serves as the event’s music director. Book plays bass in The Infamous Stringdusters, while guitarist Morris fronts Rapidgrass.

Accommodations include queen cabins with private bathrooms aboard boats staffed by licensed skippers and private chefs. The package includes onboard meals and beverages, daily performances and airport transfers on arrival and departure days.

Ship Of Fools is Rhythm & Sails’ second sailing scheduled for next spring. The previously announced May 1 - 7 voyage features Lindsay Lou, Daniel Donato, Kyle Tuttle and Kellen Asebroek alongside Beck, Book and Morris.

Booking inquiries for Ship Of Fools are open now through the Rhythm & Sails website.