Article Contributed by Gratefulweb
Published on 2026-10-29
DENVER, Colo. — Rhythm & Sails, the boutique charter company pairing crewed catamaran sailing with intimate live music in St. Vincent & the Grenadines, will set sail twice next spring. Over the past few years, guest demand has outpaced cabin count aboard the catamarans and Ship of Fools arrives to accommodate fans with a finger in the air.
"The easy move was to add more boats to our trip in early May but we didn't want to do that," said founder Ashley Hart, who has sailed these waters for more than 30 years. "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."
The Ship of Fools lineup was curated around musicians who carry the Dead's songbook and culture as their own:
“To say I’m excited is an understatement,” said Music Director Anders Beck. “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.”
The artists will be on board for the duration of the voyage, playing unique shows on and off the catamarans, in beautiful locations throughout the island chain. But guests will quickly realize that music is just one piece of an entire experience that Outside named one of the “Top 10 Tropical Adventures in the World.”
“It's the coolest trip I’ve ever been on," said Holly Bowling. "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!"
Each boat sails with its own captain, first mate and private chef to take care of guests throughout the week. Days are spent snorkeling vibrant reefs or diving to shipwrecks; relaxing on quiet beaches or exploring the islands, all while enjoying freshly prepared meals and an open bar on board. Evenings bring intimate performances and spontaneous collaborations that simply can’t be replicated in traditional venues.
Ship of Fools departs from and returns to the main island of St. Vincent, following a similar route to the May 1–7, 2027 trip. But no two Rhythm & Sails trips are ever the same, guaranteed.
Limited cabins are on sale now at rhythmandsails.com/ship-of-fools. The trip cost is $8,970 per person (double occupancy) and guests can reserve their spot for a $975 deposit, with payment plans available.
Rhythm & Sails is a boutique charter company offering unparalleled experiences for discerning music fans. The company specializes in exclusive experiences that blend luxury sailing, Caribbean exploration and intimate live performances you can’t find anywhere else. Additionally, Rhythm & Sails’ private charters offer guests the opportunity to live their dream on a fully customized journey tailored to their exact specifications.
SHIP OF FOOLS: RHYTHM & SAILS
May 22–28, 2027
St. Vincent & the Grenadines
Featuring Grahame Lesh, Holly Bowling, Anders Beck, Travis Book and Mark Morris
$8,970 per person (double occupancy)
$975 deposit | Payment plans available
Reservations & More Information
