Jam band stars highlight luxury catamaran cruises for Colorado company

Stepping on board a Rhythm and Sails 50-foot catamaran with 35 people and a guest performer makes even the smallest music festivals look like Coachella by comparison.

That’s because concert fans, who have for decades trekked to massive destination events such as Bonnaroo, South By Southwest and Coachella — returning to California this weekend with an expected 125,000 daily attendees — are increasingly hungry for something more intimate and curated, said Rhythm and Sails founder and “admiral” Ashley Hart.

“In a group setting, it might normally take a few days for folks to get into their groove,” said Hart, who is also a sales manager for Golden’s Icelantic Skis. But after the first night on board a Rhythm and Sails cruise, “everybody’s flourishing … by night two, everybody’s on the same wavelength.”

The Colorado-based company’s week-long experience — which typically takes place around the Caribbean island of St. Vincent and the Grenadines — hums with acoustic guitars, multi-part harmonies and unexpected moments of connection in a gorgeous tropical setting, he said.

Some of the musical guests this spring will include national names such as Anders Beck of Greensky Bluegrass and Travis Book of The Infamous Stringdusters. Others, like Eddie Roberts and Torrin Daniels, are Denver-based, while Mark Morris (of Rapidgrass) is in Silver Plume. The acoustic, bluegrass and jam-band musicians have known and played with one another for years at Colorado-based shows.

The experience is one of the latest and most upscale versions of gig-tripping, a hot travel trend that finds music fans ponying up thousands of dollars to see their favorite artists in offshore settings. Part of the reason for the trend is that as demand and ticket revenues have increased steadily since 2021, an increasing number of concertgoers are looking for something unusual, explained Damian Quigley, Rhythm and Sails co-founder.

“You don’t have to sneak backstage to chat with the artists,” said Quigley, an adventure-travel veteran who runs the snow sports-focused Storm Mountain Media. “It’s more about these little organic moments that you don’t see coming, like a musician floating around the back of your catamaran in a dinghy and playing a song before you go to bed.”

Roughly 60% of Americans are open to flying internationally “if it means scoring cheaper tickets to see their musical heroes,” according to a survey from travel insurance company Generali Global Assistance. This developed in part because of Taylor Swift’s Eras Tour, where exorbitant U.S. ticket prices and instant sell-outs prompted some fans to fly overseas for better access, Generali reported.

But if you’ve got the disposable income, why not let someone else — or, in this case, a team of chefs, boat captains, floating bartenders and bluegrass pickers — sweat the details?

“It’s about the little surprises throughout,” said Greensky Bluegrass‘s Beck, who also serves as the music director, booking the live acts for Rhythm and Sails. “This isn’t for everyone, so I pick musicians that I think will thrive in the format, including people who are really excited about interacting with guests for a week.”

Other musical guests will include acclaimed pianist Holly Bowling (Ghost Light, Phil Lesh), Jay Cobb Anderson (Fruition) and Megan Letts (Mama Magnolia).

Even though packages start at an eye-watering $7,970 per person, Rhythm and Sails is in line with (if not cheaper than) most all-inclusive packages for upscale adventure travelers, according to a Denver Post review. And its trips have been selling out for the past four years.

Sample activities on shore might include relaxing on a beach, golfing and small concerts, while boat activities include fishing, snorkeling and on-board charcuterie picnics.

Hart said that the last decade has seen a sharp rise in similarly curated events. Think European waterways — replete with wine pairings — and boutique trips geared toward personal tastes, such as Saratoga, Wyoming’s Brush Creek Ranch. There you can select from all-inclusive options such as fly fishing and hunting packages, culinary education, and even reserve your own ski mountain for yourself and 18 guests (for $8,500 per day for 600 acres of trails).”

Setting the tone on the first day of a small-group vacation is key, Quigley said, and something he’s learned how to do over decades of booking shows and leading adventure-travel trips.

“We ask people who need to use their cellphones to step away for a minute, unless they’re taking photos or playing music,” he said. “As a result, we see people come out their shells more quickly.”

Trading the ski slopes for white-sand beaches and crystal waters is not a new dynamic for Colorado travelers. Unlike Coachella, Rhythm and Sails doesn’t typically attract 20-something influencers chasing TikTok clout. In fact, about half of them at any time are young-to-middle-aged bluegrass, folk and jam-band fans from Colorado, Hart said.

“It is expensive, I’ll say that,” said Hart, who declined to share Rhythm and Sails’ revenue or budget. “But we are not in this business to be making a boatload of money. We’re trying to keep this authentic and be our true selves. This is a life-changing thing where you make 30 new best friends every year. I’ve also been going down there for 30 years and captaining boats myself, so we’ve made it the smoothest experience possible.”