Music has an intrinsic power to transform people, places and moments. To unite, to heal, to create joy and memories that will last a lifetime. For these reasons, live music is central to the Rhythm & Sails experience and each trip will feature a unique combination of our favorite artists.

When you combine an incredible amount of talent, a purely inspirational atmosphere and genuine group of people, it creates an organic musical experience that you simply cannot find anywhere else. Throughout each trip, you’ll be treated to daily, one-of-a-kind shows that you’ll never forget. 


Paul Hoffman

Greensky Bluegrass

Paul Hoffman, like his band Greensky Bluegrass, is all about duality. He is a rockstar of a frontman, yet subtle in his poetry. The depth of his lyrics make think about what he’s saying…

and feel the emotion throughout, while his playing leaves you no choice but to dance your ass off. In addition, his unassuming nature makes it somehow hard to believe that so many people would call him their favorite songwriter in the world. Having grown up on the shores of Michigan, Paul is a lover of aquatic adventuring, does a great impression of a breaching whale and jumped at the chance to join the Rhythm & Sails roster.

Anders Beck

Greensky Bluegrass

Anders Beck is the wickedly talented dobro and resophonic guitar player for the progressive band, Greensky Bluegrass. His unique style and use of different tones and effects…
have put him in a category all his own throughout the world of bluegrass and jam bands, helping propel him and Greensky to the forefront of their genre. Through his innovative style of playing, he has the uncanny ability to elicit deep emotion from listeners as he explores the possibilities of the improvisational spectrum, while also subtly supporting the musicians he shares stages with. Throughout any performance, his charisma and sense of humor will ensure you enjoy the show without taking anything too seriously.   

Travis Book

The Infamous Stringdusters

It’s hard to pin Travis Book down. As bass player for The Infamous Stringdusters he’s a Grammy-winner (and 4-time nominee) who’s played over 1500 shows in 17 years. 

As host of a weekly gig in his hometown of Brevard, NC, he fronts an original rock band, a country band, a jazz trio, an old time trio, a bluegrass band, a swing band and a Tony Rice Tribute, as well as backing Americana legends like Tim O’Brien and Jim Lauderdale. Upbeat, positive, optimistic, inspired, not one to sit still, in 2023 you’ll find him heliskiing as part of Heligrass and serenading guests on the high seas at Rhythm & Sails. If there are good times to be had and music to be made you’ll probably find him nearby, singing, laughing, and generally looking on the bright side.

Jay Cobb Anderson


Jay Cobb Anderson knows that music magnifies the human condition, highlighting both daily struggles and personal triumphs with the same sensitivity and sympathy… 

The Seattle-based singer, songwriter, and multi-instrumentalist accepts the responsibility of such sonic discourse via his solo output. Moreover, he deciphers these universal experiences in the form of hummable, hypnotic, and heartfelt anthems steeped in storytelling folk tradition and amplified by unabashed rock ‘n’ roll energy. You can catch Anderson on the road solo, or with his other nationally touring bands Fruition and TK & The Holy Know-Nothings.

Lindsay Lou

With a voice that will stop you dead in your tracks and an impressive instrumental prowess to boot, it’s no wonder that Lindsay Lou’s star has been rising steadily over the past decade. 

A soulful singer, songwriter and musician, Lou grew up surrounded by music and felt it only natural to pursue it as her life’s work, eventually moving from Michigan down to Nashville, Tennessee. While she’s played in a number of groups, she’s also released a host of solo albums that showcase a mastery of various styles and sounds that keep the listeners guessing. Throughout the year you can catch her gracing the stages of venues and festivals far and wide, sitting in with notable names like Greensky Bluegrass, Billy Strings and more along the way.

Kyle Tuttle

Kyle Tuttle Band

Kyle Tuttle spent his teenage years shredding the guitar in punk rock bands and hasn’t lost an ounce of that electric energy as his musical style has evolved over the years. 

With his focus now on the banjo, Tuttle has developed an absolute mastery of his craft, capturing the title of National Banjo Champion along the way. He spent three years as an integral part of the Jeff Austin band and is now a mainstay with Molly Tuttle & the Golden Highway as they tour the country. Outside of these groups you can catch him as an artist-at-large at events across the country, thanks to an infectious spirit and positivity that make him the perfect complement to any setting, musical or not.

Mark Morris


Mark Morris began playing guitar when he was just 10 years old. He later earned a Music Business degree from the University of Colorado and has been a professional touring musician…

promoter and teacher for almost two decades now. He founded the band Rapidgrass in 2012, along with multiple music festivals, and his music has taken him across the world, throughout the US, Canada, Europe, Asia, and Central America. When Mark is not performing, he works full time as a music promoter and talent buyer for multiple festivals and events. He’s also served as the US ambassador of bluegrass at La Roche Bluegrass festival since 2016 and has shared jams and stages with Dierks Bentley, Sam Bush, Edgar Meyer, David Grisman, Peter Rowan and many others.

Charlie Rose

Elephant Revival

Charlie Rose began a life of music at a young age playing piano, guitar, trombone, and singing. In college he found additional room for the banjo, mandolin, and upright bass.

Among the many amazing musicians he encountered in those formative years were Bonnie Pain, Bridget Law, and Dango Rose, who would eventually invite Charlie to join them in forming Elephant Revival. Unfortunately he was unable to heed the call to initially form the band, but continued to grow his career as a side person and session musician in the vibrant music scene of the northeast while adding pedal steel to his ‘bag’ of instruments.

In the fall of 2014, Charlie released his first solo album of original songs, Stowaways. Shortly thereafter he was asked again to join Elephant Revival and gratefully was in a place to accept. He began performing with them in 2015 and continues to perform with the band and various members in their solo endeavors.

Megan Letts

Mama Magnolia

What is it about some musical performances that seem to draw us in and change the very fabric of our being? Some would say it’s in the song while others would say…
it’s more about the performance. The magic lies somewhere between the two, in the nuance of interpretation. Megan Letts knows the value of both and filters every word she sings through her personal experience and what comes out of her mouth is nothing less than raw honest emotion. She sings the full spectrum of the human condition with just as much power and grit, as she does tenderness and vulnerability. Whether she is on stage leading her indie/soul band Mama Magnolia, or singing and directing music for an all star supergroup, she bares her soul and gives everything she has.

Maggie Baker


Maggie finds her greatest meaning and happiness through the pursuit of music. She grew up playing classical piano and singing in choirs, and in college she completed a year-long research thesis…

on the media’s treatment of African-American string-band musicians in the 20th century. Inspired by stories of the African-influenced clawhammer banjo, Maggie bought her first banjo in her early twenties and set out to learn the old-timey rhythmic style. She picked up bluegrass in 2014 and spent many of her off-work hours performing with her brotherly pals in the local band Groundscore. A talented software engineer by day, Maggie continues to dedicate most of her free time her banjo-playing, which is complemented beautifully by her angelic voice.  

Scott Stewart

Floodgate Operators

Scott Stewart began his musical journey in his teens, though he didn’t fully commit himself to music until he was bit by the bluegrass bug at Telluride Bluegrass in 2016. 

He is a singer, guitarist and founding member of Floodgate Operators, a 5-piece jamgrass band out of Crested Butte, CO. He’s had the pleasure of playing all over the western United States and has shared stages with many of his hero’s. When he isn’t performing, you can find him playing in the mountains around Crested Butte and the Rocky Mountain west.

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Owner's Cabin Upgrade

Each of our yachts feature 3 standard-sized cabins, along with one Owner’s Cabin. This roomy Master Suite features a 40% larger living space with a private, en suite master bath. Upgrading to the Owner’s Cabin will not only provide extra living space, but also a larger bathroom, shower and extra storage for all your belongings on the trip. TREAT YO’ SELF! 


*Price includes cabin upgrade for you and your travel partner*