Rhythm & Sails 2023: An Intimate Week Of Music On The Caribbean Sea

Members of Greensky Bluegrass, Fruition, The Infamous Stringdusters and more were among the participants.

By Court Scott Jun 6, 2023 • 11:03 am PDT

Photo by Jay Nel-McIntosh

Imagine spending a week, both on land and at sea, carried along your tropical journey by a soundtrack from five astoundingly talented musicians, hopscotching the islands of Saint Vincent and the Grenadines aboard luxury catamarans with 36 of your soon-to-be close friends.

If you can imagine, then you can manifest it because Rhythm & Sails charters are offering the most bespoke, intimate music-centric adventures in the game right now, and I was fortunate enough recently to get on board.

The entire experience was wholly amazing, incredibly well-oiled, and as personal a musical experience as one could ever dream of. Acoustic live music on beaches and in bays, under the sun and beneath the stars, being gently rocked by the sea, or simply the sound of the waves reaching the shore – it's how dream vacations are born.

Rhythm & Sails is the extraordinary brainchild of Ashley Hart, Damian Quigley, and Anders Beck. Hart grew up sailing in the Caribbean and has substantially extended roots in the islands, and manifesting music in the area is a demonstration of his love not only of the land and the people but of sailing. His passion is as genuine as it is contagious.

Photo by Ele Hart

"I’ve been sailing through Saint Vincent and the Grenadines for decades," said Hart. "During one trip we spent hours playing music, connecting and laughing with friends in Salt Whistle Bay, Mayreau and there was a moment where I realized this is what I wanted to do for years to come – to bring incredible people and musicians together in this utopia."

Quigley's expertise in operations and production is the backbone for the breathtakingly gorgeous and unique adventures, while Beck serves as the music director, assembling and leading the "house band." Together, these three create a magical vibe that you can simply step into and be carried away.

Photo by Ele Hart

The real adventure began after a four-hour flight from Miami to Saint Vincent, the largest island in the Grenadines chain, located 1,500 miles southeast of Florida – closer to South America than North America. After meeting up with several fellow sailors and clearing customs, we were seamlessly taxied over to the marina where our boats awaited us.

Our flotilla for the upcoming week was made up of three sailing catamarans – Fantasea, White Bird and Bare Necessities. Each dual-hull, four-bedroom boat had a crew of at least three, including a captain, first mate and chef to attend to guests – 36 people in all – as well as dinghies to ferry us between boats and land.

Photo by Ele Hart

Sailors were composed of both couples and singles, with slightly more women than men. Initially, the gathering felt somewhere between getting to know your camping neighbors at a festival and speed dating, but as the week progressed, we started to enjoy each other's presence more and vibe on a deeper level, with strangers becoming family.

We had five sailing days, two overnight days to relax and explore, and went to six islands, where day or night – sometimes both – our house band, Anders Beck (dobro, Greensky Bluegrass), Travis Book (bass, The Infamous Stringdusters), Mark Morris (guitar, Rapidgrass), Megan Letts (ukulele/keys, Mama Magnolia), and Jay Cobb Anderson (guitar, Fruition) – would play acoustic sets aboard the boats or on the sand of beaches where we moored. The final night was the exception when the band played two fantastic electric sets at Basil's Bar on a small Mustique Island pier.

While the itineraries between weeks one and two were similar, small tweaks were made along the way to ensure each trip was unique. Also distinctive between the two weeks was the musical lineup.

Week one featured many of the same musicians as week two, including Beck, Anderson, Letts and Morris, but also saw Paul Hoffman (mandolin, Greensky Bluegrass), Charlie Rose (banjo, Elephant Revival), and Maggie Lincoln (banjo, Groundscore) in the band, which created a significantly different musical experience from week two.

Photo by Ele Hart

Due to the remote location of the Grenadines, at the southern end of the eastern border of the Caribbean Sea, where it meets the Atlantic Ocean, each night we were able to see the Milky Way, many of us for the first time. Cloaked in expansive, velvety black, the familiar Big Dipper hung in the same night sky as the Southern Cross and many other constellations not visible from the northern hemisphere.

And it was under that backdrop that the band, whether composed of a duo, trio, quartet, or quintet, played a range of tunes. From numerous stunningly beautiful originals – some even written on the boats during the trip – to an eclectic catalog including tunes from John Prine, Phish, Willie Nelson, Sublime, Pink Floyd, AC/DC, The Grateful Dead, Tina Turner, TLC, Simon & Garfunkel, Sturgill Simpson, The Rolling Stones, Kris Kristofferson, David Bowie, STYX, Bob Marley, Bill Monroe, and many, many others. As the week progressed songs and lyrics were perfectly curated, mashed up and allowed space to bloom while the rawness of the acoustic instruments was perfectly matched by the natural surroundings.

Photo by Ele Hart

All the musicians had striking voices, but perhaps the most enigmatic was Megan Letts, who is positively magnetic when she's in her element, which is often. Equally enchanting were guitarists Jay Cobb Anderson and Mark Morris, both of whose playfulness surprised and delighted.

I was completely stunned to see a full-size upright bass standing in the sand and on the boat, but Travis Book brought it wherever the band went and handled it just as he would on stage at Red Rocks. This was also the first time I’d really had the opportunity to really check out a dobro (resonator guitar) in action, and it was fascinating to watch Anders play dipping in with harmonies, gently leaning into the other musicians.

Photo by Ele Hart

From Day One, there was an overwhelming sense of gratitude; everyone knew that what they were experiencing was something truly special and utterly unique. While there are other at-sea musical adventures, none are as unique as Rhythm & Sails’ offering with seamless execution and careful attention to detail. Nor are any quite so intimate, with the line between performer and audience blurred, if not erased. As an attendee, I couldn't help being aware that I, and others, were an equal part of each musical moment. And nearly everyone in attendance I asked said they’d do the trip again in a heartbeat, even the musicians who’d been at sea for two weeks back-to-back.

The seven-day tour had stops in Bequia (pronounced Beh-kway), Mayreau, itty-bitty Mopion, the Tobago Cays, and Mustique, before returning to Saint Vincent. For the most part, the seas were calm, and the sails carried us, averaging 8.5 knots/hour (~10 mph) with no day's sail longer than four hours. Folks could learn as much as they wanted to about the mechanics of sailing; staff were 100% accessible and shared their knowledge freely and many sailors were born. The weather was stunning, and we didn't see a drop of rain the entire week.

Photo by Ele Hart

The very first evening – night one – after a thorough safety briefing, we relaxed, ensconced in beanbags on the top deck of the Fantasea under a wildly starry sky, and were treated to a remarkably intimate show with the full band.

Photo by Jay Nel-McIntosh

The next morning, there was time for breakfast and snorkeling off the boats before a quick one-and-a-half-hour sail for the island of Bequia, where the Anders Beck Golf Invitational, a rowdy golf tournament at the Firefly resort, took place. With cold beers in hand and after numerous stops under The Rum Tree, a winning team was declared after an initial tie and foot race to the pool to determine the victor.

After the tournament, Anders Beck and Travis Book – "just two buddies from the mean streets of Durango Colorado," played an intimate set of mostly original tunes.

Photo by Jay Nel-McIntosh

On the morning of day two, we left Bequia's Admiralty Bay and set sail for the island of Mayreau – about three hours south. We tethered to mooring balls in pristine Salt Whistle Bay, a quintessential tropical island destination with a sugar sand beach around turquoise water, rimmed by palm trees.

There was a light afternoon jam on the sand, followed later by Rock Star Night. Everyone dressed in costumes for a multi-course barbeque at a rustic local restaurant and bar, followed by a second set with all five musicians, subsequent karaoke, and a nighttime paddleboard extravaganza.

Though the music was primarily acoustic, the production value was impressive: the Rhythm & Sails crew packed in a case of battery-operated, iPad-controlled can lights, dinghied into each evening's performance so that each night felt like a true concert experience. Later, the team would set up the lights throughout rotating host boats for dance parties that ran into the small hours.

Photo by Ele Hart

I quipped one day to the crew that each day was like peeling back another layer of an onion, but it's apt: every day was orchestrated and carefully organized to wow each preceding day. Each morning a daily schedule was posted and the amount of care and precision that went into the timing and execution of events – as well as the planning that went into each day's cuisine – was impressive.

The food we ate along the way was locally sourced – fish, baked goods, ice, and goods from other vendors – with large-scale provisioning done in Kingstown. We ate like kings with scrumptious breakfasts, tasty lunches, elaborate charcuterie boards, and delicious dinners on the boats as well as three amazing evening meals on land.

Photos by Jay Nel-McIntosh & Ele Hart

The commitment to a strong hospitality game is evidenced here by a brief inventory of the beverages for the week-long charter: 65 bottles of rum, 70 cases of Hairoun beer, 100 cases of non-alcoholic drinks and mixers, 140 gallons of fresh water, a huge collection of non-rum spirits. Nobody went thirsty.

The second day in Salt Whistle Bay was a layover day and for six of us PADI-certified divers, an opportunity to do a two-tank SCUBA dive on the reef surrounding Mayreau. The second dive of the day – a drift dive – was at a site called Mayreau Gardens and ended up being one of the most visually stunning, psychedelic dives I’ve ever taken. With wildly vibrant species living on the coral reef, as well as turtles, lobster, and numerous species of fish, rays, and sharks, I was wowed to see so many colors underwater that simply do not exist above the waterline.

Photo by Jay Nel-McIntosh

That evening, the boat chefs created a magnificent spread on the beach, and all five musicians played a set under a thatched-roof pavilion that had amazing acoustics. It was surprising that while none of the instruments or vocals were mic’d until the final evening, each instrument – including the stand-up bass – rang out clear, with the soundwaves not swallowed or distorted by the sand or sea.

After leaving Salt Whistle Bay the following morning, we made a pit stop on tiny Mopion Island, a pure white sand bar surrounded by tropical reefs with a single thatch umbrella for shade. Pirates of the Caribbean: Curse of the Black Pearl featured the island, and so of course, we had the inaugural Jack Sparrow 0.01k, with Eddie Lucas of TV show Below Deck, taking the win. If seeing a world-class band perform on a 100-foot-long island in the middle of the Caribbean Sea was on your bucket list, you could’ve crossed that off.

Photo by Mike Arzt

After re-boarding the yachts, we set sail for Tobago Cays, a sea turtle sanctuary and grouping of small islands where we snorkeled among turtles, rays, and shimmering schools of fish. That night, we feasted facing each other at a 50-foot-long table at Romeo and Juliet's restaurant, a Cay barbeque featuring several courses of locally sourced, delicious food. After dinner, Megan Letts and Jay Cobb Anderson perched on a picnic table, and played a lovely set, later joined by Beck, Morris, and Book.

The next morning, we set sail for Mustique, one of the most exclusive and inaccessible islands on the planet. With limited "villas" on the island, the only way to stay on Mustique is to be a guest of a homeowner, stay at the 17-room Cotton House hotel, or to moor your boat in the bay. The morning of our final, full day together some of us scheduled massages at the Cotton House resort while others played tennis at The Mustique Tennis Club, snorkeled, lunched, and sunbathed on the shore of stunning Britannia Bay.

Our final night together was spent at Basil's Bar on Mustique where we had our last group dinner – celebrating an engagement that happened that afternoon! – and were treated to a two-set electric concert. What a way to cap off a truly special week.

Photo by Jay Nel-McIntosh

The trip promised to be "life-changing," and while I initially suspected that was hyperbole, after my phone got wet on day two and spent the rest of the week in a bag of dry rice, I melted into a lower vibration than the fevered, hurried pitch in which I spend too much of my time. Perhaps it was the equatorial light that encouraged me to unwind, the sun gently baking my skin and filling up my vitamin D stores, or perhaps it was being forced for the first time in years, to literally unplug, but I didn't feel like I needed a vacation from my vacation, as is true with other types of multi-day musical adventures. I was recharged and off the boat, I’ve taken with me a newfound slower cadence.

Would I, like others on this trip, go again? Without hesitation, I would! And Rhythm & Sails 2024 dates are set. A seven-day sail will embark on May 4 and will see some artists from 2023 return! The on-sale for 2024 begins on June 13, so mark your calendar if a Rhythm & Sails vacation sounds like one for you!

As Mark Morris sang on the very first night to Willie Nelson's "On the Road Again’ atop the Fantasea, "I just can't wait to get on the boat again /The life I love is makin’ music with my friends / And I can't wait to get on the boat again."