Lebo’s Yacht Rock: The Inside Story Of An Unforgettable Jam Cruise 20 Set

The star-studded set aboard the MSC Divina on Leap Day was months in the making.

By Scott Bernstein Apr 16, 2024 12:46 pm PDT

As the clock approached 6 p.m. on the final day of Jam Cruise 20, ALO guitarist Lebo (Dan Lebowitz) and an impressive roster of musicians lit into Fleetwood Mac’s “Don’t Stop,” the 11th and last song for the second annual Lebo’s Yacht Rock set. The sun started to fade as the MSC Divina steamed toward Miami and smiles abound both onstage and off. Many of those witnessing the marvelous performance were singing the words to the 1977 hit along with vocalist Shira Elias (Cool Cool Cool, Remain In Light Band).

Lebo – the musical director of the tribute to the genre that took over radio dials in the late 1970s and early 1980s – had perfectly laid out the performance, pulling off all 11 planned songs and featuring a heaping helping of improvisation in the 90 minutes allotted. Months of work went into Lebo’s Yacht Rock set making for a highlight of the musical adventure at sea’s 20th journey.

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So, why Yacht Rock?

“One of the cool things that I really dig is the way music taps into emotional memory,” Lebo explained in advance of the set. “When I think of a time, [for instance] something I did when I was 12 years old, I can think of all the things, I can picture the space and that’s great. It’s all the data points, but those don’t do emotional memory. Whereas music when you hear it and it takes you, it’s not the visual it’s the feeling in your body which is so powerful. Which leads to that music. [Yacht Rock] is the music of our youth, before we were music fans. It’s the shit you hear when your babysitter picked you up after school in third grade.”

It’s that visceral feeling which Lebo seized upon. “The music makes me feel what I felt which is so much bigger of an experience. It’s so much more of a thing than just remembering the past. For me, that music, when I hear those songs, it just totally zaps me to these emotional parts of my life,” he said.

Lebowitz made it clear the set wasn’t about duplicating the songs as much as adding a fresh spin that took advantage of the abundant talent of participating musicians. “I don’t really dig the overly literal things in life. As a musician, especially someone who does lots of different kinds of sets that are themed or fall into the tribute category, I never like to put the costume on,” Lebo said. “I want to honor this music but for us we should express ourselves on it. This music happens to be ripe for that even though it was never intended that way. You can really blow the tunes up which is fun.”

Lebo assembled a core band similar to the previous year’s tribute with a few differences based on availability. The rhythm section consisted of bassist Marc Friedman (The Slip, Ryan Montbleau Band) and drummer Michael Carubba (Cool Cool Cool, Remain In Light Band). Cool Cool Cool vocalists Elias, Sammi Garett and Josh Schwartz did the bulk of the singing along with Lebo. Dan rounded out the main ensemble with keyboardist Chris Spies (Honey Island Swamp Band, Matador Soul Sounds), percussionist Yahuba Garcia-Torres (Remain In Light Band, Percy Hill) and Schwartz’s Cool Cool Cool/The Horn Section cohorts trumpeter Chris Brouwers and tenor saxophonist Greg Sanderson.

“I went to my same core [as last year] because that’s another thing that I like to do with these sets,” the guitarist noted. “My approach is to find a core group that I know and we can get this set built around and then bring guests in on top that come and go.”

Guests who added to Lebo’s Yacht Rock performance on Leap Day (Thursday, February 29) included Ivan Neville (Dumpstaphunk, Keith Richards), Lyle Divinsky (ex-The Motet), Mike Dillon, Viveca Hawkins (Monophonics, Dumpstaphunk), Karl Denson (KDTU, The Rolling Stones), Adryon de León (Orgōne) and Joe Tatton (The New Mastersounds).

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Lebowitz spent months putting together the setlist and communicating via phone and text with participants before the Divina left Miami. The song selection was almost completely different from the first Lebo’s Yacht Rock set.

“There is one repeat because I had a special request for one of the band members,” Dan explained. “Carruba wanted to do [Level 42’s 1985 smash] ‘Something About You’ again. We connected on that tune too because again it takes us to a certain place.”

Yacht rock isn’t narrowly defined in the same way jam music encompasses several genres. “There’s the bullseye which is Michael McDonald’s ‘What A Fool Believes’ that is like the circle of the bullseye. But then there’s this Venn diagram thing which I think honestly in jam music there’s a ton of that,” Lebo said. “What makes jam music jam music? There’s bands on this boat that are totally at home to New Orleans funk people while other bands are at home to country people. But it’s like the Venn diagram in this scene is the center where they collide. That is the funny thing about Yacht Rock and jam music because those Venn diagrams don’t often get pushed together. What we do is the center of that. We love this music that is so perfect but we also like to explore things and jam.”

Once the decision was made to change the setlist, Lebo had a major concept in mind for selecting the songs that would be played this time around.

“I like to pick songs that the cats are going to have a good time playing. Because if everyone has a good time playing, the audience picks up on the joy,” he said. “Pick stuff that’s going to make the band inspired. I’ll follow their inspiration. I like all these songs, so I want to be around people who are pumped.”

Other missions when it came to song selection were how would the musicians be featured? Are the musicians familiar with the songs and tunes that would serve the set well.

“What are the [songs] that satisfy all these cool categories,” Lebo added. “It’s such a puzzle. It’s like Tetris. I love geeking out on that stuff.”

Neville and Divinsky would be showcased on Christopher Cross’ “Ride Like The Wind,” while Hawkins shined on The Pointer Sisters’ “He’s So Shy” and de León channeled Chaka Khan on “What Cha’ Gonna Do For Me.” Ivan enjoyed singing the part of “Ride Like A Wind” originally recorded by Michael McDonald so much that he called it the highlight of his trip.

It was also important for Lebo to play the right number of tunes.

“I want to have enough music for a good, solid set. But I don’t want to put too much in there that makes it a rush and leave time for improvising,” he said. Lebo strategically placed songs that could be well-jammed or kept concise towards the end of the set so he could adjust accordingly. He pointed out the “Don’t Stop” closer as an example.

“It could be expanded on or it could be short,” he said of the Fleetwood Mac cover.

Once aboard Jam Cruise 20, Lebo hosted two formal rehearsals. One was just for the singers to work out the vocal arrangements and the other brought together the core band to run through most of the songs.

“This music is so vocal-heavy and I often do this a lot with bands, I often rehearse harmonies separately,” Lebo said before detailing the reason. “The vocals are so specific of a part with these lush harmonies. If you’re doing rock n’ roll quartet it’s no big deal – but in this kind of thing where there’s a lot of vocals – I’ll get together with the people who are singing harmonies first and we get that all dialed in.M.

“It’s quiet. My guitar is acoustic. We sing and we get everything worked out,” Lebo added. “That way, when we get in there with the band and the louder instruments we don’t have to keep stopping and break the flow.” It goes back to the sectionals from Lebo’s early days in choirs and school bands.

The full-band rehearsal lasted approximately 90 minutes and the featured guests would swing by at pre-planned times to work on their parts. Each of the musicians are consummate pros and it was mind-blowing to watch them figure out the game plan. One particularly cool moment was when the core group rehearsed Toto’s “Africa” with Mike Dillon on vibes. Ivan Neville was in attendance awaiting his turn to rehearse “Ride Like The Wind” and joined Dillon on vibes for the intro to the 1982 hit. It went so well Neville played vibes with Mike Dillon during the actual set.

Despite the time allotted, there were a few songs the band didn’t get a chance to rehearse. Lebo added a third, more informal session and even put together a bit of a cheat sheet for the musicians to use to help them remember the arrangements.

Venn diagrams came up numerous times while talking about the Yacht Rock set with Lebo. One Venn diagram helps display Lebo’s approach to serving as musical director.

“I was at a gig and I looked out in the audience and I saw this guy with a shirt on that had a Venn diagram,” Lebo said. “On one side it said ‘Discipline’ and on the other side it said ‘Surrender.’ In the middle was this cosmic-y looking stuff that said ‘Flow.’ I saw it and I was like, ‘That is the most concise way of explaining my ideal all the time.’”

The fan wound up sending Dan one of the t-shirts which the guitarist considers as a cherished keepsake.

“I’ve always liked to work hard but I’ve always liked to be very open. But there’s a time and place for both. Where you want to be is the ‘flow,’ but it doesn’t exist without ‘Surrender’ and ‘Discipline,’” Lebo said. “I think for the music director role, I’m down to just turn every rock over, see what every option is, talk to each person, make sure they have charts and I’m down with that discipline. But I relish in freedom on stage to just let it all go. That’s what we work on.”

Lebo has gained his music director chops from working with some of the best including years as a frequent member of Grateful Dead bassist Phil Lesh’s bands at the now-shuttered Terrapin Crossroads in San Rafael, California.

“He’s such a conceptual guy,” Lebo explained. “My favorite thing of all those times was when he referred to Grateful Dead as ‘this music.’ He said, ‘with this music, we don’t try to put anything into it. We just try to let it pull something out of us. I said to myself, ‘that’s so deep.’ Are you going to try to get something in there or are you just going to be prepared and open so that something can come out of you, which is so much more pure and inspiring.”

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The set itself came off incredibly well. All 11 songs turned into singalongs and if there were any missed notes or transitions, this writer didn’t catch them.

“It was amazing. I loved how everything went down,” Lebo recalled after the set. “I expected to feel good about it because I knew we had such a good team on stage. I had done a ton of work beforehand to make it groovy and the musicians all took it seriously. They all went the extra mile. So in a way I expected it but you never know what could happen and there’s all these chances when you’re incorporating the unknown of improvisation.”

Karl Denson’s guest spot on the Eagles’ “One Of These Nights” was an example of an element that wasn’t pre-planned. However, Lebo spotted The Stones’ saxophonist in the audience and knew the Eagles song would thrive with the addition of Denson’s sax.

“Even though sax isn’t on the original, in the spirit of this set of ‘doing something with these tunes,’ I thought it could be perfect,’” Lebo explained.

Yet another moment of surrendering to the flow that helped make the set so great.


Jam Cruise 21 sets sail from Miami back aboard the MSC Divina on February 14, 2025. The ship will make port visits to Cozumel, Mexico and Belize City, Belize before returning to Miami on February 19, 2025. The lineup will be revealed in New Orleans on May 2 at the official Jam Cruise 21 Announcement Party.

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