Parrothead Cruise Entertainment

About · Entertainment

We're going to southern islands with a fantastic entertainment lineup!

Jammy Buffet

Onshore at the Parrothead Cruise Bon Voyage Party:

Coming Soon

Dan Sullivan

Dan Sullivan joins Parrothead Cruise 2027 riding a massive wave of success in the Trop Rock world. Hailing from the vibrant music scene of Austin, Texas, Dan recently dominated the Trop Rock Music Association awards, taking home six "Wave" honors including Best Male Vocalist and Album of the Year for his acclaimed project, "Friendships". His soulful storytelling and coastal-inspired melodies have become a staple on Trop Rock radio, earning him a reputation as one of the most compelling and authentic voices in the genre today.

Cruisers are in for an unforgettable experience as Dan brings his signature blend of "island time" energy and heartfelt songwriting to our Southern Cross voyage. Whether he is performing chart-topping hits like "Beachin It" or the fan-favorite anthem "Friendships," his music perfectly captures the spirit of community and escape that defines the Parrothead lifestyle. Get ready to kick back, grab a cold drink, and enjoy Dan's award-winning sounds as we set sail for another legendary adventure on the high seas.

Check out Dan's website to learn more.

Kitty Steadman

Singer-songwriter Kitty Steadman has spent the better part of a decade carving her own path through the Americana scene — equal parts grit, heart, and wanderlust. Known for her powerhouse vocals and vivid storytelling, Kitty first made waves as the frontwoman and primary songwriter for Drop Dead Dangerous (who joined us on Parrothead Cruise 2023), the high-energy Southern rock and roots outfit that earned a devoted following across the country. While her time with the band shaped her voice and drive, Kitty’s solo work reveals a new depth — more personal, more honest, and more her. Her songs balance edge and empathy, celebrating resilience and connection with a voice that feels lived-in and true.

From the songwriter rounds of Nashville to the sun-soaked stages of Key West, where Kitty maintains a performance residency at Margaritaville, Kitty’s shows blend energy, intimacy, and community. Her fans — lovingly known as the Steadheads — have followed her through every musical chapter, from rowdy full-band anthems to stripped-down storytelling nights. Her forthcoming project, The Orchid, recorded in Key West, marks the next evolution of her sound: rooted in her past, but boldly blooming into something entirely her own.

Get to know Kitty here.

Monallo

We are absolutely thrilled to welcome back the phenomenal coastal-folk and trop rock sensation Monallo to the lineup for Parrothead Cruise 2027. If you were lucky enough to catch their unforgettable performance as the sun set at the Parrothead Cruise 2026 Bon Voyage Party in Port Canaveral, you already know the kind of infectious, sun-drenched energy they bring to the stage. For those who missed it, prepare yourselves for a musical escape that perfectly captures the laid-back, "feel-good music done right" lifestyle we all cherish.

Powered by the brilliant trio of frontman and singer-songwriter James Drakes, powerhouse drummer/percussionist Alan Jax Bowers (who also sailed with us on Parrothead Cruise 2026), and groove-master bassist Pete “Pirate Pete” Robertson, Monallo delivers an unmistakable sound that is both deeply authentic and effortlessly uplifting. Since earning the prestigious TRMA Horizon Award for up-and-coming artist of the year in 2024, the band's career has skyrocketed. Blending heartfelt songwriting with beachside grooves, they create an escape reminiscent of the masters of surf and trop-rock, heavily inspired by real-life coastal adventures and a collective love for the sand and sea.

Fresh off the highly anticipated release of their new full-length album Moon and Machine, Monallo is coming aboard with a wave of momentum, chart-topping hits, and a matured, powerhouse sound. Whether they are performing intimate acoustic stories or delivering a high-energy set that gets the whole deck dancing, their music promises to be the perfect soundtrack to our next journey under the Southern Cross. To get a taste of their coastal melodies before we cast off, head over to their website at www.monallomusic.com.

Jammy Buffet

Jimmy Buffett often spoke of “traveling the songlines,” a phrase borrowed from the Aboriginal tradition of mapping the land through music and story—paths that connect people, places, and moments across time. Jammy Buffet picks up that journey, where Buffett’s coastal storytelling meets the improvisational spirit of the jam band world.

Led by singer-songwriter Bob Barrick, with key contributions from Brendan Mayer (who joined us on Parrothead Cruise 2022 along with his father and Coral Reefer Peter Mayer), bassist Zeb Briskovich, drummer Tyler Gwynn, and multi-instrumentalist Mickey Lenny, this Colorado–Tennessee outfit breathes new life into Buffett’s timeless “Gulf & Western” sound. Their live shows offer something for everyone: greatest-hit singalongs for casual fans, deep cuts for the diehard Parrotheads, and cosmic, exploratory jams for those along for the ride. Expect sun-soaked grooves, surprise segues, and barefoot boogie energy from start to finish.

Learn more about these under 40 victims of fate here: jammybuffet.com