Andrew McMahon’s Second “Holiday From Real Cruise” Sets Sail From Miami [Photos]

From February 28th to March 3rd, 2026, Andrew McMahon’s sophomore Holiday From Real Cruise set sail from Miami, Florida, to Puerto Plata, Dominican Republic. The cruise follows November 2024’s first voyage in collaboration with Sixthman, known for their music-festival-on-a-boat style cruises, and Norwegian Cruise Lines. This year’s sailing took place on the Norwegian Pearl, an upgrade from the previous Norwegian Gem, allowing even more guests to take part in the vacation of a lifetime.

The 2026 lineup included McMahon’s three bands, Something Corporate, Jack’s Mannequin, and Andrew McMahon in the Wilderness, alongside a selection of artists and bands to cater to fans of any and every era of the host’s storied career. Over the course of four days, attendees had plenty of opportunity to see their favourites on the lineup over and over again, or to branch out and find some new music they’re into. On top of an abundance of music, other entertainment on board included a “swag swap” for crafty fans to trade homemade goods like friendship bracelets, a dedicated crafting corner, multiple artist-led activities, and even resident tattoo artist Craig Beasley for those wanting a more permanent memento of their trip.

Saturday, February 28th:

Day one’s music kicked off with a performance from The Rocket Summer in the Atrium, the ship’s main lobby, to greet guests as they made their way aboard. The party truly got started with a sailaway set from Something Corporate on the Pool Deck, the biggest venue board designed to fit the entire 2,300+ capacity of the Pearl. With the sun high in the sky and temperatures in the 80s, it felt like the ideal carefree summer afternoon despite being in the midst of winter, and the perfect way for passenger to leave their worries on land for a few days in the sun. Following McMahon’s first performance of the voyage, guests then had the opportunity to choose their own adventure for the rest of the day.

Folk-pop trio Trousdale took over the Atrium, while singer-songwriter Ivory Layne set up shop in Magnum’s, and Petey USA headed over to the Stardust Theater. Poor weather, unfortunately, forced the cancellation of The Maine’s Pool Deck set, which was later rescheduled to the final day of sailing. Flor brought the vibe straight back up in light of the cancellation with their set in the Atrium; the band is known for their boundless energy and infectious joy, and it certainly shone through despite the gloom outdoors. The Starting Line then closed out Stardust, while “pop-punk piano man” Hunter DeBlanc finished the night of music at Magnum’s.

DeBlanc is a seasoned cruiser at this point, having made a name for himself on various cruises across the globe with his unique style mashing up crowd favourites from the 1990s to the early 2000s on the spot. He was a fixture on the first Holiday From Real Cruise in 2024, and as a longtime fan of McMahon’s himself, was only too happy to return in 2026. For those wanting to keep the party going, Silent Disco up in the Spinnaker Lounge went on until 2 am.

Sunday, March 1st:

Day two was spent entirely at sea, and while some may have preferred a slower start to the morning, Flor was out bright and early for “Run The Flor,” which is pretty much exactly what it sounds like; cruisers who signed up in advance joined the band’s vocalist, Zach Grace, for a jog around the ship’s running track. Other morning festivities included “Say It Like You Mean It: A Conversation With The Starting Line” as well as a fun game of “Finish the Lyric” hosted by Ivory Layne. The day’s music started on the Pool Deck just after noon, with a delightful “Prom Queens” set from members of Something Corporate and Jack’s Mannequin.

The set is a response to 2024’s extremely well-received acoustic performance from William Tell and Brian Ireland of Something Corporate, only bigger and better this time around. Tell noted that he, Ireland, and some other friends had recently gotten together to play a set of prom favourites at his wife Lauren Conrad’s 40th birthday party, and so it only made sense to rehash that set. From “Hot To Go” to “Champagne Supernova” and, of course, “Thong Song,” the set was one of the most entertaining of the entire cruise.

The rest of Sunday’s schedule was jam-packed with music, featuring Michigander and Trousdale on the Pool Deck, Annika Bennett and Flor in Stardust, The Rocket Summer, Bikelock, Petey USA, and Zac Clark in the Atrium, and Polyglam and Ivory Layne in Magnum’s. More activities included a live taping of The Gunz Podcast, a cocktail class with The Maine called “Can’t Stop, Won’t Stop Drinking,” karaoke hosted by Gunz, and a guest DJ set by Bryce Avary of The Rocket Summer at Silent Disco.

Of course, the evening wouldn’t be complete without a performance from McMahon himself, who took the Pool Deck with Jack’s Mannequin to continue the chronological journey through his career. Much to the delight of his most devout fans, the man took feedback from his Camp Wilderness fan club to heart and worked in some deep cuts into his sets on the cruise; the Jack’s set saw the first performances of fan-favourites “Keep Rising” and “Meet Me At My Window” for the first time in likely over a decade.

Monday, March 2nd:

Monday was the cruise’s only port day, docking at Taino Bay in Puerto Plata in the early hours of the morning. Cruisers had the options of either staying on the boat, booking an excursion, or enjoying the amenities at the port itself, which included local cuisine and a lazy river. After a relaxing morning and afternoon on land, it was all aboard at 5:30 pm, with music kicking off with The Starting Line on the Pool Deck shortly after. Trousdale and Annika Bennet took over Stardust and Magnum’s, respectively, while Michigander led a wild and hilarious “band practice” style performance in the Atrium. The set included numerous special guests from other performing artists, as well as frontman Jason Singer taking a step back to let his bandmates each lead vocals on various covers, humorously claimed as their own, including The Killers’ “When You Were Young” and Oasis’ “Wonderwall.”

McMahon took to the Pool Deck stage once more with the first full Wilderness set in quite some time; after a few years of chasing nostalgia with his former bands, the return to his present project was welcome and refreshing for fans new and old alike. Highlights of the set included rarely-played tracks like “After the Fire” and “Lottery Ticket,” and a guest appearance by Ivory Layne to sing harmony on “Dead Man’s Dollar,” a track which she co-wrote for 2016’s album Zombies on Broadway. While McMahon is known and beloved to his fans for his immeasurable kindness, he somehow managed to outdo himself yet again by inviting cruiser and violinist Cindy Carrier on stage to perform “Something Wild” with him and the band.

Carrier is a middle and high school orchestra teacher who made herself known to McMahon via Instagram videos she shared of her students performing her own string arrangements of McMahon’s music. The night ended with a Stardust set from The Maine while Hunter DeBlanc took Magnum’s, the latter of which included guest appearances from Bryce Avary as well as McMahon himself.

Tuesday, March 3rd:

The final day of cruising was again spent entirely at sea, and though it may have been bittersweet, an action-packed schedule left little time to despair the impending end to the trip. Annika Bennett started the morning off with a game of Bingo in the Spinnaker Lounge, followed by a party on the Pool Deck, DJ’d by Hunter DeBlanc. The party also included the return of 2024’s infamous belly flop contest, judged by McMahon and a handful of other performers. The contest culminated with a push-up showdown between McMahon and a returning cruiser, who wagered a donation to the host’s own charity, the Dear Jack Foundation, and ultimately won.

After the party, Gunz hosted a game of Who Wants To Be an Emo Millionaire? while Bob Oxblood of Jack’s Mannequin played a chill set in the Atrium. McMahon returned to the Pool Deck for a “behind the songs” Q&A session hosted by Gunz, featuring questions from various cruisers. The talk revealed that the Holiday From Real Cruise will return in 2028 on a bi-annual schedule, as well as a vulnerable moment in which McMahon shared his anxiety about performing at an upcoming Billy Joel tribute concert. Petey USA, Trousdale, and Ivory Layne then participated in a thoughtful mental health panel discussion up in the Spinnaker Lounge, discussing the emotional difficulties a career in the arts can bring, as well as the challenges of simply being a human being in a chaotic world.

Flor and Annika Bennett delivered their final performances of the cruise in the Atrium and Magnum’s, respectively, followed by the long-awaited Pool Deck set from the Maine. The Rocket Summer and Polyglam then finished their sets in Stardust and Magnum’s, followed by Petey USA on the Pool Deck, and Michigander and Ivory Layne in Stardust and the Atrium. Finally, McMahon took to the Pool Deck stage one last time for the return of the “Andrew McMahon and Friends” style set. This performance featured a smattering of guests, not only from his different bands, but from other performers on the cruise. Polyglam’s Allie Stamler joined McMahon on violin for a gorgeous rendition of “Me and the Moon,” performed beneath a breathtaking full moon, lighting up the night sky.

The two also played “I Heard Your Voice in a Dream” together; the song is something of a white whale for many of MaMahon’s fans. Released in 2013 and penned for the Broadway-inspired TV series SMASH, McMahon has only performed the song live a small handful of times, though it is widely adored by his most devoted fans. The set also included a rehearsal of Billy Joel’s “Piano Man” in preparation for McMahon’s Carnegie Hall debut the following week, as well as a cover of The Grateful Dead’s “Friend of the Devil.” Finally, McMahon brought out all the members of his different projects, as well as several of his closest friends on board, to close the Pool Deck with a rendition of “Teenage Rockstars.”

For those chasing the final hours of vacation, The Starting Line finished out the Stardust Theater with one last performance. Hunter DeBlanc took to the Atrium for one more set, this time with a more intimate vibe, showcasing some of his own original music for the first time on the cruise. Karaoke with Gunz kept going into the night, and even featured a guest performance by McMahon and Something Corporate’s Josh Partington as they partied the night away, and of course, Silent Disco kept the vibes high into the wee hours of the morning.

Though cruisers may have disembarked the ship in the morning physically drained, just about anyone who had the fortune of attending will tell you they left the trip feeling emotionally rejuvenated and with full hearts. From countless tired faces and wide smiles, the most common departing sentiment was unanimous – see you in 2028!