Pillaging the High Seas with Pro Skaters and Musicians: The 2025 Flogging Molly Salty Dog Cruise

Once again the high seas were swashbuckled—by now you’ve surely heard of Flogging Molly’s Salty Dog Cruise they’ve been running for the last decade. Where else can you board a cruise ship with the likes of Matt Hensley, Christian Hosoi, Steve Caballero, Justin Strubing, Brian Schaefer and the Skatepark of Tampa crew, Dave Duncan, Jimmy The Greek, Collin Graham, Jason Adams and whoever else might be walking up the gang planks to cruise the Caribbean skating and watching live music all day every day?

Dave Duncan, always the master of ceremonies, with our fearless leader, Matt Hensley.

Blair Alley

For the musical portion of this year’s cruise, we were treated to multiple live performances by The Bronx, members of Flogging Molly playing traditional Irish music, The Gaslight Anthem, The Living End, FIDLAR, The Devil Makes Three, Me First and the Gimme Gimmes, The Aggrolites, Good Riddance, Street Dogs, Scowl, Riverboat Gamblers, The Tossers, Sprints, The Cherry Cokes, and of course Punk Rock Karaoke. In a possibly fool hearty mission, yet striving to keep things old school and analog, this voyage was captured exclusively on film.

Flogging Molly’s fearless frontman Dave King was MIA this year due to a freak medical emergency, so Flogging Molly as a whole didn’t perform. We received the reassuring news while onboard that Dave was on the mend and the positive vibes flowed from island to island. Flogging Molly members Matt Hensley, Nathen Maxwell and Dennis Casey did however perform acoustic sets of traditional Irish music. And there was a mega-medley on the topside pool deck where all of the bands in attendance did FM covers with different members of the band coming on to join them. An epic performance indeed.

Mariachi El Bronx on the topside pool deck stage!

Milada Rakijian

Upon washing up on Grand Cayman shores, the Black Pearl was still standing! But alas, we couldn’t skate ‘er. After a quick call was put into to sometime-local Mark Appleyard, local transport was provided in the form of Aric Holtz and Mark Berry. The two land lubbers took us to their blossoming DIY named “Mariners.” A day was had: a backyard mini, the island’s best fish shack, and a dip in the briny before being tendered back to the mothership. It was Brian Schaefer’s birthday so of course magic was in the island air.

Straight off the boat in George Town, Sergio nosebonks the barrier.

Blair Alley

Thar she blows! Thing is, some developers bought her and she’s scheduled for demo.

Blair Alley

Crew jammed up. “What should we do next?” “I got some numbers from Appleyard…”

Blair Alley

Paradise found! “Mariners” DIY.

Blair Alley

Sergio gettin’ up over Strubing and Schaefer for a SPoT Life episode, maybe?

Blair Alley

Frontside 180 over whatever’s in the way.

Blair Alley

Jimmy the Greek hoists a backside boneless.

Blair Alley

Justin Strubing with a picture-perfect pivot to fakie in paradise.

Blair Alley

Over to neighbor Dave Wilson’s with the perfect size mini in the backyard. Strubing, pivot.

Blair Alley

Strubing decks a front rock.

Blair Alley

Head dunk! Dave’s got the best backyard on the island.

Blair Alley

Aric and Jimmy hit Aric’s local beach to cool off.

Blair Alley

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The day after Grand Cayman, our crew got marooned on the irie island nation of Jamaica. Some opted for the Ocho Rios waterfall tour while others relaxed and sipped Red Stripes on the nearby beach. Jamaican me crazy.

There was no skating in Jamaica so all you get is this photo off the bow.

Blair Alley

Soon enough we were all aboard for the last day on the Norwegian cruise ship bound for Miami. We deboarded in a haze of skate sessions, late nights, and memories that will last a lifetime. Trips like this with your skate homies from around the world—nothing gets better.