Life at Sea: Marrying a Cruise Ship Entertainer

1. Life on a Cruise Ship

2. An Unexpected Journey

3. The Unique Role of Guest Entertainers

4. Memorable Experiences

A behind-the-scenes look at my life sailing around the world with my husband, a cruise ship performer.

Photo: Vanessa Armstrong/iBestTravel

My husband might be the only magician who has ever stepped onto the stage of a 1,000-seat theater and received a standing ovation for a trick performed with dental floss. This performance was his 14th on a cruise—an unprecedented number given the extraordinary circumstances. It certainly encapsulates the essence of being a cruise ship entertainer: regardless of the situation, the show must go on.

I have a confession: For most of my life, I never wanted to go on a cruise. The thought of being on a large vessel drifting across the vast oceans felt both claustrophobic and overwhelming. Wouldn’t it be better to keep my feet on solid ground?

However, everything changed when I visited the Magic Castle in Hollywood and met a magician named Jon at the bar. Fast forward 10 years, and I find myself married to that magician. In the last decade, I’ve had the privilege of traveling with him globally as he performed with various cruise lines, including Viking, Seabourn, Oceania, Crystal, Azamara, and Disney. Furthermore, I’ve had the opportunity to taste the waffles on each cruise and can certainly share which line offers the best taste.

A man on stage on a cruise ship
Vanessa Armstrong/iBestTravel

Being a guest entertainer on a cruise ship is one of the many opportunities for magicians to earn a living. Unlike the excellent crew who may stay on a ship for several months, guest entertainers typically board for just a week or two before moving on to the next destination. Jon and I have traveled to various global locations thanks to his performances, from Antarctica to the Panama Canal, along with several trips to the Caribbean and Alaska. Notably, while entertainers are primarily treated like other guests—sharing cabin types and dining in passenger restaurants—substantial differences exist in our cruise experiences.

The most significant difference guest entertainers encounter (aside from always working rather than indulging in a relaxing vacation) is that they do not usually embark and disembark with the same passengers. Almost every cruise has had us boarding in the middle of a journey and either leaving halfway through another trip, enabling them to perform for two diverse sets of guests, or disembarking before the voyage concludes, giving passengers more opportunities to enjoy various acts.

This ‘midshipping’ sometimes asks us to travel to remote locations to catch a ship. Once, while joining a world cruise, we had to fly from Los Angeles to Santiago, Chile, followed by a multi-hour bus ride to reach the ship. After 36 hours of travel (and no shower), we finally arrived at the port, where we waited an additional hour to navigate customs. There was confusion about which manifest applied to us: crew or guest. (In case you’re curious, the answer is guest, although explaining Jon’s role as an entertainer brought on understandably puzzled reactions.)

My designation—the guest of a guest entertainer—presents even more confusion and is further complicated by ensuring compliance with a 100-plus-year-old law. Enacted in 1886, the Passenger Vessel Services Act mandates that guests cannot embark or disembark from a cruise at U.S. ports unless the ship has docked at “distant foreign ports” in between. This law exists for reasons still debated; however, the good news is that most regular guests are not significantly impacted due to cruise companies’ adherence to compliant itineraries. But when midshipping on an Alaska cruise, for example, there’s a genuine risk of violating the rule. Fortunately for Jon and the cruise lines, this applies solely to me while traveling, and it has complicated our plans on several occasions—sometimes even after tickets were purchased.

Once we board, any travel frustrations dissipate into sweet memories. Each voyage creates a unique community, and until Jon’s first show, we blend in seamlessly with the other guests. Following his opening night performance, however, our status elevates, and we become somewhat of mini celebrities among passengers. Jon enjoys performing quick card tricks for guests who approach him, as long as he’s not eating or, more recently, chasing after our toddler.

A family photo and a man and woman under a directional sign in Antarctica
Vanessa Armstrong/iBestTravel

Throughout our journeys together, several experiences stand out distinctly. For instance, in 2018, we cruised to Antarctica, allowing Jon the privilege of claiming he has performed on all seven continents.

The cruise where Jon received his standing ovation for the dental floss trick was unlike any other. In March 2020, while sailing through the Panama Canal, we had originally planned to disembark in Bolivia when we docked, but the world shut down shortly after we left New Orleans. Ports were completely closed, preventing any new entertainers from boarding. With several days at sea ahead, there was a strong desire to keep passengers entertained. Typically, Jon performs three shows on a cruise: one main stage performance, one adult show, and one workshop. But during this unique trip, he performed three stage shows, four close-up shows, three adult shows, and four workshops. By performance number 14, he was down to dental floss as his only prop.

Currently, Jon is back on cruise ships, although my trips (and waffle tastings) with him have diminished since our daughter was born. Our almost three-year-old has already enjoyed five cruises, with many more anticipated in the future. Our experiences have naturally evolved, but witnessing her joy as she watches Jon perform in the theater is incomparable. We sit at the back, and as the audience rises to applaud, she enthusiastically shouts, “Daddy did it!”

And if you’re curious about which cruise line has the best waffles: it’s Viking, although the Mickey-shaped ones served on Disney cruises certainly possess their own charm.

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