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Sage Hill Alumnus Sets Sail As Luxury Cruise Line’s Destination Planner

By Daniel Langhorne
Jess Peterson ‘09 raced with Sage Hill’s sailing team as a student, but he still doesn’t consider himself an expert on the high seas. However, this foundational knowledge of vessels has informed his role planning and vetting experiences for the cruise industry.

As Director of Destination Experience & Itinerary Planning at Windstar Cruises, Peterson is charged with ensuring customers aboard a “small ship” fleet – embarked with 150 to 300 passengers per vessel as opposed to thousands –  adore layovers from the South Pacific to the Panama Canal to the Baltic Sea.

“I get to think about travel all day,” Peterson said. “And for me, the cruise business is very fun because it combines travel and logistics and also hospitality.”

Peterson also relishes working with people from all over the world but sometimes that comes with hiccups. While some workers might get snarled in traffic on their morning commute, cruise operators need to pivot in the face of hurricanes, civil unrest and war.

“World events directly affect what we do,” Peterson said. “Honestly, sometimes it's sad. Some bad thing happens somewhere, and then we have to adapt but it definitely makes [the work] interesting.”

Peterson traces a love of cruises back to his childhood, which included his family setting sail at least every other year.

“My grandma would take us on cruises when we were growing up, and I was a huge nerd about it and I just loved it,” Peterson said. “I would order all the brochures and memorize the schedules and memorize the deck plans.”

While earning a bachelor’s degree in history from Stanford University, Peterson applied for an internship at Carnival Cruise Lines.

“They turned me down because they didn't believe that I would move to Miami. I was obviously very defeated and then the next year, I just tried again, and then they realized, ‘this person's persistent,’”
Peterson said. “I do think that it's a good example of not letting a small setback kind of change my trajectory.”

He went on to hold various positions in itinerary planning and customer experience at Holland America Line and Hurtigruten Group. Building relationships with other professionals in the cruise industry has been key to getting hired at every job, Peterson said.

At Windstar, he’s enjoyed acting as a lead planner for trips to Asia. Angkor Wat, Hong Kong and Kyoto are just a few of the fleet’s destinations in the Western Pacific.

On a personal level, Peterson relishes expedition travel, which has brought him to the icy wasteland of Antarctica and the surreally beautiful Galapagos islands.

Looking back on his Sage Hill years, Peterson feels grateful for how teachers fostered his curiosity about information, history and other people.

“People were just very kind to each other, generally speaking, and obviously teachers had a lot of time for us and other things,” he said. “But even just the way students interacted with each other was overall very kind. In that approach to the world, the travel industry is pretty similar.”
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Sage Hill School

A college preparatory independent day school for grades 7-12.

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