Cruising to a New Career

Image: PHOTO: A fateful cruise vacation altered Tracy Whipple's career trajectory. (photo by Jason Leppert)
Image: PHOTO: A fateful cruise vacation altered Tracy Whipple's career trajectory. (photo by Jason Leppert)
Lisa Iannucci
by Lisa Iannucci
Last updated: 7:00 AM ET, Mon January 22, 2018

Tracy Whipple was working as a paralegal when she found out her job would significantly change right before she was to leave on a three-week cruise vacation.

However, it wasn't all bad.

"While I was on the trip, I met someone in the travel industry who suggested that I would be good working with an agency arranging group trips,' said Whipple. "It sounded like fun so I looked into it more."

Not long after the cruise, she was hired by that agency to handle group cruises.

"As part of the job, I learned everything I could about booking travel," Whipple said. "I picked it up very quickly and started handling reservations in addition to the group activities. As my client numbers grew, I realized I enjoyed handling both groups and individual reservations. "

Today, she's been in the industry for 11 years but admits the idea of booking travel did not initially appeal to her.

"Since the agency was mostly Disney focused and I wanted to offer more, I left that agency after four years and started Travel On A Dream," said Whipple, who is based in Deforest, Wisconsin.

She has a hands-on approach to business and said many of her clients come through referrals, so she doesn't do much marketing: "It did take time to grow, but I find the potential clients that do come to me are more likely to book than those who found me through our website."

Whipple decided to specialize in groups and cruises as that was her passion and the reason she started in the industry: "I've learned as much as I can about the cruise lines I sell as well as the ships in their fleet, always looking for new information to better serve my clients."

When she's not working hard, Whipple loves to cruise, though it pretty much doesn't matter where: "Just being on a ship and enjoying the ocean is my way to relax."

Her favorite cruise destinations have been Alaska and Iceland, though the Panama Canal is a must-do as well.


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Lisa Iannucci

Lisa Iannucci

Lisa Iannucci has written many travel articles for national magazines and newspapers. Over the years, her travel articles have...

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