About Us

 

Who is planning these fabulous trips, you ask?

Take a look in the mirror. Okay, no. We're not expecting YOU to do all the work. That is what WE'RE here for. But the point is that WE are exactly like YOU.

Well... WE are like YOU, if YOU are a hip, savvy, successful, finely-tuned (no, don't worry, we didn't say "finely-toned") sister who wants to take trips with her friends? Yes? Perfect.

Kerry Rupp, Founder

Kerry Rupp, Founder

Before starting Holiday Golightly, Kerry spent a number of years in Very Important Professional Positions, which is shorthand for "she really knows what she is doing", in the business sense. She brings over 13 years of strategic planning, marketing, business development and operational management experience from Classmates.com, Jobster, LexisNexis, McKinsey & Company, Sterling Commerce and Andersen Consulting (now Accenture).
View Kerry Rupp's profile on LinkedIn

She has also frequently taken chunks of time off from the crazy corporate world, and traveled in the rest of the world. She holds an MBA from Harvard Business School and a BA from Duke University, and a PhD in Travel. Playtime-having-Degree. Kerry managed to excel at the grown-up jobs, while at the same time planning fun girls' trips for her friends. She then decided to combine the two. And you're welcome.

But, even better, is Kerry by the numbers:

  • 47 – The number of States in the U.S.A. she's been to (although 3 were really just drive-throughs – they still count)
  • 8 – The number of States (in the U.S.A.) she's lived in
  • 3 – Foreign countries she's lived in ( Canada – yes, it counts – Germany and Italy)
  • 46 – Foreign countries she's visited (give or take a few), including 10 in Central America and the Caribbean, 5 in South America, 19 in Europe, 10 in Asia and the Pacific Rim.

Kerry's next mission:
To explore all the varieties of French Fries the world has to offer.

Gretchen Berg, The Voice

Gretchen Berg, The Voice

The first birthday present Gretchen's dad actually bought, all by himself, was for Gretchen's 16th birthday. It was a plain gray sweatshirt with black iron on letters that spelled out "Life Is Fun".

A whole mess of years later (none of your business), not much has changed. That is still her motto. After finishing a 3.5 year tenure at an Expedition Travel company, Gretchen jumped onboard with Holiday Golightly, to write any and all copy for the website, newsletter, email correspondence and assist with other duties as needed.

Gretchen's love for travel began with a study abroad program in Dunedin, New Zealand, and continued with a teaching position in South Korea for a year. She then honed her planning and logistics skills while working with the Semester at Sea program, where she coordinated trips in 12 different countries, and led several large-group excursions in Tanzania, India, and Cambodia.

She spent the last 3 years coordinating and planning travel for trips to some fairly out-of-the-way destinations, such as the Canadian Arctic, the Galapagos Islands, and Antarctica, and has peppered her work-travel with her own self-designed trips to Europe.

Gretchen has been traveling domestically since the age of 3, and internationally since her college study abroad experience, and has stopped just long enough to pay some bills and make sure her parents were still keeping her stuff in their garage. They're not.

Gretchen's next mission:
To own one pair of shoes from every country in the world.

 bulletWhat will Holiday Golightly do for me, you ask?