Partner Spotlight: Meet Leah Callahan, Itinerary Specialist!


I’ve always admired people who turn their hobbies into vocations, and today I’m introducing you to a friend who has done just that! Leah Callahan and I met in our mutual Marine Corp wife days. Leah works in education, but we’ve been swapping comments on each others travel photos (and fighting over who loves Hawaii more!) for the past few years. I’ve always told Leah that, when she is ready to quit her day job, I would be more than happy to show her the travel planner ropes. While she’s not quite ready to do that (yet!), I recently offered her the opportunity to showcase her itinerary building expertise.

Leah will help me research and build itinerary proposals when you’re looking for a trip that incorporates unique accommodations, active exploration, and off-the-beaten-path experiences. Her passion for unique travel experiences is evident in her photos. I know you’re going to love what she and I plan together!

Let’s learn a little more about Leah!

Age of first trip:

I went on some family vacations, but my first real trip wasn’t until I was 16 when I went to South Africa with school. We spent a week on safari and visited schools, AIDS orphanages, and Robbin Island; my life was changed forever. From then on, all I wanted to do was travel so I could gain new perspective and understanding.

Places you’ve traveled:

I lived in Hawaii on Oahu from 2008-2010. Until then, I never knew how much nature’s beauty could really move me. I worked for a company that did day tours to the volcano on the Big Island, and I made island hopping a priority. I visited all of the Hawaiian Islands during that time so I could enjoy everything Hawaii has to offer.

Since then, I’ve traveled to Mexico, the UK, Spain, Portugal, Iceland, the Canadian Rockies, Singapore, Thailand, and the United Arab Emirates. I’ve spent a lot of time doing what I guess you’d call adventure travel–traveling for the purpose of hiking, kayaking, and other outdoor adventures. After visiting Hawaii’s two national parks, I visited 20 more (plus four in Canada).



Favorite place on earth:

This is so hard for me to choose. Hawaii holds such a special place in my heart. Outside of Hawaii, my top three would be: Table Mountain in Cape Town, South Africa; Vestrahorn in Eastern Iceland; and Redwood National Park. I also really, really love the feeling of the Pacific Northwest and the American Southwest. See! Too hard!


Top of your bucketlist:

This is also so, so hard! I am a lover of the U.S. National Parks and one of my biggest bucket list items is to travel to all of them. So far I’ve crossed off 22 of 59, with my 23rd coming up in January.

Internationally, the top of my bucket list would either be Patagonia, Easter Island, or New Zealand. I’m really hoping to cross one off my list this summer.

Favorite hotel you’ve ever stayed in:

I am very much into finding unique places to stay. I’ve stayed in some great traditional hotels, but for me the quirky, unique spots are second to none. Treehouse Silent Beach on Maenam Beach in Ko Samui, Thailand, was pretty incredible as was Gardar on Reynisfjara Beach in Vik, Iceland. Volcano Teapot Cottage in Volcano, Hawaii, is like a little slice of Heaven.


Favorite drink

House Without a Key in Waikiki is the best place in the world to have a Mai Tai. The Mai Tai tastes that much better with the live music and view of Diamond Head!



I’m a huge believer in utilizing people’s strengths and being a team player; Leah falls right into this – she is my creativity when I’m tapped out and I smooth everything together logisitcally. Thanks Leah for being a part of HCTC!






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