Cassandra Bookholder


A native Aussie, Bookholder has spent a great deal of time Down Under, traveling around her home country as a child before studying tourism and business in New South Wales. Today, she's based in San Diego and returns at least two or three times a year to search for new ways to experience old favorites, like adrenaline tours of Sydney featuring seaplanes, motorcycles, and jet boats. Recently, Bookholder has seen an increase in trips that offer experiences for travelers who want to feel completely away from it all. In New Zealand, she loves the brand-new Lindis lodge on New Zealand’s South Island, which provides that “middle-of-nowhere” atmosphere (and which has some particularly good hiking), but still within an easy 2.5 hour drive from the adventure capital of Queenstown.

There has also been an increased interest in getting the kids involved on these epic adventures, with clients wanting experiences together as a family. Bookholder can arrange shark feeding off Ned’s Beach on Lord Howe Island in Australia or an Aussie football lesson in the suburbs of Adelaide. She’s also begun creating itineraries that meet the interest of her clients for a local, insider’s view on a destination, like a day or two on Waiheke Island near Auckland (the city’s answer to the Hamptons as a summer playground).

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Highlighted Review

"Cassandra Bookholder provided us with the trip of a lifetime.  She knows Australia inside and out.  We swam with sharks, rang in the New Year from a penthouse over Sydney Harbor, pet koalas, fed kangaroos, and dined at both fun local haunts and Relais & Châteaux destinations.  Every detail of our trip was curated for our family from private bike and wine tours to our own villa on the Great Barrier Reef.  She provided superlative service at every step of the way.  We cannot recommend her highly enough." - Stephanie Lofgren

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