top of page

Travel + Leisure A-List Advisor

Cassandra Bookholder

Bookholder Cassandra.jpg


Though based in San Diego, Cassandra maintains deep connections within her home country of Australia, enabling her to deliver unexpected twists on iconic Down Under destinations — say, river snorkeling in the Daintree Rainforest. And with the popularity of luxury villa rentals on the rise, she’s also a master at not only finding the right accommodation for a specific client, but making sure it’s in the best possible neighborhood. For example, if she has a family looking for an extended stay in Sydney, she’ll secure them a private residence which is within walking distance of Taronga Zoo. “They can keep their four year old constantly entertained but also have easy access in and out of the city via the ferry service,” she says.

Her regional expertise and personal relationships also mean she can handle unexpected logistical challenges without missing a beat. When the bushfires struck during high season, Cassandra quickly shifted a client’s nature-focused itinerary in heavily impacted New South Wales to one in New Zealand’s South Island.


Languages Spoken: English

Number of years on the A-List: 13

Contact Info | 602-266-4000 | San Diego

What is the A-List?

The A-List is Travel + Leisure’s collection of the top travel advisors in the world. Each year T+L evaluates hundreds of luxury travel advisors, vetting each one and receiving input from their Travel Advisory Board (comprised of agency owners & operators) along with other experts to determine which ones will best serve their brands readers.

What is the best time of year to go to the Great Barrier Reef and what is your favorite time of year in Australia?

It’s important to remember that the Great Barrier Reef region has two main seasons – the dry season (comfortable approx. 80 degree weather May-Nov) and the wet season (more chance of storms/rain/humidity higher temps. Dec-Apr). The dry season allowing for comfortable planning of activities whereas the wet (or Green Season) it’s better to allow some flexibility or days at leisure in case changes need to be made.

While the Great Barrier Reef can be warmer in those Aussie Summer months (Dec-Feb) the Southern regions such as Sydney, Melbourne, Tasmania are absolutely ideal for their warm beach/hiking/exploring friendly weather days. Therefore always something on offer no matter the time of year!


How many days should I plan for Australia?

Always a tough question for me to answer. With Australia being a similar size as the US (or Europe) you want to try and plan travel in ‘bite size pieces’. An iconic routing of Sydney-Great Barrier Reef-Ayers Rock (Uluru) you would need at least 10 days. However I really love itineraries where you can swiftly fly in/out and plan great itinerary within 1-2 hours of the city allowing for a shorter (but full/range of experiences) without a heap of transit time involved.  


What do you think about doing Australia by cruise?

Love it! You just need to know what your main ‘wish list’ or ‘end goal’ for the trip is as there is much to do in Australia along the coastline but some may find adding a pre or post cruise few days is necessary to reach some inland experiences. Ultimately though, cruising will allow for a good amount of different landscapes, towns, wildlife in a smooth and ‘unpack only once’ manner.


What can you tell us about kangaroo island after the fires of 2019?

Oh so happy to chat about Kangaroo Island! The island is bouncing back well and there is so much on offer for travelers to experience. Beautifully, much of Australia’s flora can only be germinated by the heat of a fire. This brings a stunning contrast to those fire effected areas (as a child I loved watching the bright green leaves sprout out of a charred black tree). Keeping in mind, half the island was not damaged and is absolutely spectacular. There are kangaroos and koalas, sea lions, echidnas and so much more wildlife ready to check out in their natural habitat. The locals are incredibly eager for travelers to return, these are the beekeepers, winemakers, farmers, eco-guides and more. There is a kind and wonderful community on KI that truly miss us!


We are wine lovers, tell us about Australia’s wine country?

First of all, one amazing point about Australia’s major wine regions is that they are all within 1-2 hours from each major city. Aussie’s love their wine and are incredibly passionate about each step of the grape growing business. With that you can quite often experience a small winery and have the owner sit down and taste with you. There are some amazing vineyards that have world class restaurants onsite but I also love the small café stops in the country where the pastries are absolutely delicious! For those architectural buffs, traveling Australia’s different wine regions (McLaren Vale / Hunter Valley for example) you will be wowed by the interesting designs and thought-provoking layouts. And then, who doesn’t love seeing a kangaroo jump through the vines at sunset…

bottom of page