Drew Kluska, founder of The Tailor

Tell us about you and your company.

I’m Drew Kluska, founder of The Tailor. We design bespoke journeys across Australia – hand-stitched itineraries built around each guest’s curiosity, pace, and personality. We’ve been doing this for nearly 30 years now, and our team carries 300+ years of combined in-house knowledge of this country. We work with travellers mainly from North America, the UK and Europe, and collaborate closely with the world’s best travel advisors.

The story of how I got here is probably not what you’d expect. I studied agricultural science at Roseworthy College in South Australia, so I was trained to think about land in terms of productivity, soil, and livestock. In search of adventure in my early 20s, I ended up at Lewa Downs Wildlife Conservancy in Kenya, a cattle station that had transformed itself into a wildlife conservancy, funding conservation and community through tourism. It changed the way I saw everything. The emotional connection between people, place, and moment at that African safari lodge was profound, and I came home to Australia convinced that we had all the same raw ingredients. The vast landscapes, the wildlife, the ancient culture, the characters on the land. What we didn’t have was anyone connecting those ingredients into deeply personal, emotionally rich journeys. That’s what The Tailor was founded to do – to prove that Australia could deliver travel experiences as powerful as anything I’d felt in East Africa.

We don’t focus on volume, and we’re not interested in luxury for the sake of luxury. A shared sunset or a genuine connection with a local host or guide is more powerful than any thread count. Our journeys are about privileged access – experiences that money alone can’t buy, built on decades of relationships and trust. We connect guests with extraordinary people: guides, hosts, conservationists, chefs – the people who give meaning to a place rather than just showing it.

What’s the entry level to talk to you?

Our trips typically start from around USD $1,500 per person. We begin with an initial conversation, by phone or email, to understand the client and what they’re looking for. From there, we provide a tailored itinerary outline with indicative pricing.

What is the sweet spot of your expertise?

The sweet spot is knowing where Australia’s most powerful stories live, and having the relationships to unlock them. Australia is an enormous, complex country, and the magic is almost never on the main road or in the obvious places. It’s in a private wildlife sanctuary where a fourth-generation rancher walks you across the same land his family has cared for over a century. It’s swimming with wild sea lions on a remote bay on the Eyre Peninsula, or sitting with an Aboriginal elder hearing Dreamtime stories at a coastal site most Australians don’t even know exists.

Our sweet spot is connecting those moments into a single, cohesive journey that feels effortless, even when it spans thousands of kilometres of remote and regional Australia. We’re especially strong in the places that are hard to get right: the Kimberley, the Top End of the Northern Territory, Tasmania’s wilderness, Tropical North Queensland, the Great Barrier Reef’s outer reef, and South Australia’s dramatic coastlines and wine regions.

We have a “little black book” of contacts – station owners, field guides, pilots, chefs, artists – and we know exactly who to call and when. The guides we work with embody a deep love for this country and a belief that true connection is defined by human interaction, not material things.

Ultimately, the sweet spot is in the customisation. We don’t sell pre-set packages. Every journey is hand-stitched. We listen deeply to what a guest actually wants – not what they think they want – and then we shape something that surprises them. We act as a “market-maker,” imagining what doesn’t yet exist and delivering it with detail and purpose. The goal is that our guests don’t just see Australia – they feel it, and they carry those stories for the rest of their lives.

A few favorite experiences/trips/itineraries you’ve planned that best represent your philosophy… 

This is a journey I recommend time and time again, especially for first-time visitors who want to experience the real Australia without the overwhelm. We’ve learned over 27 years that the secret isn’t trying to see everything, it’s choosing the right destinations and going deep. This itinerary brings together Australia’s most compelling experiences: the iconic harbour city, world-class wildlife encounters, ancient rainforest, and the Great Barrier Reef at its most pristine.

We start with three nights in Sydney at Capella, with a full day exploring the harbour and city, a private Opera House tour that takes you behind the scenes into spaces most visitors never see, and the Bridge Climb for that iconic perspective over one of the world’s most beautiful harbours.

From there, we head to Kangaroo Island – three nights at Southern Ocean Lodge, perched on the cliffs above the Southern Ocean. A full day of island life touring introduces you to wild koalas, sea lions basking on pristine beaches, and some of the most dramatic coastal scenery in Australia. The lodge itself is a masterpiece – floor-to-ceiling glass framing the ocean, locally sourced food, and a sense of total seclusion.

We pause for a night or two in Adelaide at Sequoia Lodge before a day tour through the Barossa Valley – one of Australia’s greatest wine regions, where you’ll taste exceptional Shiraz and meet the winemakers who’ve been working these vineyards for generations.

Next, two nights at Silky Oaks Lodge in the Daintree Rainforest, the world’s oldest living rainforest, where the jungle meets the reef. It’s lush, tropical, and utterly different from everything that’s come before.

We finish with four nights on Lizard Island, a secluded resort on the outer Great Barrier Reef. You’ll snorkel directly off the beach into some of the most pristine coral gardens on earth, explore private coves, dive the famous Cod Hole, and fall asleep to the sound of waves with nothing but the Coral Sea between you and the horizon.

Fourteen nights. Five destinations. Perfectly paced. And it never gets old, because the guides, the hosts, and the small moments are never the same twice. This is the journey that consistently earns us “best trip we’ve ever taken,” not because it’s extreme or over the top, but because it’s Australia at its finest – the icons done right, with depth, care, and genuine connection to place.

I also have two over-the-top trips that we’ve planned over the years that are some of my absolute favourites.

The first is one of my personal favourites, partly because I’m an avid fisherman myself, but mostly because it represents everything we believe in at The Tailor – privileged access, extraordinary people, and experiences that money alone simply can’t buy.

We designed this for a small group of serious anglers who wanted the ultimate Australian fishing experience. The concept was a superyacht as a floating hotel in the remote Gulf of Carpentaria – one of the most pristine and inaccessible fishing grounds in the world. But what made it special was the level of personalisation: each guest had their own private guide and boat, so they could fish at their own pace and target their own species. We also positioned a support vessel with a helipad to coordinate logistics and enable helicopter barramundi fishing with Dennis “Brazakka” Wallace, a legend in the IGFA Hall of Fame and a pioneer of heli-fishing in Australia’s Top End.

The fishing itself was world-class, but the final night is what elevated it into something unforgettable. We transformed the yacht with a smoking ceremony and Aboriginal dancers, flew in tropical blooms, and brought in an award-winning chef to prepare a banquet of Australian bush foods and fresh seafood caught throughout the week. As a parting gift, each guest received a rare barramundi bark painting sourced from Arnhem Land, wrapped in barramundi skin leather with personalised calligraphy tags.

It’s the kind of journey that requires years of relationships, deep local knowledge, and the ability to coordinate dozens of moving parts across one of the most remote regions on earth. And it’s exactly the kind of challenge that makes this work so rewarding.

Another one of my favourite trips was one that I planned with our Travel Designer Janelle, which connected far-flung destinations seamlessly using a Pilatus PC12.

This was a multi-week Australian adventure that took guests across some of the most remote and spectacular parts of the country without ever having to deal with commercial airports, security lines, or rigid schedules. The Pilatus PC12 became their private air safari vehicle – landing on remote airstrips from the Top End to Tasmania, the Red Centre to Kangaroo Island, wherever the journey took them. It was pure freedom.

What made this special was the way Janelle choreographed the entire flow. Each day, they’d wake up in one extraordinary location, spend time exploring with private guides, then simply walk to a nearby airstrip where their plane and pilot would be waiting to whisk them to the next destination. No rushing, no stress, no wasted time in transit terminals. The aircraft became a seamless extension of the journey itself – part logistics, part experience. Flying low over the Flinders Ranges at sunset, or island-hopping along the Great Barrier Reef, or landing on a remote station airstrip in the Kimberley – these weren’t just transfers, they were some of the most memorable moments of the trip.

It’s the kind of itinerary that requires not just budget, but imagination and a willingness to let go of conventional travel structures. And it’s exactly the kind of challenge we love, turning logistics into theatre, and making the journey between destinations as compelling as the destinations themselves.

Favorite hotels/lodges/houses you love and go back to again and again…

I have three stand outs, and they’re all places where the people and the land are inseparable from the experience.

True North – This is a 50-metre expedition vessel that’s been navigating Australia’s Kimberley coast for over 35 years. It carries just 36 guests, 22 crew, six expedition boats, and its own helicopter, which means you can access places that are genuinely unreachable any other way. Remote gorges, ancient rock art galleries, waterfalls, tidal rivers with a 2.2-metre draft that takes you into shallow waterways where larger ships simply can’t go. What I love about True North is that it’s active and immersive – early mornings, late nights, every day a genuine expedition. The service is authentically Australian – excellent service delivered with humour, equality, and mutual respect. There’s nothing pretentious about it. It’s the Kimberley the way it should be experienced.

Haggerstone Island – This is akin to Robinson Crusoe. A private island near Australia’s northern tip, accessible only by private charter – light aircraft to a nearby island, then a short boat ride across. Hosts Sam and Anna run it with a deeply personal touch. There are just five open-plan bungalows, and you can buy out the entire island for your group. The activities are extraordinary – fishing, spearfishing, snorkelling and diving the reef and WWII plane wrecks, exploring a neighbouring green turtle rookery by helicopter. It’s remote, it’s adventurous, and it’s one of the most genuinely exciting destinations in our portfolio. Every time I go back, I’m reminded that this is what real travel feels like – no agenda, no schedule, just the reef, the island, and whatever the day brings.

Bullo River Station – A 400,000-acre working cattle station in the Northern Territory, right near the Western Australian border, straddling the Bullo and Victoria Rivers. It takes just 12 rooms, and the atmosphere is like visiting a friend’s home, not a hotel. You wake up on the verandah overlooking tropical gardens, spend the day exploring gorges and waterfalls, viewing significant Aboriginal rock art, or fishing for barramundi in tidal river systems, and then sit down to a communal dinner of station beef and fresh barra. It’s a landscape of gorges, waterfalls, and tidal rivers, with 2,500 Brahman-cross cattle, buffalo, saltwater crocodiles, and incredible birdlife all around you. It’s the real outback, unfiltered.

The most memorable meal(s) you’ve had while traveling…

It was at Baird Bay, on the west coast of South Australia’s Eyre Peninsula, one of the most remote and beautiful stretches of coastline in the country. This isn’t a traditional restaurant, and you won’t find it on any foodie it-list. It’s a small, intimate coastal retreat on the edge of a 3,800-hectare shallow bay, and their chef is Calvin Von Niebel – a South African who spent over a decade at the high end of London’s dining scene working with Yotam Ottolenghi before finding his way to this wild corner of Australia.

The evening I’m thinking of, Calvin was cooking over an open fire directly on the beach. Sand beneath your toes. The sun slowly setting over the bay, turning the water gold, then pink, then deep violet. No shoes, no walls, no menu, just Calvin working the coals with quiet precision. Australian salmon barbecued over open flame. Blue swimmer crab, sweetcorn and herb fritters and a crunchy salad mixed with coastal greens. Plus Streaky Bay oysters with his homemade oyster sauce. And as the last light faded, the fire started speaking louder, and the stars – the kind of stars you only see when you’re hundreds of kilometres from the nearest city – started appearing one by one until the entire sky was blazing.

There was no one else on the beach. No noise except the fire, the bay, and the occasional conversation. It was the kind of meal where the food was extraordinary, but it was everything surrounding it – the remoteness, the intimacy, the elemental simplicity of fire and sea and sky – that made it unforgettable. That meal stays with me as a reminder that the most powerful dining experiences aren’t about Michelin stars or white tablecloths. They’re about place, people, and presence.

A few not-to-be-missed favorite experiences in your region(s) of expertise…

A privately guided journey through Arnhem Land. This is Australia’s deepest Indigenous cultural experience. Whether it’s a Yolngu Cultural immersion at Bawaka Homeland on the Gove Peninsula – where you live alongside the Burarrwaŋa family, participating in ceremony, spear-making, bush foods, weaving, and fireside storytelling – or a day at the rock art galleries of Mount Borradaile with a culturally credentialed guide, Arnhem Land offers encounters with living culture that are profoundly moving. These experiences require permits, careful planning, and the right guide, but when it all comes together, it’s transformative.

A private yacht on the northern Great Barrier Reef. Forget the day-trip crowds. The way to experience the reef is from a private vessel, anchored at the reef’s edge with nothing but ocean in every direction. Vessels like Aroona – a 21-metre motor yacht captained by Ross Miller, who has spent a lifetime on the Great Barrier Reef – take just six guests into the northern reef system, accessing spots within five metres of the reef edge thanks to a specially modified shallow draft. You dive, you snorkel, you fish, you kitesurf, and at the end of the day you sit on the aft deck with a glass of wine watching the sun drop into the Coral Sea. It’s the reef at its most intimate and powerful.

The Eyre Peninsula of South Australia – all of it. This is one of Australia’s most underappreciated stretches of coastline. Start with Coffin Bay, where you can shuck oysters straight from the water with a local. Head to Port Lincoln’s Mikkira Station to walk among wild koalas in their natural habitat, some only an arm’s length away. Then drive north-west to Baird Bay, where you swim with wild Australian sea lions and bottlenose dolphins in a protected bay. And from there, push inland to the Gawler Ranges – red sand, rocky gorges, three species of kangaroo roaming together, over a hundred bird species, and Lake Gairdner, a massive salt lake, glistening on the horizon, all explored from a safari camp in the mallee wilderness.

Underrated location, overrated location, personal favorite, recent discovery?

Underrated  – The Flinders Ranges, South Australia. I think the Flinders Ranges is incredible and hugely underrated. It’s only about four hours north of Adelaide, but it feels like another world – 600 million years of geological history laid bare in a landscape of ancient ridgelines, vast rock amphitheatres, and red-earth valleys. You can stay at the Prairie Hotel in Parachilna, a family-owned outback icon where the Gallery Restaurant is famous for “feral” and native flavours, and there’s even an on-site brewery – South Australia’s most remote. From there, you can arrange a private tour of the Nilpena Ediacaran fossil fields, walking across land where the first complex lifeforms on Earth emerged, exploring textured rock layers shaped over billions of years. The guides are outstanding, the landscape is primordial, and the sense of deep time is overwhelming. Most international visitors have never heard of it, which is part of what makes it so special.

Overrated – I don’t think any destination is truly overrated, what’s overrated is the way some popular destinations are experienced. Australia’s icons – the Great Barrier Reef, Uluru, Sydney Harbour – are iconic for a reason. They’re extraordinary. But the way they are sometimes visited often strips out everything that makes them powerful. You arrive on a crowded day trip, you tick the box, you take the photo, and you leave without ever really connecting to the place.

What we do differently is strip back the noise and build in the depth. Take Sydney – most visitors see the Opera House from the outside, do the standard bridge walk, eat at a restaurant someone found on a list, and move on. We take our guests inside the Opera House on a private tour of spaces not generally open to the public, guided walks through the Sydney Botanic Gardens with an Eora Nation Elder and then – through relationships we’ve built over decades – open doors that simply aren’t available to the general public. That might mean being taken via a secure elevator to a private pearl grading room where master craftsmen are creating pearl strands that take up to 18 years to produce. Or a day in the Blue Mountains with James Castrission, one of Australia’s 50 greatest explorers, abseiling into untouched slot canyons that feel like time capsules. Same city, completely different experience.

So my answer to “overrated” is really this: no destination is overrated if you experience it with the right people, at the right pace, and with genuine access to the story beneath the surface. The problem is never the place, it’s the approach.

Personal Favourite – That’s a hard one, I have two.

Mt Borradaile, Arnhem Land – I did this as part of a larger private 4WD trip with an amazing guide, and the natural history and rock art at Mt Borradaile is unsurpassed. It’s located on an exclusive 700-square-kilometre lease in north-west Arnhem Land – a registered Aboriginal sacred site entrusted to a select few operators by the Traditional Custodians. One such guide, David McMahon, Head Tour Guide for Venture North is extraordinary – his knowledge and his relationships with the Traditional Owners make the experience authentic in a way that few cultural encounters anywhere in the world can match. The rock art is in the Arnhem Land X-ray style, distinct from the Gwion Gwion and Wandjina art of the Kimberley, and the galleries are vast, layered, and awe inspiring. It was one of the most incredible days I’ve had in nearly 28 years of doing this.

Helicopter Safari from Cairns to the tip of Cape York – Another favourite personal trip was seven days spent in a Robinson R44 helicopter with a private guide, flying from Cairns all the way to the Torres Strait Islands at Australia’s north-eastern tip. We fished remote rivers and estuaries for barramundi along Princess Charlotte Bay – one of the most remote and productive fishing grounds in the country, where we even spotted dugong. We stayed at Haggerstone Island with Roy and Anna, explored WWII plane wrecks scattered across Cape York, island-hopped through the Torres Strait, and experienced Indigenous cultures that most Australians don’t even know exist. It’s the kind of trip that reminds you why you got into this work in the first place.

Recent Discovery – Kimberley Spirit, on the Ord River in the East Kimberley. It’s run by Scotty and Taminga – Scotty has more than 20 years guiding in the Kimberley, and Taminga is from the Bunuba Gija clan and is an accomplished Aboriginal artist. They’re one of those rare operators where the hosts are the experience. About half their business is repeat guests and personal referrals, which tells you everything.

Their centrepiece is the Ngarwan – “the Gathering” – a 16-metre solar-powered houseboat on the Ord River, exclusively chartered for up to six guests. It’s fully off-grid, floating through some of the most dramatic river gorge scenery in Australia. One guest described it as “the Grand Canyon with no people.” There’s a fast boat for exploring the wider river system, a helipad at their property base for helicopter days, and 4WD touring through gorges and remote country when you step off the water.

What sets them apart is how they host. They call it “read the play” – adjusting the itinerary in real time based on their guests’ energy and mood, building in experiences they don’t advertise to protect the places and the exclusivity. Taminga’s food and hospitality rival high-end cruise vessels, but the setting is a quiet stretch of the Ord surrounded by birdlife, freshwater crocodiles, and ancient rock. Scotty’s cultural storytelling – sharing Bunuba Gija stories and deep country knowledge – is genuine, not performative. They also operate through the wet season when most of the Kimberley shuts down, which transforms everything – waterfalls everywhere, everything lush, and you have it entirely to yourself. It’s going to become one of the most compelling private experiences in the Kimberley.

The hardest-working item you always pack…

A steam iron. I know – not exactly what you’d expect from a kid that grew up on a rural property. But here’s the thing: I spend a lot of my time visiting our suppliers, meeting partners, hosting guests, and representing The Tailor in all kinds of settings – from remote station homesteads to city boardrooms. When you step off a small charter plane or pull up to a lodge after a long drive, turning up looking sharp says something. It says you care about the details. And details are what we do. A steam iron is the one item that consistently earns its place in my bag because it lets me show up the way I want to – polished, considered, and ready, no matter how remote the destination. It’s a small thing, but the small things matter.

What is something you wished we all knew or were better at as travelers?

Slow down. Genuinely, meaningfully slow down.

I’ve spent 27 years watching travellers try to see everything, and the irony is that the more you try to fit in, the less you actually experience. You end up with a highlight reel of places you passed through rather than a collection of moments that changed you. The instinct is always to add more – one more destination, one more stop, one more experience. But the truth is, less is more. And more – real, unhurried, deeply felt more – only happens when you give yourself permission to stay.

Stay the extra night. Take the slow road. Say yes to the unplanned afternoon. Some of the most extraordinary moments I’ve seen on our journeys weren’t on any itinerary – they were the campfire conversation that went late, the second morning walk where the guide finally shows you the thing he’s been waiting to reveal, the afternoon where nothing was “on” and a family just sat together on a beach in silence, watching the light change. That’s where travel becomes something you carry with you forever.

Australia rewards patience like almost no other destination on earth. The distances are vast, the landscapes shift slowly, and the best experiences – whether it’s an Aboriginal elder sharing a story or hundreds of brightly coloured parrots streaking across the sky – happen on their own time, not yours. The travellers who come to us and say “I just want to go deep” – they’re the ones who leave transformed. So, if I could wish one thing for all of us, it would be this: resist the urge to see it all, and instead, feel where you are. That’s where the real travel lives.