Experience laid-back luxury and form deep connections with Australia's people, landscapes, and wildlife with this deluxe two-week trip. Starting in Sydney, tick off the icons and cycle the city before landing in Hobart for a self-drive Tasmanian adventure to historic Port Arthur and the breathtaking Freycinet National Park. After, skip over to Kangaroo Island, where another 5-star nature lodge awaits. Finish in charming Adelaide with walking tours and wine tastings.


  • Stay in luxurious 5-star hotels and exclusive nature lodges
  • See Sydney's iconic sights with a private sunset dinner cruise
  • Road trip across Tasmania to historic Port Arthur and Freycinet National Park
  • Connect with nature and wildlife on Kangaroo Island
  • Sip rich juicy red wines on a full-day private Barossa Valley tour

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Sydney, Sunset Dinner Cruise Sydney
Day 2 Full-Day Wildlife in the Wild Tour Sydney
Day 3 Welcome to Country Ceremony, Guided Bike Tour, Opera House Experience Sydney
Day 4 Fly to Hobart, Visit MONA, Guided City Walk Hobart
Day 5 Full-Day Tasmania Wilderness & Wildlife Tour Hobart
Day 6 Pick Up Rental Car, Drive to Port Arthur, Wilderness Cruise Port Arthur
Day 7 Drive to Freycinet National Park, Wineglass Bay Lookout Walk Freycinet
Day 8 Wineglass Bay Cruise, Optional Activities Freycinet
Day 9 Drive to Hobart, Fly to Adelaide, Evening Wine, Dine & Discover Walk Adelaide
Day 10 Fly to Kangaroo Island, Kangaroo Island in Style (Day 1) Kangaroo Island
Day 11 Kangaroo Island in Style (Day 2) Kangaroo Island
Day 12 Fly to Adelaide, Essence of Adelaide Tour Adelaide
Day 13 Full-Day Barossa Valley Wine Tour Adelaide
Day 14 Depart Adelaide  

Detailed Itinerary

Day 1: Arrive in Sydney, Sunset Dinner Cruise

Welcome to Sydney
Catch harbor views from the poolside at your 5-star Sydney hotel (photo courtesy of Crown Towers)

Say g'day to wonderful Sydney! This Australian city is a must-visit destination for good reason. With a dazzling natural harbor, epic beachside walks (not to mention beaches), a world-class restaurant and bar scene, excellent live music and theater, and an unquenchable thirst for fun, you'll never get bored in this city. A private driver will transfer you from the airport to your hotel, the 5-star Crown Towers. The sculptural hotel resembles three twisting petals reaching skyward, giving every luxe room exquisite views of Sydney from its position at Barangaroo.

Settle in, then set out to explore Sydney's neighborhoods and beaches. Catch a glimpse of local life in trendy Surrey Hills or hipster Newtown, then venture out to Bondi Beach to watch the surfers. You could take a lesson yourself or wander the waterfront Bondi to Bronte coastal walk. Return to the center and step aboard a 52-foot (16 m) motor yacht for a four-hour deluxe dinner cruise on Sydney Harbour, where you'll watch day turn to night as you feast on a delicious Australian barbecue dinner and learn about the city as you pass famous landmarks.

Day 2: Full-Day Wildlife in the Wild Tour

Full Day Private Wildlife in the Wild Tour
See wallabies and kangaroos in the wild with today's all-day private tour

Experience Australia's native bushland and seek out iconic native animals in their natural habitat with today's full-day private wildlife tour. A guide and driver will take you to a private property in the Southern Highlands, just 90 minutes south of Sydney. Here, you'll wander through towering forests of grey gums in search of koalas, look for platypus along the riverbanks, and drive through woodlands as mobs of kangaroos feed. Look for wallabies and the elusive emu while your guide describes the birdlife and bushland.

After dinner, you'll go night spotting for nocturnal wombats, gliders, and possums, which are most active in the evening. After a full day immersed in nature, you'll return to your luxurious digs in the center of Sydney.

Day 3: Welcome to Country Ceremony, Guided Bike Tour, Opera House Experience

Sydney Opera House
Did you know the Sydney Opera House hosts more than 2,000 shows every year?

This morning, connect with the Aboriginal culture of Australia's traditional owners. Discover Sydney's Dreamtime identity with a private Welcome to Country ceremony. You'll experience a traditional white ocher scenting from Earth Mother or a mini smoking ceremony while learning about the origins, purpose, and relevance to modern Aboriginal people. After, explore the sights of Sydney with a private bike tour. Pedal past Circular Quay, the Royal Botanic Gardens, the piers at Walsh Bay, Darling Harbour, Chinatown, and Hyde Park with a local guide who will share tales of the city.

This afternoon, prepare to peek beneath the sails of a 20th-century architectural masterpiece, the famous Sydney Opera House. With its sleek vaulted shells, this expressionist marvel is a testament to human imagination and was the brainchild of Danish architect Jørn Utzon. Today, you'll step inside this global icon, UNESCO World Heritage Site, and performing arts venue to see its inner workings. Learn about the history of the Opera House and its design elements as your private guide shares entertaining stories and takes you to off-limit areas. After, grab a drink at the waterfront Opera Bar.

Day 4: Fly to Hobart, Visit MONA, Guided City Walk

Expansive views over the Derwent River from your modern treetop escape (photo courtesy of Mona Pavilions)

After breakfast, a private drive will transfer you to Sydney airport for your domestic flight to Tasmania. The triangular island state at the bottom of Australia is steeped in history, with wild and beautiful landscapes, friendly people, and a temperate climate. Its capital, Hobart / nipaluna, sits at the foothills of Mount Wellington / kunanyi and combines heritage charm with a relaxed modern lifestyle. On arrival, a private driver will take you to the artsy Mona Pavilions, a slick luxury hotel set on a private peninsula of the Derwent River.

Your suite, aptly named after an Australian artist, is part of MONA, a bucket-list, world-class gallery. Tasmania's remarkable Museum of Old and New Art uses art to shock, inspire awe, and make you laugh. It's best to visit with an open mind, curiosity, and a sense of wonder. Use your afternoon to explore the immersive and unique gallery, then take the gallery's quirky ferry into town.

This afternoon, you'll get to know Tasmania's capital inside out with a private walking tour. On foot, you'll discover the city center, Salamanca, and Battery Point. Your local guide will identify the heritage-listed buildings and tell the stories of the early characters and issues that were significant influences in the city's early days. After the tour, find dinner in town or go visit a local bar to taste some of Tasmania's famous single malt whiskey.

Day 5: Full-Day Tasmania Wilderness & Wildlife Tour

Full Day Private Tasmania's Wilderness & Wildlife
Tasmanian devils have 42 teeth, like a dog, but they keep growing throughout its life

An island cut from the mainland, Tasmania is home to a unique range of Australian wildlife, with many critters and creatures not found beyond the island state. Today's full-day private tour will take you to Bonorong Wildlife Sanctuary to meet Tasmanian devils, wombats, quolls, and other Australian animals. You'll be able to hand feed kangaroos and feel good knowing your visit supports a dedicated team of wildlife carers who research and care for native wildlife in Tasmania.

Your journey continues through the picturesque Derwent Valley, dotted with orchards, hops fields, and quaint reminders of the historic origins of the area. After a local lunch, you'll journey to Mount Field National Park, the oldest national park in the state and one of the most diverse. Explore the green forest canopy and crane your neck to see some of the tallest flowering trees and eucalypts in the world. Take a short walk through the lush rainforest to reach the cascading three-tiered Russell Falls before returning to the city.

Day 6: Pick Up Rental Car, Drive to Port Arthur, Wilderness Cruise

Port Arthur
Port Arthur was first established in 1830 as a timber-getting camp
Plan your trip to Australia
Chat with a local specialist who can help organize your trip.

It's time to embark on your Tassie road trip! After breakfast, pick up a rental car and drive to the historic village of Port Arthur. The 19th-century penal settlement is now an open-air museum and a dramatic reminder of Australia's convict past. Australia's most intact and evocative convict site has over 30 buildings, ruins, and restored period homes set in 98 acres (40 ha) of landscaped grounds. Highlights include the ruins of the huge penitentiary and the remaining shell of the Convict Church, originally built by inmates. 

Change pace next with a three-hour wilderness cruise. Aboard a small, high-speed vessel, you'll zip past dramatic coastal cliffs and rock formations on the open eastern side of the peninsula, taking in the coastline between Port Arthur and Eaglehawk Neck. You'll squeeze beneath the highest vertical sea cliffs in the Southern Hemisphere at Cape Pillar and see the waterfalls, rock formations, archways, and deep-sea caves of Tasman National Park. Keep your eyes peeled for a variety of wildlife, including seals, migrating whales, playful dolphins, and abundant sea birds in their thousands.

Finally, go and check into your own private chalet at Stewarts Bay Lodge, a stunning property set on 22 acres (9 ha) between Tasmanian beach, forest, and Port Arthur. 

Day 7: Drive to Freycinet National Park, Wineglass Bay Lookout Walk

Check into luxury in the heart of Freycinet National Park (photo courtesy of Saffire Lodge)

Today's road trip takes you north to Freycinet National Park, a three-hour drive. If time permits, stop off in Triabunna for a self-guided architecture walk or stroll the Pelican's Walk. Continue on the road and into the park. The two-hour walk to Wineglass Bay Lookout is considered one of the Great Short Walks of Tasmania. From the top, you'll be rewarded with one of the island's most celebrated views over the beautiful white sands of Wineglass Bay and Freycinet National Park.

From up here, you have a choice: hike down to Wineglass Bay Beach, a 2.5-hour return trip, or explore other sights in Freycinet National Park. If you venture down to the beach, you'll find pristine white sands and a chilly ocean. If you prefer less walking, you could cruise over to Honeymoon Bay, Cape Tourville Lighthouse, and Sleepy Bay Lookout. When you're ready, drive over to the all-inclusive Saffire Lodge, one of Australia's most remarkable stays. Check into the award-winning hotel and continue breathing in the landscapes of Freycinet National Park from your expansive luxury suite.

Day 8: Wineglass Bay Cruise, Optional Activities

Opt for an oyster experience at Freycinet Marine Farm this afternoon (photo courtesy of Saffire Lodge)

Leave the car behind—today, you'll experience the Freycinet Peninsula from the water. Board a 4.5-hour eco-cruise of Wineglass Bay, departing from Coles Bay. Pass the dramatic granite coastline, including the dramatic pink peaks of the Hazards range, one of Tasmania's most extraordinary places. Standing on the private upper deck of the Schouten Passage II, you'll spot wildlife, such as dolphins, seals, seabirds, and migrating whales, as you tuck into morning tea or your gourmet lunch platter with oysters, smoked meats, Tasmanian cheeses, salad, fruit, and bread. 

In the early afternoon, return to Saffire and soak up the luxury of your all-inclusive stay. Borrow kayaks and stand-up paddleboards to explore Freycinet, or organize an exclusive behind-the-scenes tasting at Freycinet Marine Farm. Picture yourself donning a pair of waders and stepping into the heart of a working oyster farm. In the middle of the bay, you'll taste freshly shucked oysters while learning about sustainable oyster farming.

Day 9: Drive to Hobart, Fly to Adelaide, Evening Wine, Dine & Discover Walk

Dive into Adelaide's back streets this evening for a tour of lesser-known local wine bars

After a slow final breakfast at Saffire, it's time to return to Hobart / nipaluna. Set off on the 2.5-hour drive, stopping at Sorell, one of Tasmania's oldest farming towns. Admire heritage buildings and pick your own fresh berries, stone fruits, or apples at Sorell Fruit Farm. Linger at the café for lunch before returning the rental car and catching your flight to Adelaide. The capital of South Australia is a small, progressive city that boasts great festivals, fine food, and world-class wine. On arrival, a private driver will collect you and your bags for a transfer to the heritage-listed 5-star Mayfair Hotel

Settle in, refresh, then set out this evening for a culinary walking tour. Start at one of the city's lesser-known local wine bars for an introduction to the region's best wines over snacks. Wander Adelaide's back streets, admiring the architecture, street art, and atmosphere on the way to the next location: a hidden bar to discover local spirits and creative cocktails. Hear about local laws and legends, the saints, sinners, innovators, and creators who have shaped this unique Australian city. Finish with a digestive and delicious fresh cheese or sweet treats at a local institution.

Day 10: Fly to Kangaroo Island, Kangaroo Island in Style (Day 1)

Your eco-resort blends seamlessly with its surroundings (photo courtesy of Southern Ocean Lodge)

Early this morning, a private driver will collect and transfer you to the airport, where you'll catch a quick 35-minute flight to Kangaroo Island, a favorite foodie and wildlife destination. Your private guide will meet you at the airport in Penneshaw, ready to show you the island's top sights. More than a third of the island's total area comprises protected wildlife reserves, and hopefully, you'll see the small wallabies almost extinct on the mainland and a kangaroo found only on this aptly named island. Start with a guided bush walk, where you'll learn about the fauna and flora of the island.

Break for lunch at a private bush camp to enjoy a delicious meal featuring King George whiting (local sea fish), fresh salads, and fine South Australian wines. Tour Seal Bay Conservation Park next to see Australian sea lions on a beautiful sandy beach. Watch pups nursing or playing in the surf, see old bulls with scars of territorial disputes, and learn about their unique breeding biology. In the late afternoon, you'll check into Southern Ocean Lodge, a resort celebrated globally as a pioneer in experiential luxury. Enjoy welcome drinks as the sun sets and settle into your deluxe room. 

Day 11: Kangaroo Island in Style (Day 2)

Kangaroo Island in Style (Day 2)
Remarkable Rocks have been shaped by 500 million years of wind, sea spray, and rain

Enjoy an immersive breakfast in this bush this morning before meeting your private guide for another full day of sightseeing. Today you'll travel through the island's northwest and visit Kangaroo Island Wildlife Park, an important private wildlife reserve. Learn about the programs for protecting endangered mammals and fire ecology, and feed local kangaroos before taking a break to enjoy an elegant picnic surrounded by nature. 

After, travel into Flinders Chase National Park and explore the massive shapes of Remarkable Rocks, a natural sculpture perched impossibly on top of a dome of granite emerging from the ocean. Evidence of the power of the Southern Ocean swell continues at Admirals Arch, a coastal grotto that provides shelter for a large colony of long-nosed fur seals who frequent the crashing waves. Back at the lodge, journey out to an architecturally designed viewing platform for sunset drinks and wait patiently as local wildlife venture out at dusk to graze.

Day 12: Fly to Adelaide, Essence of Adelaide Tour

Half Day Private The Essence of Adelaide
Adelaide is nicknamed the City of Churches and Australia's oldest cathedral is found here

Enjoy a slow breakfast at the lodge, sampling local goodies like free-range eggs, Ligurian honey from the island's hives, smoked salmon, cured meats, and lodge-made pastries. Breathe in your final moments of remote island life, then it's time to say goodbye to Kangaroo Island. A private transfer will take you back to the airport for your short return flight to Adelaide. On arrival, another private driver will take you back to the beautiful Mayfair Hotel.

Drop your bags off, then join a half-day private tour of the small southern city. Adelaide is actually one of the best-planned cities in the world, and you'll explore the grid-pattern center on foot while learning about its history and heritage. This private and personalized walking tour of the South Australian capital can be further customized to your interests.

Day 13: Full-Day Barossa Valley Wine Tour

Barossa Valley
The Barossa Valley is famous for its rich red wines and has more than 150 wineries and 80 cellar doors

The historic Barossa Valley might be Australia's best-known wine region, but today you'll explore its secrets. A private guide will take you to lesser-known boutique wineries that are big on character. You'll meet passionate locals, sample outstanding wines, and enjoy a tasting menu at one of the region's top restaurants. Over a full day of exploration, you'll taste the old and the new, the famous and the yet-to-be-discovered, with a tour itinerary flexible to your tastes.

After an epic day traipsing around the beautiful Barossa, you'll return to Adelaide for your final night in Australia. If you have the energy to hit the town, make a reservation at the very special Restaurant Botanic. Set within the 126-acre (51 ha) Adelaide Botanic Garden, this restaurant focuses on place and time, highlighting the micro-seasons of the garden and the day's weather. As a guest, you're invited to touch, taste, and experience the meal completely while also having a laugh. It's a luxe yet laid-back place—the kind that could only exist in Australia.

Day 14: Depart Adelaide

Depart Adelaide
Wave goodbye to the beautiful and green city of Adelaide and depart Australia
Your grand holiday in Australia concludes today. After two great weeks, it's time to zip up the suitcase for the final time and wait for your private driver in the lobby. Take a transfer to the airport in time for your homeward-bound flight. Safe travels!

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Map of Luxury Sydney, Tasmania & South Australia - 14 Days
Map of Luxury Sydney, Tasmania & South Australia - 14 Days