A Classic Drive Through a Modern Australia
An expertly curated self-drive discovering Australia’s most breathtaking scenic routes with memorable stops.
Day 1 - Sydney to the Southern Highlands
- Sydney
- Royal National Park
- Austinmer Beach
- Picton
- Berida Hotel, Bowral
Trade the crowds for coastal curves and forest stillness. This opening day is defined by handpicked roads south of Sydney, chosen for their beauty, sense of space, and memorable driving.
Begin with a private hotel pick-up and transfer to the vehicles, followed by a tour briefing before setting out. The drive follows the shores of Botany Bay, where Captain Cook first set foot in Australia in 1770, before continuing through the Royal National Park, the world’s second-oldest national park after Yellowstone.
Climb toward Stanwell Tops for sweeping coastal views, then continue along the New South Wales South Coast with a stop at Austinmer Beach. The route then rises through the escarpment, passing historic towns and elevated lookouts on the way to the Southern Highlands.
Arrive in Bowral and check in to the heritage Berida Hotel for your first night. Dinner is included at Bistro Sociale, offering a relaxed and refined end to the day.
Day 2 - Coastal Delights & Highland Vistas
- Berida Hotel, Bowral
- Shoalhaven Seafood
- Fitzroy Falls
- Berida Hotel, Bowral
Following breakfast, depart the hotel for a spectacular drive back toward the coast via Jamberoo Mountain Road. Continue south to the oyster and shrimp/prawn harvesting areas of Shoalhaven Heads, where time is set aside to sample local seafood delicacies during lunch.
The journey continues through the pass known as Kangaroo Valley, a rewarding drive offering both challenge and safety, before stopping at Fitzroy Falls to admire the escarpment views. Return to Berida Hotel in Bowral for the second night. Dinner is included.
Day 3 - Illawarra Escarpment to Sydney
- Berida Hotel, Bowral
- Shellharbour Aircraft Museum
- Illawarra Escarpment
- Sydney Hotel
- Harbour Cruise
After breakfast, depart the hotel for the drive back to Sydney, passing through the lush rainforest of Macquarie Pass. A leisurely stop at the Shellharbour Aircraft Museum offers a glimpse into Australia’s aviation heritage.
Continue along the Illawarra Escarpment, stopping in Bulli for lunch and at the Panorama Lookout for sweeping views of Wollongong, New South Wales’ largest southern coastal city. Arrive at the Shangri-La Hotel, your five-star Sydney accommodation overlooking the harbour, and prepare for a Sydney Harbour cruise featuring a four-course dinner against the city’s iconic skyline.
Day 4 - Historic Sydney & Harbour Farewell
- Shangri La Hotel
- The Rocks Historic Walk
- Watsons Bay Waterfront Lunch
Start the morning with a guided walk through The Rocks, Sydney’s historic birthplace, where your guide will share the stories behind the cobbled lanes and sandstone buildings.
Late morning, your cars await for the drive to Doyle’s Seafood Restaurant at Dreamy Watsons Bay, where a three-course lunch is served with views back across the harbour. Return to the original meeting point via the city’s underground road tunnels, and a private transfer completes the journey back to your hotel.
Credit: Destination NSW
Inclusions
- Drive the Silver Arrow Classic Mercedes-Benz SL350 (R230) for approximately 550 km over four days, with fuel and comprehensive insurance included so you can focus purely on the driving experience.
- Return transfers between your hotel and The Bakehouse Quarter, ensuring a smooth and hassle-free start and finish to your journey.
- Two nights of accommodation at the Berida Hotel in Bowral, NSW, including breakfast and a three-course dinner to unwind after a day on the road.
- One night of luxury accommodation at the Shangri-La Hotel Sydney, including breakfast with stunning views of the harbour.
- A privately guided scenic drive from Sydney to the South Coast and the Southern Highlands, before returning to Sydney — designed to showcase some of the region’s most beautiful roads and landscapes.
- Admission fees and guided tours included, so you can enjoy each destination without worrying about additional arrangements.
- A sunset Sydney Harbour cruise with a four-course dinner, offering spectacular harbour views as the city lights come alive.
- A three-course lunch at Doyle’s Watson’s Bay, one of Sydney’s most iconic waterfront dining destinations.
- Detailed trip notes to guide you through each stage of the journey.
- An interactive Google Maps route guide, helping you stay on track and fully enjoy every part of your driving adventure.
Pricing
A$6,750
Per person, in double room · GST included
An all-inclusive four-day driving experience featuring luxury accommodation, curated dining, guided scenic routes, and the thrill of driving a Silver Arrow Classic Mercedes-Benz.
Next Tour Dates
Don’t just see the sights – experience them. Every route has been driven, loved and refined.
This is the road trip you’d design if you had all the time in the world.
FAQ
Yes, this is a guided self-drive tour. Typically we will operate with four to six cars in the group (eight to twelve guests). You will be driving your allocated car, however, there will be a lead car showing the way for the group so there is little chance of losing your way.
The following items are not included in the tour price:
Travel and flight costs to and from Sydney, Australia
Meals other than those specified in the itinerary
Alcoholic beverages
Personal medication
Travel insurance (this is the guest’s responsibility and required to recover any personal loss)
Insurance for personal items such as phones, tablets, and other valuables
Accommodation costs before the tour begins and after the tour ends
Yes, you must be at least 30 years of age.
No, as long as you have a valid driver’s licence from your country you can drive in Australia. However, if the licence is not in English it will need to be translated or you will need an International Driving Permit (IDP).
We will arrange to pick you up from your Sydney Hotel, and at the end of the four day tour we will arrange to transfer you back to your Sydney Hotel.
You will be spending much of the day driving, so wear comfortable casual clothes and comfortable shoes. A warm jacket for roof down driving may also be advisable depending on the season.
Australian society is very casual, so smart casual wear is fine for the evenings.
We understand you may well be in Australia for much longer than the four days of this particular tour, so you and your partner may have larger suitcases. However, keep in mind these are sports cars with limited trunk space, so we suggest you store the larger suitcases and only bring an ‘airline carry-on’ sized suitcase and a soft bag each for the three nights of this tour.
No, we cover the cost of fuel each day and we also cover all the highway toll charges for the four days.
Most countries drive on the right hand side of the road. In Australia, and all former British colonies, we drive on the left hand side of the road. However, this does not take long to get used to, indeed, the only time there could be room for confusion is at a T Junction or at a Roundabout. For this reason we have a lead car showing you the way and taking the stress out of driving on foreign roads.