Sydney to South Coast Itinerary

Credit: Destination NSW

Day 1

  • Sydney
  • Royal National Park
  • Austinmer Beach
  • Picton
  • Berida Hotel, Bowral

Trade the crowds for coastal curves and forest stillness.
The itinerary is handpicked for beauty, solitude and unforgettable roads south of Sydney.
From sweeping sea cliffs to hidden vineyards, we guide the way – you set the pace.

Pick up from Hotel, Drive to cars, Tour Briefing, set out on the tour and drive along the shores of Botany Bay where Captain Cook first set foot in Australia in 1770. Drive through the Royal National Park (the 2nd oldest National Park in the world after Yellowstone) to Stanwell Tops. Continue along the New South Wales South Coast stopping at Austinmer Beach, then climb the Escarpment to amazing lookouts and Historic towns along the drive to the Southern Highlands and finally arriving at your accommodation, the Berida Hotel, for the first night. Dinner included at Bistro Sociale.

DAY 2

  • Berida Hotel, Bowral
  • Shoalhaven Seafood
  • Fitzroy Falls
  • Berida Hotel, Bowral

Following Breakfast, depart hotel for a spectacular drive back to the coast via Jamberoo Mountain Road and then head further south to the Oyster and shrimp/prawn harvesting areas of the Shoalhaven Heads to sample some of these delicacies during lunch. Next a challenging but safe drive through the pass known as Kangaroo Valley stopping at the Fitzroy Falls and return to the Berida Hotel for the second night. Dinner included.

Credit: Destination NSW

Day 3

  • Berida Hotel, Bowral
  • Shellharbour Aircraft Museum
  • Illawarra Escarpment
  • Sydney Hotel
  • Harbour Cruise

After Breakfast, depart the hotel for your return to Sydney via the rainforest of Maquarie Pass and a leisurely drive to visit the Shellharbour Aircraft Museum. Then proceed along the Illawarra escarpment stopping at Bulli for lunch and the Panorama lookout affording a view of Wollongong, New South Wales’ largest southern coastal city. Arrive at the Shangri-La Hotel your Sydney City 5 star accommodation overlooking the Harbour and prepare for your Sydney Harbour cruise and four course dinner.

DAY 4

  • Shangri La Hotel
  • The Rocks Historic Walk
  • Watsons Bay Waterfront Lunch

Your accommodation is situated in The Rocks area, the birth place of modern Sydney and we recommend a walking tour where a guide will explain the history of the area. Late morning and your cars will be waiting for you to drive to Doyle’s Seafood Restaurant on Dreamy Watson’s Bay for a three course meal and views back up the Harbour. Drive back through the underground tunnels of the city’s road infrastructure to our original meeting place from where  you will be driven back to your hotel.

Credit: Destination NSW

Inclusions

  • Transfer from hotel to and from The Bakehouse Quarter starting point.
  • You drive the Silver Arrow Classic Mercedes-Benz SL350 (R230) for 550kms over four days, including comprehensive insurance and fuel.
  • 2 nights accommodation including breakfast and a three course meal at the Berida Hotel in Bowral NSW.
  • 1 night accommodation, including Breakfast, at the Shangri La Hotel Sydney.
  • Privately guided drive from Sydney to the South Coast, the Southern Highlands and back to Sydney.
  • Admission fees and guided tours as per itinerary.
  • Sunset Sydney Harbour Cruise with 4 course dinner.
  • Three course lunch at Doyles Watson’s Bay.
  • Trip Notes.
  • Google Maps Interactive Route Map.

Pricing

  • Per person, in double room, incl. GST A$5,450

Next Tour Dates

Don’t just see the sights – feel 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.

27th to 30th January 2026 – Book Tour!

10th to 13th February 2026 – Book Tour!

24th to 27th February 2026 – Book Tour!

10th to 13th March 2026 – Book Tour!

31st March to 3rd April 2026 – Book Tour!

LIMITED AVAILABILITY

Not included

Travel to and from Sydney, Australia, meals other than as indicated and alcoholic beverages.

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.

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.