Sydney and Surrounds Road Trip Itinerary

Welcome to Sydney, the oldest and grandest of Australia's big cities. Dynamic, cosmopolitan and surrounded by stunning natural attractions, Sydney is the ultimate big city getaway. 

Set on one of the most beautiful harbours in the world and with famous architectural icons such as the Sydney Opera House and Sydney Harbour Bridge to explore, Sydney offers plenty of excitement at any time of the year.

Settle in with a stroll along Circular Quay. With the Harbour Bridge at one end and the Opera House at the other, is there any more iconic place to begin your Australian dream vacation?

Accommodation: Sydney - 3 Nights

Discover Sydney’s rich and complex story on this expert-led small-group walking tour. Explore key landmarks while gaining insight into Australian history, culture, society, and the experiences of First Nations people. 

Beginning at Customs House, learn about British colonisation and its impact on the Cadigal people of the Eora Nation. Along the way, hear stories of Aboriginal leaders, governors, convicts, entrepreneurs, and migrants who shaped the city. The tour winds through Sydney’s vibrant centre before concluding in The Rocks at a popular brewery, where harbour views of the Sydney Opera House and Harbour Bridge provide a memorable finishing touch.

Included Meals: Breakfast

Collect your rental car and take a leisurely drive to the famous Hunter Valley. Australia’s oldest wine region is home to a staggering 150 wineries, from the biggest names to tiny boutique growers. 

It’s only a 40-minute drive from one end of the Valley to the other so there's plenty of time to admire the region's sweeping landscapes: you're likely to encounter your first wild kangaroos here too.

Included Meals: Breakfast

Approximate Distance: 172km | 107 miles   Total Driving Time: 2 hours 30 mins

Accommodation: Hunter Valley - 2 Nights

Enjoy a self-guided tour of the onsite museum at Audrey Wilkinson Vineyard, followed by a master class and premium tasting from the in-house wine expert. 

Collect your bottle of handpicked wine along with a picnic hamper and select a scenic location within our 270 acre property to enjoy the picturesque view and immerse yourself among the vines where you will feel as though you have the whole vineyard to yourself!

Included Meals: Breakfast, Lunch

Port Stephens is called the "blue water paradise" because of the beauty of its marine surroundings. It is located about two and a half hours north of Sydney, on the East Coast of Australia, and has a population of about 50,000. 

With over 19 miles of clean, white, sandy beaches, Port Stephens boasts vibrant tourism and fishing industries. Port Stephens is home to around 165 bottlenose dolphins, which live in the Port itself. If you are lucky you can view them from the shore or hire a boat. Alternatively, join a tour that takes you around the Port dolphin watching.

Included Meals: Breakfast

Approximate Distance: 115 km | 71 miles   Total Driving Time: 1 hour 30 mins

Accommodation: Port Stephens - 2 Nights

Guests are invited to snorkel with Irukandji’s impressive three metre tawny nurse sharks and the lively whitetip reef sharks in a thrilling yet carefully managed encounter. 

This fully immersive experience provides rare access to the big shark zone of the Tropical Lagoon, guided by a private instructor who ensures comfort and confidence throughout the adventure. Snorkelers glide through clear water as the sharks cruise calmly nearby, creating an unforgettable sense of connection with these remarkable animals. It is an exhilarating and safe opportunity that delivers incredible photos and the proud moment of saying I swam with sharks in Australia.

Prepare to be awed by rugged sandstone cliffs, hidden canyons, towering waterfalls and never-ending expanses of gorgeous eucalyptus forests. The World-Heritage-Listed Blue Mountains region is guaranteed to impress.

Outdoor-lovers will delight in 140 kilometres (87 miles) of walking tracks, surrounded by native bushland and the blue haze which gives the region its name.

Approximate Distance: 305 km | 190 miles   Total Driving Time: 3 hours 30 mins

Accommodation: Blue Mountains - 3 Nights

With a blue horizon of eucalyptus trees that appear to stretch on forever, expect to be enchanted by the natural beauty of the Blue Mountains World Heritage Area. 

Set out on foot to explore some of the 140 kilometres (87 miles) of walking tracks, admire the native bushland, marvel at the impressive rock formations and explore underground caves on a holiday centred around the outdoors. Whether you're out for a gentle stroll with the family or embarking on a vigorous multi-day trek with calf-burning descents to the valley floor, the Blue Mountains has a bushwalk to suit every level of ability and enthusiasm.

Included Meals: Breakfast

There's no better way to take in the breathtaking views of the UNESCO World Heritage-listed Blue Mountains than with our Unlimited Discovery Pass. 

Explore the area at your own pace, starting with a ride on the world's steepest railway into the Jamison Valley. Wander along kilometers of raised boardwalks through the rainforest, where you can spot Lyre Birds and ancient tree ferns among other flora and fauna. Hop on the Cableway to glide past the sandstone escarpment and Orphan Rock, then marvel at the iconic Three Sisters and the valley below from the Skyway. With the Unlimited Discovery Pass, you can experience all of this as many times as you can fit into a single day.

Included Meals: Breakfast

After an amazing trip, travel to Sydney Airport and return your rental vehicle prior to boarding your onward flight.

Today we say farewell. There maybe time for some last-minute excursions or shopping before you head home. We know you will enjoy your holiday and our promise to you is to make your travels through Australia as hassle-free and hospitable as possible - ensuring that today you leave with a camera full of photos, and huge smiles on your faces when recalling your holiday!

Included Meals: Breakfast

Approximate Distance: 65 km | 40 miles   Total Driving Time: 1 hour 30 mins