The Southern Highlands is the kind of place that makes you forget you’re just 90 minutes from Sydney. With its rolling hills, historic towns, and hidden waterfalls, it’s the perfect weekend escape. Here’s how to make the most of 48 hours in this enchanting region.

This two-day itinerary captures the essence of what makes the Highlands special: historic towns that feel frozen in time, hidden waterfalls that reward those willing to venture off the main road, and enough food and wine to satisfy the most demanding epicurean. While you could spend weeks exploring every corner of this region, a weekend is enough to fall in love with its charm.

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Getting There

While trains run to some Highland towns, this itinerary requires a car to make the most of your weekend. 

Most major rental companies have locations throughout Sydney, but I recommend you skip the airport pickup and head to a suburban location instead. It will generally save you money and make returning the car easier too.

Expect to pay between $70-100 per day for a small car – perfect for navigating the region’s winding country roads. I usually use Discover Cars to compare options from multiple providers in one place, often finding better rates than booking direct. I like that there is a free cancellation policy meaning if the weather looks suspect or something changes I can amend my dates or cancel without any stress. Booking a few months ahead usually secures the best deals so being able to cancel is a great option.

For international visitors, your home license is fine as long as it’s in English (if not, grab an International Driving Permit before you leave home). Book ahead during spring and summer – rental cars can be scarce during the popular Tulip Time Festival.

Day 1: Bowral Base & Southern Explorer

Morning Itinerary (8am – 12:30pm)

Leave Sydney by 8:00am to beat the traffic and arrive in Bowral around 9:30am, just as the town is coming to life.

Start your highlands experience at The Plantation. This converted warehouse café isn’t just breakfast – it’s your introduction to highland hospitality.

While you’re there, grab some provisions for tomorrow’s picnic – their house-made preserves and local cheeses are worth the splurge.

Late morning offers a choice: culture vultures should head to the Bradman Museum (allow 90 minutes), while vintage lovers will want to lose themselves in Dirty Janes Antique Market.

Pro tip: If you choose antique shopping, start at the back corner of Dirty Janes where the best pieces hide, and save time for tea in their upstairs salon.

Afternoon Adventures (12:30pm – 5pm)

By now, the clock’s pushing 12:30pm, perfect timing for the scenic 15-minute drive to Berrima. This historic village is arguably the best-preserved Georgian village in mainland Australia, and as you drive down its main street, you’ll feel like you’ve stepped back into the 1830s.

Gumnut Patisserie makes fantastic meat pies and their vanilla slice is an award winner. There is not much room to eat in so perhaps get them to take away and find a nice spot in the sun for an impromtu picnic.

If you fancy a sit down meal The Surveyor General Inn is a good option. It’s one of the oldest pubs in NSW and makes a mean steak sandwich.

Post-lunch, the Berrima River Walk beckons. This gentle 1.8km loop offers your best chance of spotting the local platypus population – they’re most active near the old wooden bridge.

Time your walk to finish around 3:30pm, perfect for your booking at Bendooley Estate. Yes, it’s popular, but this book-lined cellar door offers some of the region’s finest cool-climate wines, especially magical in the late afternoon light. You may want to skip the walk if you are a book lover and spend extra time here.

Evening in Bowral (6:30pm onwards)

After freshening up at your accommodation, follow the fairy lights down Green Lane to one of Bowral’s worst-kept secrets: Harry’s. Hidden away from the main street, this local favorite serves modern Australian cuisine with Asian influences.

Book ahead and request a table near the kitchen to watch the chefs at work. The wine list heavily features local vintages – ask your server about any small producers you might have missed during your tastings.

Cap off your night with a nightcap at The Grand Bowral. This historic pub has been serving thirsty travelers since 1888, and its recent renovation has kept all the charm while adding modern comforts.

Day 2: Waterfalls & Wilderness

Day two switches gears from historic charm to natural wonders. There are several impressive waterfalls in the National Parks that surround the Highlands.

Morning Explorer (7am – 10:30am)

If you need a coffee to get going pop into Nicks on Bong Bong Street. They open at 7am on weekends and serve quality coffee made with care.

The 30-minute drive to Robertson takes you through some of the highlands’ most photogenic countryside. Time your drive for early morning when the mist hangs low over the dairy farms and, in spring, the canola fields paint the landscape in brilliant yellow.

Make a quick but essential stop at Moonacres Kitchen – their sourdough and sweet treats are legendary among locals, and their coffee will power you through the morning’s adventures.

Waterfall Circuit (10:30am – 2:30pm)

We will dip into Morton and Budderoo National Parks today and but if you are staying longer in the region check out Macquarie Pass for more beautiful falls.

Your first stop is Carrington Falls, where morning light creates rainbow mist above the cascading water.

While the main viewing platform offers spectacular vistas, don’s miss nearby Hindmarsh Lookout for views back across the highlands that will remind you of the Blue Mountains.

If you are doing well for time take a short detour here to Nellies Glen which is a gorgeous little spot only a few minutes drive away.

From here you head back through Robertson to your next stop.

The drive to Fitzroy Falls takes you through Robertson’s famous potato-growing country. Time your arrival for lunch, finding a perfect picnic spot near the visitor center.

The resident lyrebirds are usually most active during lunch hours, and on clear days, the valley views stretch all the way to the coast.

The West Rim walking track (1.6km return) offers the best perspectives of both the falls and the escarpment – allow about an hour if you want to stop for photos.

Final Afternoon (2:30pm – 6pm)

For your final highlands indulgence, Mount Ashby Estate awaits. Unlike the bigger cellar doors, this boutique winery feels like stumbling upon a French country manor.

The cellar door, housed in an antique-filled cottage, offers an unhurried tasting experience that’s worth lingering over. Watch the resident horses graze in nearby paddocks while sampling their excellent cool-climate wines.

If you can tear yourself away by 4:30pm, loop back through Bowral for any last-minute shopping or that one antique piece you’ve been thinking about since yesterday.

Timing tip: Aim to leave by 6pm to avoid both highway traffic and kangaroos (they’re most active at dusk). As you wind your way back to the city, you’ll already be planning your next highlands escape – perhaps in a different season, when the landscape transforms entirely.

Where to Stay: Choosing Your Highland Base

Your choice of accommodation can transform a good highlands weekend into an unforgettable escape. While there are charming options throughout the region, basing yourself in Bowral puts you in the perfect position for this itinerary.

Luxury Stays ($300+ per night)

• Milton Park Country House: The grande dame of highland hotels, set on 300 acres of manicured gardens. Book a garden suite for views over the formal roses, and don’t miss the heated pool and day spa. Worth the splurge for special occasions.
• Berida Hotel: For luxury with a more intimate feel, this art deco gem in central Bowral combines period charm with modern comforts. The excellent on-site restaurant means you don’t have to venture out on cold highland nights. You can find it priced under $250 midweek.

Mid-Range Options ($180-300 per night)

• The Sebel Bowral Heritage Park: Perfect for longer stays, with apartment-style rooms and full kitchens. The central location means you can walk to dinner after a day of exploring.
• Bowral Road Art Gallery Bed and Breakfast: Where warm highland hospitality meets insider knowledge. The hosts’ local tips often lead to the best discoveries.

When to Visit: Making the Most of Every Season

The Southern Highlands transforms dramatically with each season, making it worth multiple visits throughout the year.

Here’s what to expect and how to plan:

Spring (September-November)

• Peak Season: Tulip Time Festival (September) draws crowds to Corbett Gardens
• Weather: 16-22°C, occasional rain showers
• Must Do: Garden tours, outdoor cafes, vineyard picnics
• Book Ahead: Accommodation fills months in advance for September weekends
• Insider Tip: Visit mid-week during Tulip Time to avoid the biggest crowds

Autumn (March-May)

• Local’s Choice: Best combination of weather and value
• Weather: 12-20°C, crisp mornings, stable conditions
• Must Do: Photography along tree-lined streets, hiking trails
• Highlight: Autumn leaves peak in late April
• Insider Tip: Book a cottage with a fireplace for cosy evenings

Winter (June-August)

• Best Value: Lowest accommodation rates
• Weather: 3-12°C, occasional frost and fog
• Must Do: Wine tastings, antiquing, pub lunches by the fire
• Perfect For: Romantic weekends and atmospheric photos
• Insider Tip: Early morning fog creates magical photo opportunities

Summer (December-February)

• Quieter Season: Escape Sydney’s heat
• Weather: 18-28°C, cooler than Sydney
• Must Do: Early morning walks, outdoor dining, swimming holes
• Watch For: Occasional heat waves
• Insider Tip: Book accommodation with air conditioning; highland buildings can retain heat

Essential Tips for Your Highland Weekend

Before You Go

• Book restaurants at least two weeks ahead for weekend lunches
• Download offline Google Maps – mobile coverage is patchy around waterfalls
• Join the Southern Highlands What’s On Facebook group for current events
• Check cellar door opening hours – many smaller wineries close mid-week

Getting Around

• Fill up in Bowral or Mittagong – rural servos often close early
• Allow extra driving time for fog between May and August
• Keep wildlife in mind – avoid driving at dawn and dusk
• Park in council lots in Bowral – street parking has strict time limits

Making the Most of Your Visit

• Start shopping early – most stores close by 4pm (3pm in winter)
• Catch the golden hour at Bowral’s Bradman Oval or Mount Gibraltar
• Visit antique stores mid-week for better deals and first picks
• Check the Mittagong Information Centre for seasonal walking maps

Local Secrets

• Follow @visitsouthernhighlands on Instagram for event updates
• Check the Southern Highland News for local market dates
• Ask your accommodation host about resident wombats and kangaroos

Ready for Your Highland Adventure?

The Southern Highlands offers that perfect blend of accessibility and escape – close enough for a weekend but far enough to feel like you’ve truly gotten away. While this itinerary covers the highlights, you’ll likely discover your own favorite spots along the way: perhaps a hidden antique store in Exeter, a secret picnic spot near Fitzroy Falls, or a friendly local who shares their personal wine cellar recommendations.

The real magic of the highlands lies in its ability to surprise, whether it’s a platypus sighting along the Berrima River Walk or the perfect scone in an unexpected café. So while this guide gives you a framework, leave room for spontaneity – some of the best highland moments happen when you follow that intriguing side road or accept a local’s suggestion.

Remember to book your accommodation and key restaurants early, especially for spring and autumn visits. Then pack your layers, charge your camera, and get ready to discover why this region has been captivating Sydney weekenders for over a century.

Have questions about planning your highland escape? Drop them in the comments below, or share your own highland discoveries – we’d love to hear about your favorite spots!

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