Just a short drive from Sydney, the Southern Highlands offers an elegant escape from the pace of the city.
Think rolling countryside, historic villages, boutique hotels, long lunches, cool-climate wineries and beautiful gardens. All without needing to board a plane. For a luxury weekend getaway from Sydney, the Southern Highlands strikes the right balance between indulgence and relaxation.
Rather than packing every hour with activities, the region rewards a slower approach. Think a leisurely breakfast, a country drive, an afternoon of wine tasting, and a long dinner by the fire.
Sydney to the Southern Highlands
Approximately 90 minutes to 2 hours southwest of Sydney by car, the Southern Highlands gives you the freedom to take the scenic route and stop along the way.
For a weekend itinerary, Bowral makes an excellent base. As the largest town in the Southern Highlands, it offers a good selection of restaurants, boutiques, galleries, and stunning accommodation.
Friday: Sydney to Bowral
Leave Sydney and Take the Scenic Route
For a relaxed weekend, aim to leave Sydney in the late morning rather than rushing out at sunrise. The drive south takes you away from Sydney’s urban landscape and towards the greener, more open scenery of the Southern Highlands.
The region is known for its produce-driven dining, with menus that make the most of local ingredients and the area’s cool-climate setting. Because of this, Bowral is the perfect opportunity to begin the weekend slowly, ideally with a long lunch accompanied by a regional wine.
Settle Into the Southern Highlands
Your accommodation should be part of the experience rather than simply somewhere to sleep.
Look for Southern Highlands luxury hotel or boutique country stay with character, beautiful grounds and somewhere to relax after exploring. If you’re staying in Bowral, you’re close to restaurants and shops while still feeling removed from Sydney’s fast paced environment.
Spend your afternoon settling in, enjoying the property and resisting the urge to over-plan.
For your first evening, keep things sophisticated but relaxed.
Bowral has become one of the Southern Highlands’ most appealing dining destinations, with restaurants ran from modern Australian dining to intimate European-inspired venues.
A long dinner with a bottle of wine is the ideal way to start the weekend. Don’t schedule anything immediately after dinner. One of the pleasures of a country escape is letting dinner stretch well beyond expected. Allow yourself to fully take in and appreciate the countryside.
Saturday: Wineries, Berrima and a Long Lunch
Saturday is the main exploring day, combining the Southern Highlands’ food and wine scene with one of its most beautiful historic villages. Just 10 minutes from Bowral you’ll find yourself engulfed in a beautifully preserved Georgian village.
Start with a slow breakfast and coffee before heading out for the day. If the weather is good, take your time. There is no need to leave Bowral early. The region is best experienced at a leisurely pace.
The Southern Highlands has developed a strong reputation for cool-climate wines, particularly varieties such as Pinot Noir and Chardonnay. Rather than attempting to visit as many wineries as possible, choose two or three and give yourself enough time to actually enjoy them.
Berrima is small enough to explore on foot, making it ideal for a slow paced afternoon. Wander along the historic main street, browse shops and galleries and take in the sandstone architecture.
Berrima is particularly atmospheric in the cooler months, when the Southern Highlands’ crisp weather makes the regions fireplaces, cozy interiors and country pubs especially appealing.
Evening: Return to Bowral
Head back to your accommodation before dinner and give yourself time to relax. A luxury weekend should not feel like a road trip with a checklist.
Enjoy the hotel, take a bath, read a book or simply sit outside with a glass of wine.
For Saturday night, book the restaurant in advance. Whether you choose an intimate restaurant in Bowral of a destination dining experience elsewhere in the Highlands, make dinner the final event of the day.
No late-night itinerary, no rushing. Just dinner, wine and a quiet country evening.
Sunday: Gardens, Bowral and Back to Sydney
Sunday should be deliberately slower. Enjoy breakfast at your accommodation before checking out and exploring more of Bowral.
For something different, visit the Bradman Museum and International Cricket Hall of Fame, dedicated to Sir Donald Bradman, who grew up in Bowral. Even for non-cricket enthusiasts, it provides an interesting connection to the town’s history.
If museums aren’t your priority, use the morning to explore Bowral’s boutiques, antique stores, and galleries instead.
If you’re visiting during spring, make time for Corbett Gardens, particularly when the annual tulip displays are in bloom. The gardens are one of Bowral’s most recognizable attractions and make a particularly beautiful addition to a spring Southern Highlands itinerary.
Outside tulip season, you can swap this for another garden, country walk or leisurely cafe stop.
One Last Southern Highlands Meal
Before driving back to Sydney, stop for one final lunch. Keep it relaxed, the goal is to finish the weekend feeling restored rather than squeezing in one last attraction.
After lunch, begin the drive back to Sydney. Allow around 2 hours, depending on your final destination.
The weekend may be short, but the beauty of the Southern Highlands is that you don’t need a week to feel like you’ve properly escaped the city.
