Choose by the day you want, not by the longest list of stops. The Blue Mountains suit a lookout or short walk followed by lunch in a village such as Leura or Katoomba, and the rail connection makes a car-free visit realistic. The Southern Highlands suit a slower drive through towns such as Bowral and Berrima, with cafes, local produce and a booked lunch. The Hunter Valley is the food-and-wine option, but it is farther from Sydney and works best when you allow a long day or a night away.
If wine tasting is part of the plan, book a tour or arrange a driver who will not drink. Check opening days and travel time before reserving lunch, then keep the rest of the itinerary light.
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