Urban Legends Tour Co

Rated 4.8 across 218 Google reviews, Urban Legends Tour Co has run Southern Highlands wine days every single weekend since 2016 — and it shows. They own the fleet, employ the drivers and curate the route, so your day through Bowral, Mittagong and Berrima feels handled from pick-up to drop-off, all from $129 per person.

Days are built around three carefully chosen cellar doors with seated tastings, a gourmet cheese platter and lunch built into every itinerary. They'll collect you from Sydney, Wollongong, Bowral or Kangaroo Valley on a flat day rate — no pick-up surcharge wherever you start. Whether you're hens, corporate, a wedding party or four mates on a Saturday, the route is matched to your group.

The Southern Highlands holds twenty-plus cellar doors, a growing distillery scene and some of the best farm-to-plate lunches in NSW. Urban Legends have spent ten years building relationships with the producers who care — Centennial Vineyards in Bowral, Bendooley Estate beside the Berkelouw Book Barn, Tertini Wines, Mount Ashby Estate and its hatted restaurant, Cherry Tree Hill in Sutton Forest, and Joadja Distillery up in the hills, among others.

The edge is control and consistency: because they own the buses and employ their drivers, nothing gets sub-contracted and the quality holds every weekend. With 25-plus partner venues and four signature tour formats, they pick the right three stops for your group's taste and pace rather than running a fixed loop.

Tours are full-day with lunch and tastings included, from $129 per person. Pick-ups run from Sydney, Wollongong, Bowral, Kangaroo Valley and anywhere in between on a flat day rate. Formats suit hens, corporate, weddings and social groups — book early, as weekend dates fill fast.

Ready to book? Send Urban Legends Tour Co an enquiry and they'll be in touch within 24 hours.