Kenny Escapes

With more than a decade running food and wine days across the Southern Highlands and South Coast, Kenny Escapes are the award-winning locals you want behind the wheel. Whether it's a hens day, a corporate group or four friends celebrating nothing in particular, they tailor every Bowral-based tour to your group — from $175 per person.

Your day is built around curated tastings at the region's most celebrated cellar doors, with expert tasting hosts at each winery making the wine as educational as it is fun. Choose a join-a-tour for individuals and small groups, or book a private charter for your own crowd. Departures come to you — Bowral, Mittagong, Moss Vale and surrounds, with pick-ups also available from Sydney, the Illawarra and the South Coast.

The Southern Highlands is cool-country wine territory just over an hour from Sydney — crisp, world-class cool-climate wines, historic estates and proper countryside calm. Kenny Escapes lean into the region's best: Bowral and Mittagong wineries, plus signature add-ons like a Milton Park high tea or a twilight wine-and-dinner tour that finishes at a local restaurant.

Eleven-plus years and an armful of awards mean they know which cellar door suits which group, and they customise every itinerary rather than running one fixed loop. The range is the real edge — half-day tasters, full-day escapes, high teas and twilight dinner tours all sit on the menu.

Tours run as half-day or full-day, private or join-a-tour, with prices from $175 per person depending on format. Departures are flexible across the Southern Highlands, Sydney, Illawarra and South Coast. Dietary needs and special occasions are easily accommodated — just flag them when you book.

Ready to book? Send Kenny Escapes an enquiry and they'll be in touch within 24 hours.