Bowral & Southern Highlands

Bowral & Southern Highlands

About Our Southern Highlands And Bowral Wine Tours

Our Bowral and Southern Highlands wine tours definitely do not disappoint. Snuggle up for a cold climate experience and embrace all that the boutique wineries this area has to offer.

Just a short drive from Sydney, the Southern Highland wine region is famous for award-winning restaurants and wine tastings. Experience the best food and wines fresh from the cellar with a group of friends or in a more intimate one-on-one day trip.

You will be taken through the picturesque countryside in comfort enabling you to relax and take in the beautiful scenery.

Our Southern Highlands wine tours are private and individualised so you and your group of guests have the whole vehicle and driver all to yourselves. We can host groups between 3 – 20 people (**NB Due to COVID restrictions there may be some limitations with venues**)

We work with you to customise your day – no tour is identical. We can include your favourite winery, visit your favourite cellar doors or additional stops by prior arrangement (*pending availability).

Included in the price:

  • Tours depart anywhere between Illawarra and Southern Highlands area at a location of your choice.
  • Comfortable door-to-door transport in an air-conditioned/heated vehicle
  • Our departure and return times are flexible – we work with you to customise your day (A typical day tour starts at 9:30am and ends at 5:30pm).
  • Visit 3 wineries and enjoy private tastings with experienced wine makers of the region (tasting fee’s included).
  • Enjoy a delicious cheese platter with one of your tastings either before or after lunch.
  • Lunch with a complimentary glass of wine at one of the wineries.
  • Option to substitute one of your winery stops with a visit to The Mill in Bowral for cheese or chocolate.


3 people $340 per person

4 people $270 per person

5-7 people $250 per person

8-13 people $195 per person

14-20 people $170 per person


** Contact us directly to book tours **

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Hear what our customers say

The tour was amazing value for money – we had a private guided tour at 3 local wineries along with beautiful cheese platters and lunch supplied. Ben our driver was organised, knowledgeable and friendly.

He had everything covered right down to an iPhone cable for music and rubbish bags for on the bus, and who could forget his epic photography skills for the many group shots we asked him to take. The guys were so accommodating with the many requests and changes we made, nothing was any trouble for them.

10/10 from me I couldn’t fault the service.

Brooke Ker

I use Creasy Bear Tours because Ben always gets me from A to B, and with a smile! Whether it’s an airport transfer for business or a winery tour with the girls, Ben is always professional, prompt and a pleasure to deal with. Plus, his prices are hugely competitive. I’d recommend Creasy Bear Tours to anyone after top quality service they can rely on.

Lisa Burling


Well done to Ben and Creasy Bear Tours. We engaged Ben to look after my birthday party guests staying in Bowral. The party was on a farm. Ben picked people up from around the Southern Highlands to do a small wine tour. That was lots of fun! He dropped everyone back at the motels and then picked them up to bring all to the party at High Range. At the end of the party Ben returned everyone late at night. Great driver, friendly and knowledgeable – made the experience for all my guests better.

Big thank you. 5 star.


Winery Tours
Service Type
Winery Tours
Provider Name
Creasy Bear Tours,Southern Highlands-2576,
Telephone No.0416642657
Bowral and Southern Highlands, NSW
Unique winery tours of Bowral and The Southern Highlands designed just for you

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