Bowral
A storybook little town, 690m up in the Southern Highlands and about an hour and a half from Sydney. Tree-lined streets, boutique shops spilling onto the footpath, cosy cafes tucked into old cottages, and a main strip with a whole different, slower kind of magic to it.
My experience & recommendations
- Feels like a different world only ~1.5 hours from Sydney. Big Gilmore Girls energy: cosy cafes, little art galleries, vintage boutiques and a slower pace of life.
- Grab a pastry at The Gumnut Patisserie, famous for a reason, genuinely insane.
- Spend a chunk of your day at Dirty Janes, an antique store that just keeps going, easy to get a little lost in. The potting shed section is the standout.
- There are a few lookouts around town worth a short stroll for, an easy way to break up all the shopping with a view.
Refuel stop
Finish the day at Harry's on Green Lane, solid comfort food, exactly what you want after a day of wandering.
Wineries worth the detour
The Cellar Door at Bendooley Estate
Berrima, NSW
Tasting: $15pp (groups of 1–9)
Premium upgrade: $30pp
Map: The Cellar Door at Bendooley Estate ↗
- The customer service here was incredible, honestly what made the whole experience. Our host was lovely, so funny, and never once pushy, just really good vibes.
- Loved the indoor/outdoor feel of the place, we sat inside with it fully open, looking straight out at the vineyard.
- The wine itself was delicious, we each picked a different one to taste each round, worked really well for comparing notes.
Sondara
Woodlands, NSW
Tasting: $20pp
Map: Sondara ↗
- This was my favourite of the three wineries. The location is stunning, situated on 100 acres of pure serenity in the Southern Highlands with highland cows, sheep and even baby goats on the land, which we were allowed to go and feed.
- It's set in a big open barn with eating outside too, by firepits. The goats were roaming around inside during the tasting, which was adorable, and getting to feed them is honestly what made it so good.
- The customer service was phenomenal, everyone was really chatty and interested, and the wine tasting itself was really impressive, they even added a small charcuterie pairing which was a lovely touch.
Artemis Wines
Mittagong, NSW
Tasting: $20pp
Map: Artemis Wines ↗
- I loved the wine here so much, they had some lovely choices and we got to try six.
- The vibe was relaxed, outside with loads of space, I'd recommend this one for families as it's a bit bigger and less intimate.
- Apparently they're famous for their pizza too, but we didn't get to try it!
- The cellar door itself is built from recycled river redgum, giving it a lovely rustic feel.