Morning

Drive to Southern Highlands Drive

The drive from Sydney to Bowral takes roughly 1.5 hours via the Hume Highway — a pleasant cruise through the escarpment as the city gives way to rolling green hills. Put on a playlist and enjoy the descent into the Highlands.

Afternoon

Champagne High Tea Experience

A heritage mansion set among manicured gardens, Milton Park's high tea is one of the Highlands' most beloved rituals. Think finger sandwiches, warm scones with jam and cream, and — naturally — bubbles. A perfect birthday opener.

Late Afternoon

Wine Tasting Wine

A beautiful working estate with a renowned cellar door set inside a converted 1820s stone barn. Their cool-climate Rieslings and aromatic whites are well worth lingering over before heading to check in.

Evening · Check-in

Accommodation Stay

Your Airbnb in the historic village of Berrima — one of Australia's most intact Georgian towns. Unpack, settle in, and soak up the atmosphere before dinner.

Dinner

Eschalot Restaurant Dinner

A Highlands institution with an ever-changing menu rooted in local produce. Eschalot's warm stone interiors and candlelit tables make it a natural choice for a birthday dinner. Book ahead — it fills quickly.

Breakfast · 10:00 AM

Bowral Exploration Breakfast

A morning wander through Bowral's charming main street, starting with breakfast at The Press Shop — a beloved local café with excellent coffee and seasonal brunch plates. Take your time; this town rewards slow mornings.

Late Morning · 1:00 PM

Wine Tasting Wine

Set on 100 acres of Highlands farmland, Centennial is one of the region's most awarded producers. The cellar door is relaxed and welcoming — ideal for a long tasting session with a view over the vines.

Early Afternoon · 2:30 PM

Highland Cow Farm Experience Experience

A wildly charming encounter with a herd of fluffy Scottish Highland cattle on a working Highlands farm. You'll get up close for feeding and photos — the perfect unexpected birthday highlight. Bring snacks for the cows.

Mid Afternoon

Endota Spa — Massage Wellness

A well-earned massage at Endota Spa to melt away any road-trip stiffness. Book ahead to secure your preferred treatment — their signature rituals using Australian botanicals are particularly good.

Evening · 7:30 PM

Dinner & Drinks Dinner

Australia's oldest continually licensed hotel (operating since 1834), set in a beautifully preserved sandstone building. A roaring fire in winter, hearty pub classics, and a great selection of local wines. Exactly where you want to be on a cold Highlands evening.

Morning · 9:30 AM

Burradoo Farm Park Farm

A charming farm park with animals, gardens, and that unhurried country atmosphere that makes the Highlands so restorative. A lovely gentle start to the final morning before brunch.

Late Morning · 11:00 AM

Three Blue Ducks Brunch

The Highlands outpost of one of Australia's most beloved farm-to-table restaurants. Their brunch menu is grounded in produce grown right on the property — eggs, herbs, seasonal veg. The perfect farewell meal. Book your spot here →

Afternoon

Wine Tasting Wine

A final cellar door stop before heading back to Sydney — Dawning Day is a boutique producer with a relaxed, intimate tasting experience. Pick up a bottle or two to take home as a memento of the trip.