Southern Highlands wine tours from anywhere. Real wineries, real drivers, legendary days.
Premium wine tours through the Southern Highlands. Curated cellar doors, seated tastings, gourmet cheese platters and lunch built into every day. We pick you up from Sydney, Wollongong, Bowral, Kangaroo Valley, anywhere you are. Same flat day rate, no pickup surcharge. Bowral, Mittagong, Berrima, Moss Vale, Sutton Forest, Exeter, Joadja. Twenty-five-plus partner venues. Four signature tour formats. Ten years building the right relationships. Good Vibes Only.
Real cellar doors. Real days out. Good Vibes Only.
Sydney's most-loved Southern Highlands wine tour operator. Good Vibes Only.
Want a Southern Highlands wine tour that doesn't feel like every other Southern Highlands wine tour? You've found the right operator. Urban Legends Tour Co is a premium tour and charter company that has been running wine days through Bowral, Mittagong, Berrima, Moss Vale and Sutton Forest every single weekend since 2016. We own the fleet. We employ the drivers. We curate the route. And we know exactly which cellar door to send your group to depending on whether you're hens, corporate, a wedding party or four mates on a Saturday.
The Southern Highlands holds twenty-plus cellar doors, a growing distillery scene, a couple of cracking breweries, and a handful of farm-to-plate restaurants quietly putting out the best lunches in NSW. We have spent ten years building relationships with the operators who care. Centennial Vineyards in Bowral. Bendooley Estate with the Berkelouw Book Barn. Tertini Wines, Artemis Wines & Distillery, Eden Brewery and Renegade Spirits in Mittagong. Mount Ashby Estate with its hatted restaurant. Cherry Tree Hill in Sutton Forest. Dawning Day Wines and St. Maur Estate in Exeter. Joadja Distillery in the hills. We pick the right three for your group, your taste, your pace.
We pick you up anywhere. Sydney, Wollongong, Bowral, Kangaroo Valley, the lower Blue Mountains, even Canberra. Same flat day rate. No pickup surcharge. The bus comes to you. The fleet runs from the 14-seat Mercedes Sprinter VIP through the 18-seat Luxury Sprinter party bus, the 27-seat Yutong Executive, twin 41-seat luxury coaches, and partner 53 to 57-seat touring coaches for the bigger jobs. Wedding shuttles, hens, corporate days, multi-bus festivals, the lot, all handled by one team.
Premium Experience. Modern Fleet. Good Vibes Only.
What's always included.
- Professional driver · 10+ years average experience, knows the region inside out
- Cellar door tastings · seated, premium, no rushing through
- Gourmet cheese & antipasto platters · loaded on the bus
- Lunch built in · either platter-style or sit-down depending on the tour
- Pickup from anywhere · Sydney, Wollongong, Bowral, Kangaroo Valley, you choose
- Fuel and tolls · baked in
- Bluetooth audio · your playlist on the bus
- Climate control · every vehicle
- GST included · transparent pricing
One operator. Every Southern Highlands day, covered.
From a four-person Sprinter VIP wine day through to a 57-seat winery wedding shuttle, we handle every Southern Highlands tour end to end. You don't juggle three suppliers. One email, one team, one quality standard.
Four tour formats. One legendary day each.
Every tour runs around six hours. Every tour includes seated cellar door tastings, gourmet platters, and pickup from wherever you are. We pick the specific venues based on your group, your taste and the time of year. Click any tour to view live itineraries and book straight through Rezdy.
Southern Highlands 3 x Epic Winery Tour
- Three premium cellar door tastings, seated
- Gourmet cheese and antipasto platters on the bus
- Curated route across Bowral, Mittagong and Berrima
- Pickup from anywhere you are
Wine + Spirit Tasting & Distillery Tour
- Two premium wineries plus a curated distillery
- Seated wine tasting and spirit flight
- Gourmet cheese and antipasto platters on the bus
- Pickup from anywhere you are
Wine, Beer, Spirits & Cheese Platters
- Winery, brewery and distillery in one day
- Three seated tastings, three different drinks
- Gourmet cheese and antipasto platters loaded on the bus
- Most popular tour with mixed groups and corporate days
- Pickup from anywhere you are
Winery + Brewery + 2 Distilleries + Cocktail Making Class
- One winery, one brewery, TWO distilleries
- Hands-on cocktail making class
- Gourmet cheese and antipasto platters
- Perfect for hens, bucks and big birthdays
- Pickup from anywhere you are
Not sure which tour suits your group? Tell us about your day.
Hens, corporate, wedding shuttle, just-mates: we'll match you to the right format.
The Southern Highlands. Twenty-five-plus cellar doors, distilleries, breweries and farm restaurants. One driver who knows them all.
We've spent ten years building real relationships with the operators across Bowral, Mittagong, Berrima, Moss Vale, Sutton Forest, Exeter, Joadja and Kangaroo Valley. We won't tell you exactly which three (or four) we pick for your day. That's the value-add. Our drivers curate the right route for your group, your taste, the season and the time you've got. Below is a partial map of what's in play.
Bowral
- Centennial Vineyards cellar door + restaurant
- Bowral Cellar Door at The Mill
- Tractorless Vineyard cellar door
- Cuttaway Hill Wines cellar door
- SoHi Spirits Bong Bong Street
- Millsheds distillery & bar
- Berida Hotel heritage hotel + dining
- Sondara partner venue
Mittagong
- Artemis Wines & Distillery cellar door
- Tertini Wines cellar door
- Eden Brewery taproom
- Renegade Spirits distillery
- Mittagong Hotel refurbished pub + functions
- Pepper Green Farm kitchen garden restaurant
- Grow Wild Farm partner venue
Berrima
- Bendooley Estate cellar door + Book Barn
- Joadja Estate cellar door
- PepperGreen Estate cellar door + dining
Exeter
- St. Maur Estate cellar door
- Dawning Day Wines cellar door + gin
Sutton Forest
- Cherry Tree Hill Wines cellar door
- Eling Forest Estate cellar door + café
- Sutton Forest Estate Wines cellar door
Moss Vale
- Mount Ashby Estate cellar door + hatted restaurant
- Southern Highlands Brewing brewery
Joadja & Kangaroo Valley
- Joadja Distillery gin and whisky
- Yarrawa Estate Kangaroo Valley cellar door
The shape of your day.
Every tour follows the same rough shape. The venues change. The pace adjusts to your group. The driver makes the call on the day.
Pickup, anywhere
Sydney CBD, Inner West, Wollongong, Bowral, Kangaroo Valley, the lower Blue Mountains. Tell us where, we come to you. Same flat day rate, no surcharge for distance.
Stop one. The opener.
First cellar door, distillery or brewery. Seated tasting. The driver picks the venue based on your group, the day, the season. You taste, you chat, you take a beat.
The middle. Lunch + venue two.
Gourmet cheese and antipasto platters loaded on the bus. Or a sit-down lunch at one of the hatted restaurants. Then the second venue. Different drink, different vibe.
The finale. Drop you home.
One more curated stop. Cocktail class, distillery flight, scenic last pour. Then the driver returns you to your pickup point. The whole day is around six hours.
Three crews. One signature day each.
The Southern Highlands works for wildly different days out. We build the tour around your group, not the other way around.
Southern Highlands wedding transport
Bridal party transfers, guest shuttles from Sydney CBD or Wollongong, and end-of-night returns. Multi-bus combos handle guest counts of 50, 100, even 150+. Wedding planners book us back month after month.
Southern Highlands hens day tours
The 18-seat Mercedes Sprinter party bus, LED lighting, your playlist on Bluetooth. Cocktail class tour with three tastings + gourmet platters. The hens day Sydney brides actually rave about.
Corporate wine days & team builds
Premium 27-seat Yutong Executive or twin 41-seat coaches. Pickup from your office, day at the cellar doors, sit-down lunch at Mount Ashby's hatted restaurant or Centennial Vineyards. End-of-financial-year, EOFY incentives, off-sites and team builds.
The Southern Highlands changes with the season.
Every cellar door has a different vibe in March than September. Here's what to expect across the year so you can pick the right time for your day.
Spring & Tulip Time
Bowral's signature festival. Corbett Gardens explodes with 100,000 tulips for two weeks every September. Wine tours pair beautifully with a Tulip Time walk. Book three months ahead.
Tulip Time FestivalSummer & long lunches
Outdoor cellar door seating, frosé and rosé season at Centennial, picnic platters at Bendooley's Book Barn lawn. Christmas parties run thick through December. Weddings every weekend.
Christmas parties · WeddingsAutumn & harvest season
Cool climate vintages coming in. Vineyards turning gold. Mount Ashby's hatted restaurant runs harvest menus. Easter long weekend is one of the biggest wine days of the year here.
Easter · HarvestWinter & log fires
Mulled wine at Bendooley by the fire. Truffle season around Bowral. Christmas in July menus at the country house hotels. Quieter cellar doors, deeper conversations.
Christmas in July · TrufflesHens, weddings, corporates
Some days don't care what month it is. Hens parties, wedding shuttles and corporate days run every weekend, every season. We have a date that suits your group.
AnytimeCharter just the bus.
Sometimes you've already locked in the cellar doors yourself. The bridal party knows the route. The corporate organiser has booked direct. You don't need a curated tour, you need a premium bus with a great driver to handle the logistics.
That's a charter, not a tour. Pure transport, your venues, your runsheet. NSW Saturday floor for a 14-seater wine day is around $1,500 all-in. The 18-seater party bus is around $1,650. The 27-seater Yutong Executive is around $1,800. The 41-seat luxury coach is around $2,200. Distance, fuel and tolls are all baked in.
Charter rates · Southern Highlands Saturday floor
- 14-seat Sprinter VIPfrom $1,500
- 18-seat Sprinter Luxury party busfrom $1,650
- 27-seat Yutong Executivefrom $1,800
- 41-seat luxury coachfrom $2,200
- 53 to 57-seat touring coachPOA
One operator. Five vehicles. Every group size.
Each tour includes the right bus for your group. You only pay per-person on the tour, but here's what you're riding in.
Southern Highlands wine tour questions.
How much do Southern Highlands wine tours cost?
Where do you pick us up from?
Which wineries do you visit?
What is the minimum group size?
Can we bring our own alcohol on the bus?
How far in advance should we book?
Is lunch included?
Can you do hens parties, weddings or corporate days?
What is Tulip Time and should we book around it?
Can we customise the tour to visit specific wineries?
Do you offer accessible wine tours for guests with mobility needs?
What happens if it rains?
Why book with us, not them.
Premium modern fleet
We own every vehicle. Mercedes Sprinters, Yutong Executive, twin 41-seat luxury coaches. Maintained obsessively, six-month HVIS inspected.
Drivers who know the region
Ten years running Southern Highlands wine days every weekend. They know which venue suits your group before you've finished your second glass.
Real relationships
We've spent ten years building partnerships with the cellar doors, distilleries and farm restaurants who actually care about a great day out.
Good Vibes Only, guaranteed
213 five-star Google reviews. Hens, weddings, corporates, birthday crews, all the same standard. The wins compound, the regulars rebook.
Ready for your legendary day?
Book one of the four tour formats on Rezdy, or email Jared to tailor a private day for your group.
Tailoring something special? jared@urbanlegendstourco.com Replies in under 30 minutes weekdays