Southern Highlands Wine Tours · 2026

Southern Highlands Wine Tours.

Four bookable day tours through Bowral, Mittagong, Berrima and Moss Vale, with pickup from Sydney, Wollongong or anywhere in the Highlands, from $129 per person for groups of 30 or more.

Book a Tour → See the four tours and prices
Good Vibes Only
Our Highlands venues
Tailoring something special? Write to Jared jared@urbanlegendstourco.com Click to open a custom enquiry · replies in under 30 minutes weekdays
Prefer phone? 0434 363 911
From Sydney, Wollongong, Bowral, anywhere Flat day rate, no pickup surcharge 25+ partner venues curated 4.8 stars from 221 Google reviews Since 2016
25+
Partner Venues
4
Signature Tour Formats
221
Google Reviews
10 yrs
Curating the Region
See us in action

Real cellar doors. Real days out. Good Vibes Only.

Southern Highlands wine day Real cellar doors, real groups, real days
ReelOn the bus
Google Reviews
★★★★★
4.8 stars from 221 Google reviews. Scroll and read them all, right here.
Southern Highlands Wine Tours · 2026

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 cellar doors, a distillery scene and a couple of cracking breweries quietly putting out some of the best days out in NSW. We have spent ten years building relationships with the operators who care. Bendooley Estate in Berrima with the Berkelouw Book Barn. Tertini Wines, Artemis Wines & Distillery and Eden Brewery in Mittagong. Cherry Tree Hill Wines and Eling Forest Estate in Sutton Forest. Dawning Day Wines in Exeter. Sondara at Woodlands. Joadja Estate 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.

A guest holding a bottle at the Bendooley Estate cellar door bar, Berrima, wine racked behind her.
Bendooley Estate, Berrima

What's always included.

Tour packages are all-in. The price you see is the price you pay.
  • 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
Curated for
The crews who book Southern Highlands wine days with us.
Hens Parties Birthday Crews Wedding Bus-Outs Corporate Wine Days Sydney CBD Pickups Wollongong Departures Bowral Locals Macquarie Uni Groups Centennial Vineyards Weddings Tulip Time Day Trips Christmas Parties Bridal Showers
Good Vibes Only

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.

3-Winery Classic Wine + Spirit + Distillery Wine + Beer + Spirits + Cheese Winery + Brewery + 2 Distilleries + Cocktail Class Hens & Bucks Tours Wedding Guest Shuttles Corporate Wine Days Christmas Parties Bridal Showers Birthday Days Out Sydney CBD Pickup Wollongong Pickup Bowral Local Pickup Kangaroo Valley Pickup
Choose your tour

Four tour formats. One legendary day each.

Every Southern Highlands wine tour runs a full day of six hours or a half day of four, for the same price either way. Every tour includes premium seated cellar door tastings with all tasting fees paid, gourmet cheese and antipasto platters, and pickup from Sydney, Wollongong, Bowral and surrounds or Western Sydney. We pick the specific venues around your group, your taste and the time of year. Prices below are read live from our Rezdy catalog.

Tap your group size and we will show you what each person pays. Per-head prices fall as the group grows, so the number moves a long way between eight guests and thirty.
A long grazing board of cheese, crackers, grapes, watermelon and cured meats on a cellar door table, tasting glasses and wine barrels behind it.
Classic Wine Day

Southern Highlands 3 x Epic Winery Tour

6 hrs 3 wineries Platter lunch
Wine3 boutique winery visits, premium seated tastings, all tasting fees included. Cool-climate specialists: Pinot Noir, Chardonnay and sparkling.
FoodSubstantial cheese and antipasto platters, fruits, olives, cured meats, breads, oils and dips. All dietary requirements accommodated.
LunchPay on the day at our top recommended Highlands venue. Mains $25 to $36, wood-fired pizzas $23 to $26.
Transport14, 27, 41 and 57-seat luxury coaches, one pickup location included, guide who knows the region, your own playlist.
The more you bring, the less each person pays
4 to 6 guests$260 pp
7 to 9 guests$210 pp
10 to 14 guests$165 pp
15 to 19 guests$159 pp
20 to 29 guests$139 pp
30 to 200 guests$129 pp
Per head, live from Rezdy product 418906. Full day of six hours or half day of four, same price either way. A $200 deposit secures the booking with instant confirmation online. The Southern Highlands 3 x Epic Winery Tour is from $129 per person for groups of 30 or more, including three boutique winery visits, premium seated tastings with all fees paid, and gourmet cheese and antipasto platters. A group of eight pays $210 per person.
$200 deposit secures the booking, instant confirmation online · 7-day grace period before cancellation · final passenger numbers required 7 days before your tour · booking fee of 1.9%, about $3 per person, avoided on bank transfer
Get a Quote Book Now →
A group of twelve guests raising spirit glasses around a tasting table at a lookout over the Southern Highlands.
Wine + Spirits

Wine + Spirit Tasting & Distillery Tour

6 hrs Wine + spirits Platter lunch
Wine2 boutique winery visits with premium seated tastings, hand-picked for the region's best cool-climate wines. All tasting fees included.
SpiritsWelcome gin and tonic on arrival, guided distillery tour with behind-the-scenes access, guided tasting of 5 house-made gins, vodkas and liqueurs.
FoodGourmet cheese and antipasto platter included: cured meats, local artisan cheeses, seasonal fruits, olives and crackers.
Transport14, 27, 41 and 57-seat luxury coaches, one pickup location included, experienced guide, your own playlist.
The more you bring, the less each person pays
4 to 6 guests$260 pp
7 to 9 guests$210 pp
10 to 14 guests$159 pp
15 to 19 guests$149 pp
20 to 29 guests$139 pp
30 to 200 guests$129 pp
Per head, live from Rezdy product 390699. Full day of six hours or half day of four, same price either way. A $200 deposit secures the booking with instant confirmation online. The Southern Highlands Wine and Spirit Tasting and Distillery Tour is from $129 per person for groups of 30 or more, including two boutique wineries, a guided distillery tour, a tasting of five house-made spirits and a gourmet platter. A group of twelve pays $159 per person.
$200 deposit secures the booking, instant confirmation online · 7-day grace period before cancellation · final passenger numbers required 7 days before your tour · extra cocktails, coffee, donuts and gelato at the distillery are pay as you go
Get a Quote Book Now →
A large cheese and antipasto board of cured meats, olives, watermelon and crackers laid out in front of a row of Joadja Estate bottles.
Signature

Wine, Beer, Spirits & Cheese Platters

6 hrs Wine + beer + spirits Platter lunch
Wine2 boutique winery visits with premium seated tastings of the Highlands' cool-climate specialties. All tasting fees included.
BeerBeer or cocktail tasting at a local craft brewery, or two beers or wines at the lunch venue. All brewery fees included.
SpiritsWelcome gin and tonic on arrival, short guided distillery tour, generous guided tasting of 5 house-made gins, vodkas and liqueurs.
FoodSalami and jamón, 3 local artisan cheeses, seasonal fruits, Spanish olives and crackers, gluten-free available.
The more you bring, the less each person pays
4 to 6 guests$280 pp
7 to 9 guests$220 pp
10 to 14 guests$190 pp
15 to 19 guests$170 pp
20 to 29 guests$150 pp
30 to 200 guests$140 pp
Per head, live from Rezdy product 405410. Full day of six hours or half day of four, same price either way. A $200 deposit secures the booking with instant confirmation online. The Southern Highlands Wine, Beer, Spirits and Cheese Platters tour is from $140 per person for groups of 30 or more, including two wineries, a craft brewery, a distillery tasting of five house-made spirits and the region's best gourmet platters. A group of sixteen pays $170 per person.
$200 deposit secures the booking, instant confirmation online · 7-day grace period before cancellation · final passenger numbers required 7 days before your tour · optional cocktail making class $25 per person
Get a Quote Book Now →
Five guests seated around a wine-barrel table with a wood-fired pizza and a bottle of rosé, vineyard rows behind them.
The Big One

Winery + Brewery + 2 Distilleries + Cocktail Making Class

6 hrs 4 tastings + cocktail class Platter lunch
Wine1 boutique winery visit with a premium seated tasting of the Highlands' cool-climate specialties. All tasting fees included.
BeerBeer tasting paddle at a local craft brewery with multiple varieties to sample. All brewery fees included.
Spirits2 brand new local distilleries with exclusive access, welcome gin and tonic, guided tours at both venues and generous gin, vodka and liqueur tastings.
FoodSalami and jamón, 3 local artisan cheeses, seasonal fruits, Spanish olives, crackers, local condiments, dried fruits and nuts.
The more you bring, the less each person pays
4 to 6 guests$300 pp
7 to 9 guests$220 pp
10 to 14 guests$200 pp
15 to 19 guests$180 pp
20 to 29 guests$160 pp
30 to 200 guests$150 pp
Per head, live from Rezdy product 659949. Full day of six hours or half day of four, same price either way. A $200 deposit secures the booking with instant confirmation online. The Southern Highlands Winery, Brewery, 2 Distilleries and Cocktail Making Class tour is from $150 per person for groups of 30 or more, including a winery tasting, a brewery paddle, two distillery tours and a hands-on cocktail class. A group of twenty pays $160 per person.
$200 deposit secures the booking, instant confirmation online · 7-day grace period before cancellation · final passenger numbers required 7 days before your tour · extra cocktails, donuts and gelato are pay as you go at the venue
Get a Quote Book Now →

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.

Email Jared See All on Rezdy →
Lunch, done properly

Lunch is pay on the day, and that is deliberate.

A sit-down winery lunch in the Southern Highlands typically adds around $80 per person to the day, and it is locked in at the time you book, for everybody, whether they are hungry or not.

So our default is a recently renovated country pub we have got to know well. You order what you want on the day and pay for it there, so the cost sits with each guest rather than on your invoice. It is quiet, the food is good, the service is quick, and the table is genuinely yours for as long as you want it.

If you would rather have the winery lunch, say the word and we will book it. Plenty of groups do, particularly weddings and milestone birthdays, and the Highlands does them beautifully. We just would not put it on your quote by default.

What the pub gives your group

  • Pay as you go. No per-head lunch charge on your booking, no minimum spend, and no lunch numbers to lock in weeks out.
  • Full bar menu. Mains $25 to $36, wood-fired pizzas $23 to $26, premium steaks from $46. Light eaters and big appetites each pay their own way.
  • Service that fits the run. Food comes out quickly, which is what keeps a six-hour tour on schedule and gets you to the next cellar door unhurried.
  • Room to breathe. It sits off the standard tour circuit, so your group gets a calm dining room rather than a Saturday scrum.
  • Relaxed. No dress code, no set menu, no seating plan. After two cellar doors, most groups want exactly that.

Dietary requirements are handled at the venue on the day. Your driver calls ahead with numbers so the kitchen is ready for you.

The Region

Southern Highlands wineries, distilleries and breweries. 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.

The Southern Highlands wineries and cellar doors we actually run tours to are Bendooley Estate and Joadja Estate at Berrima, Cherry Tree Hill Wines and Eling Forest Estate at Sutton Forest, Sondara at Woodlands, Dawning Day Wines at Exeter, and Tertini Wines and Artemis Wines at Mittagong. In Bowral itself we use Millsheds distillery and bar, Berida Hotel, Tractorless Vineyard and The Briars, and for craft beer there is Eden Brewery at Mittagong. Almost all of them are cool-climate specialists, which is what the Southern Highlands is known for: Pinot Noir, Chardonnay and sparkling.

A Southern Highlands wine tour visits two to four of them in a day, and because Bowral is about 90 minutes from Sydney and 50 from Wollongong, it works comfortably as a day trip from either. Day trips from Mittagong, Moss Vale and Bowral itself are shorter again, so those groups usually add a fourth stop.

Bowral wineries and cellar doors

  • Millsheds distillery & bar, Bong Bong Street
  • Berida Hotel heritage hotel + dining
  • Bistro Sociale David Street
  • Tractorless Vineyard cellar door
  • The Briars tasting bar, est. 1845

Mittagong wineries and distilleries

  • Mittagong Hotel refurbished pub + dining
  • Artemis Wines cellar door & distillery
  • Tertini Wines cellar door
  • Eden Brewery taproom, Cavendish Street
  • Grow Wild Farm partner venue

Berrima wineries

  • Bendooley Estate cellar door + Book Barn
  • Joadja Estate cellar door

Exeter wineries

  • Dawning Day Wines cellar door + gin

Sutton Forest wineries

  • Cherry Tree Hill Wines cellar door
  • Eling Forest Estate cellar door + café

Woodlands

  • Sondara cellar door, Woodlands Road

...and more we save for our regulars.

Some of our favourite Southern Highlands venues are not on this list. The full route stays between us, our drivers, and the people who book. Book a tour and we'll show you the region the way we know it.

Book a Tour →
Local legends we back

Our Southern Highlands partners.

A handful of the cellar doors, distilleries and venues we are proud to send groups to across Bowral, Sutton Forest, Exeter and the wider Highlands.

Woodlands

Sondara Estate

Family-owned boutique vineyard on 100 acres at Woodlands, pouring estate-grown Sauvignon Blanc, Rosé and Pinot Noir. An intimate, appointment-only cellar door with local charcuterie boards.

Visit Sondara → Sutton Forest

Cherry Tree Hill Wines

Cool-climate Sutton Forest cellar door with a scenic hilltop setting. Elegant Highlands wines and a warm, relaxed welcome for groups.

Visit Cherry Tree Hill → Bowral

Millsheds Distillery & Bar

Distillery and bar in the heart of Bowral. Small-batch spirits and cocktails in a buzzy local spot, a cracking change of pace between cellar doors.

Visit Millsheds → Exeter

Dawning Day

Boutique Exeter winery and distillery making cool-climate wines and The Bandit gin, with a relaxed cellar door and seasonal produce boards.

Visit Dawning Day → Mittagong

Mittagong Hotel

A beautifully refurbished local pub in the heart of Mittagong with dining and function spaces. A relaxed, hearty lunch or last stop to round out a Highlands day.

Visit Mittagong Hotel →

For Southern Highlands venues

Run a Highlands cellar door, distillery or venue?

We bring premium groups through the Highlands every week and we love championing the places that look after them. If you would like to be featured here and have us send warm, well-organised groups your way, get in touch.

Get in touch about a partnership →
How it works

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.

1

Pickup, anywhere

Sydney CBD, Inner West, Wollongong, Bowral and surrounds, Western Sydney, Kangaroo Valley, the lower Blue Mountains. Tell us where and we come to you. One pickup location is included in the price, and extra travel time is included when your pickup sits further out than Bowral.

2

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.

3

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.

4

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.

Fifteen guests seated along a long table set with gin bottles and glassware in a Southern Highlands dining room.
Venue two, long table, fifteen guests. Highlands gin on the table before lunch.
Three Briars Est. 1845 tasting glasses on a bar, two of red wine and one of white.
Seated tasting at The Briars, Bowral. All tasting fees are already paid.
Beds of orange and white tulips in front of the rotunda at Corbett Gardens, Bowral, during Tulip Time.
Tulip Time, Corbett Gardens. September books out first, so plan early.
Who we do this for

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.

A white Urban Legends luxury coach used for Southern Highlands wedding guest shuttles.
For weddings

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.

Wedding venues we shuttle toCentennial Vineyards · Bendooley Estate · Peppers Manor House · Milton Park · Briars Country Lodge · Bowral Golf Club · Mount Ashby Estate
Get a wedding quote →
A hens party of about twenty guests posed together under the Joadja Vineyards and Winery cellar door sign.
For hens parties

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.

The hens day combo we book mostWinery + Distillery + Cocktail Class · Cheese platters loaded · Pickup from Sydney CBD · 4 to 18 guests
Book the hens day tour →
Sixteen guests seated along a long outdoor table under trees at a rustic Southern Highlands cellar door.
For corporates

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 Bendooley Estate's Book Barn restaurant or the Mittagong Hotel dining room. End-of-financial-year, EOFY incentives, off-sites and team builds.

Built forMacquarie University · Tech off-sites · Sales kickoffs · EOFY incentives · Board days · Christmas parties
Build a corporate day →
By the season

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.

Sep · Oct · Nov

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 Festival
Dec · Jan · Feb

Summer & long lunches

Outdoor cellar door seating, rosé season at Cherry Tree Hill and Sondara, picnic platters on Bendooley's Book Barn lawn. Christmas parties run thick through December. Weddings every weekend.

Christmas parties · Weddings
Mar · Apr · May

Autumn & harvest season

Cool climate vintages coming in. Vineyards turning gold. Bendooley's Book Barn restaurant runs harvest menus. Easter long weekend is one of the biggest wine days of the year here.

Easter · Harvest
Jun · Jul · Aug

Winter & 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 · Truffles
Year-round

Hens, 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.

Anytime
Already booked your venues?

Charter 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.

Get a Charter Quote See Bowral Charter Page →

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
The fleet

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.

A black and a silver Mercedes Sprinter parked side by side, both dressed with white wedding ribbons.
14-seat
Mercedes Sprinter VIP
Reclining seats. Bluetooth. Climate. Storage. Perfect for hens groups, intimate birthdays, four to fourteen guests.
Interior of an 18-seat Mercedes Sprinter with orange and purple LED strip lighting along the ceiling and a lit blue aisle.
18-seat
Mercedes Sprinter Luxury
Party bus. Leather seats. LED party lighting. Upgraded sound. Fifteen to eighteen guests. This is the hens day favourite.
Interior of a 27-seat coach with grey patterned reclining seats and an ocean outlook through the window.
27-seat
Yutong D7 Executive
2024 model. Premium upholstery. Woodgrain floors. USB at every seat. Twenty to twenty-seven guests. Corporate day perfect.
Interior aisle of a 41-seat coach with black and red reclining seats and blue aisle lighting.
41-seat
Luxury Coach
Black + leather. Woodgrain floors. Underfloor luggage. USB at every seat. Twenty-eight to forty-one guests. Wedding shuttle ready.
Interior of a 57-seat touring coach with grey and black leather seats, red headrests and overhead luggage racks.
57-seat
Touring Coach
The big one. Reclining leather, overhead racks, underfloor luggage. Forty-two to fifty-seven guests, or paired with the 41 for a wedding of a hundred plus.
Frequently asked

Southern Highlands wine tour questions.

How much do Southern Highlands wine tours cost?
Tour packages start at $129 per person for our 3-Winery Classic and Wine + Spirit Tasting & Distillery formats. The signature Wine, Beer, Spirits & Cheese tour is $140 per person. The big-day format with cocktail class is $150 per person. Every price is per head and falls as your group grows, across six bands from 4 guests to 200: on the 3-Winery Classic a group of eight pays $210 per person and a group of thirty pays $129. Every tour runs a full day of six hours or a half day of four for the same price, and all include seated tastings with fees paid, gourmet platters and pickup. Group minimums apply.
Where do you pick us up from?
Anywhere. Sydney CBD, Inner West, Eastern Suburbs, Wollongong, Bowral, Kangaroo Valley, the lower Blue Mountains, even Canberra on request. Same flat day rate, no pickup surcharge. We come to you, we return you to the same spot.
Which wineries do you visit?
We work with 25+ partner venues across Bowral, Mittagong, Berrima, Moss Vale, Sutton Forest, Exeter, Joadja and Kangaroo Valley. The specific three (or four) we pick on the day depends on your group, your taste, the season and what's open. That's our value-add. Our drivers curate the right route, so every tour is a little different. You can request specific venues if there's somewhere you want to land. Otherwise, trust the driver, they've done this a thousand times.
What is the minimum group size?
Public tour packages have small-group minimums (we'll confirm at the time of booking). For private charters or bespoke days, we'll run a tour for any group size up to 57 across the fleet. Email Jared with your numbers and the date and we'll come back with options.
Can we bring our own alcohol on the bus?
On the tour packages: no. The tastings are seated at venues and we don't permit BYO. On a private charter (where you've booked your own venues): yes, with written approval at the time of booking. Different products, different rules.
How far in advance should we book?
Two to four weeks ahead for standard tour dates. Two to three months ahead for peak season (Tulip Time in September, Christmas parties in December, weddings November to April). We can sometimes squeeze in last-minute requests, especially mid-week, so always worth asking.
Is lunch included?
Gourmet cheese and antipasto platters are included in every tour. Lunch itself is pay on the day, and that is deliberate: a sit-down winery lunch in the Southern Highlands typically adds around $80 per person and has to be locked in for the whole group when you book. Instead we stop at a recently renovated country pub where everyone orders what they want and pays for it there. Mains are $25 to $36, wood-fired pizzas $23 to $26 and premium steaks from $46, there is a full bar menu, and because it sits off the standard tour circuit your group gets a calm dining room and quick service that keeps the day on schedule. If you would rather have a winery lunch we will happily book one, it just is not on your quote by default.
Can you do hens parties, weddings or corporate days?
Yes to all three. Hens parties are one of our most-booked formats (the 18-seat party bus + cocktail class tour is a popular combo). Wedding guest shuttles to Centennial Vineyards, Bendooley Estate, Peppers Manor House and Milton Park are weekly bread and butter. Corporate days work brilliantly across the 27-seat Yutong or the 41-seat coach. Email Jared and we'll tailor the right format for your event.
What is Tulip Time and should we book around it?
Tulip Time is Bowral's flagship spring festival, running for two weeks every September at Corbett Gardens. Over 100,000 tulips bloom in a curated display. It pairs beautifully with a wine tour: morning at the tulips, afternoon at the cellar doors. Book three months ahead. Tulip Time weekends are our second-busiest weeks of the year after Christmas.
Can we customise the tour to visit specific wineries?
Yes. Tell us at the time of booking which venues you'd like to land at and we'll work the route around them where possible. For a fully bespoke private day (any venue, any route, any group size), book a charter rather than a tour package, and your driver runs the day to your runsheet. The cryptic value-add of the tour packages is that we curate when you don't have a preference, request a venue and we'll build the day around it instead.
Do you offer accessible wine tours for guests with mobility needs?
Yes, with a bit of notice. Our own coaches are standard-entry with steps, so for guests who need wheelchair access we bring in one of our accessible transport partners and run the day exactly as normal alongside it. For guests who are simply less steady on their feet, several Southern Highlands cellar doors have step-free access (Bendooley Estate, Cherry Tree Hill Wines, Sondara), and our 27-seat Yutong Executive has the lowest step-up of the fleet. Tell us at the time of booking and we'll route the day through venues your group can navigate comfortably. We've done many tours with wheelchair guests, walking-stick guests and elderly groups.
What happens if it rains?
Wine tours run rain, hail or shine. Every cellar door we visit has covered indoor tastings as the default, so weather barely impacts the experience. The bus is climate-controlled, you stay dry between venues. If it's a severe weather event (bushfire, flood, road closure) we'll work with you to reschedule at no charge.
Why Urban Legends

Why groups book Urban Legends.

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

4.8 stars from 221 Google reviews. Hens, weddings, corporates, birthday crews, all the same standard. The wins compound, the regulars rebook.

Explore more wine regions

The Highlands are just the beginning.

Same team, same fleet, same Good Vibes Only guarantee across every NSW wine region we run. Fancy Australia's oldest wine region next? Our Hunter Valley wine tours from Sydney run door to door from $129pp. Closer to the coast, our South Coast wine tours mix boutique wineries with sun and sea, or compare every region side by side on our Sydney wine tours hub.

Hunter Valley Wine Tours → All NSW Wine Tours →
Good Vibes Only

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.

Book a Tour → Email Jared
Tailoring something special? jared@urbanlegendstourco.com Replies in under 30 minutes weekdays
Prefer phone? 0434 363 911