Sydney Wine Tours.
Winery Day Trips With Your Own Coach & Driver.
Private winery days in the Hunter Valley, Southern Highlands and South Coast, door to door from anywhere in Sydney on luxury 14 to 41 seat coaches. From $129 per person for groups of 30 or more, including cellar door tastings and all tasting fees.
Wine tours from Sydney. Door to door.
Every wine tour we run starts at your door, not at a meeting point. Pickup anywhere in Sydney, the Inner West, the Eastern Suburbs, the North Shore, the Hills, the Shire or Western Sydney, and the same coach brings you home.
Sydney to the Hunter Valley
North up the M1 through Pokolbin and Broke Fordwich. The biggest cellar door choice in New South Wales and the region most groups picture when they say wine tour.
Hunter Valley wine tours →Sydney to the Southern Highlands
South west to Bowral, Mittagong and Moss Vale. Cool climate wine, closer to town, and the shortest drive of the three, which buys you more time at the cellar door.
Southern Highlands wine tours →Sydney to the South Coast
Down through Berry, Shoalhaven and Gerringong. Wine, beer and the coast in one day, and the one region where lawn bowls is genuinely part of the itinerary.
South Coast wine tours →Urban Legends runs private wine tours from Sydney to three New South Wales wine regions. The Hunter Valley is about two hours north of Sydney and starts from $129 per person for groups of 30 or more. The Southern Highlands is about an hour and a half south west of Sydney and also starts from $129 per person for groups of 30 or more. The South Coast is about two hours south of Sydney and starts from $199 per person for groups of 20 or more. Every price includes cellar door tastings and all tasting fees, and every tour includes door to door pickup anywhere in Sydney on a luxury coach with a driver. Smaller groups pay a higher per head rate, starting at $240 per person for a group of four to six.
See an NSW winery day for yourself.
Three regions, one trusted operator.
Urban Legends runs guided, all-inclusive winery days across NSW's best wine regions, the Hunter Valley, South Coast and Southern Highlands. Fully customisable, with local guides, premium seated tastings and a cheese and produce platter on the bus.
We look after groups of up to 200. You pick your own wineries or run one of our tried-and-tested itineraries, and we handle the vehicles, the cellar door bookings, the tastings and the logistics. Your group just shows up and has the best day.
Since 2016 we have run hundreds of winery days for hens parties, birthdays, corporate teams and milestone celebrations. Pick the region that suits your group, and we will build the day around you.
Want the bus without the guided package? We also run private charter across all three regions for groups who have already sorted their own wineries. NSW bus hire details here.
Pick your wine country.
Three New South Wales wine regions, each with its own character and its own per head pricing. Prices below are live from our booking system. Full itineraries, every package and live dates are on each region page.
Hunter Valley
Southern Highlands
South Coast
Included on every wine tour, in all three regions
Never included on any tour: bottles you buy to take home, meals beyond the platter, and optional distillery or chocolate tastings, which run $5 to $25 per person and are paid at the venue. A $200 deposit secures any booking with instant confirmation online. Final balance and final numbers are due two weeks before your tour, and your detailed itinerary is sent once the deposit is received.
Four steps to a legendary day.
No spreadsheets, no chasing venues, no stress. Here is exactly how a winery day with us comes together.
Tell us the details
Send us your date, group size and the vibe you are after, then request a quote. Hens day, corporate team, big birthday, we have done them all.
We build the itinerary
We put together a custom itinerary at the best wineries for your group, or run one of our tried-and-tested routes if you would rather leave it to us.
Confirm with a deposit
Lock in your date with a $200 deposit. We confirm the venues, send you the run sheet, and the balance is due before the day.
We pick you up
Your driver collects the group door-to-door. You sit back, relax and enjoy the day. We handle the road, the bookings and the timing.
Every kind of wine day.
Whatever the occasion, we tailor the day around your group. Tell us what you are celebrating and we will build it.
Day trips
Pick an itinerary or choose your own wineries. Add a lunch stop or a cheese and chocolate tasting. A full day out across your chosen region.
Book now →Overnight packages
A weekend or midweek escape with the wineries on tap. We sort the accommodation and the route so your whole trip runs smoothly start to finish.
Book now →Hens parties
A classy, all-inclusive hen do for the wine-loving bride. Private bus, premium tastings and a day that runs like clockwork while you focus on the fun.
Book now →Birthdays
Food, fun, friends and wine. The easiest way to spend a milestone birthday with the people who matter, without anyone playing designated driver.
Book now →Corporate & team building
A premium team day that runs itself. We handle the logistics, the bookings and the schedule so the team relaxes and the leaders look good. Corporate rates available.
Request a quote →Something else?
Weddings, wine clubs, family get-togethers or a group of mates who just love good wine. If it involves a cellar door and a great day out, we can build it.
Request a quote →
South Coast Wine, Beer & Lawn Bowls
A relaxed coastal day that mixes great wine, a local brew and a proper laugh on the green. Jared's pick for groups in the Berry and Gerringong area.
- Wine tasting at a local cellar door, with a bottle or two expected to come home with you
- A local brewery beer paddle to mix things up
- Lawn bowls with mountain and ocean views at Gerringong Bowls and Recreation Club
- A relaxed coastal tapas-style social tasting with ocean views to finish
Ideal for groups who want a bit of everything: wine, beer, a game and a great feed, all in one of the prettiest pockets of the NSW coast.
Book now →Why book your wine tour with us.
Custom-made, every time
No two days are the same. We build every tour around your group, and you pick your own wineries or follow our route.
Door-to-door pickup
We collect your group from wherever they are, Sydney, Wollongong or further afield, and bring you home again.
Modern luxury buses
Air-conditioned, comfortable modern buses for groups up to 200, with Bluetooth so you bring your own playlist.
The best venues
We eat at the best restaurants and support local wineries we know and trust, so every stop on the day is a good one.
Our NSW wine country partners.
A few of the exceptional cellar doors, breweries and venues we are proud to work with across our three regions.
Stoic Brewing
One of our favourite venues on the coast, hands down. An independent Gerringong brewery pouring small-batch beers right by the water, with a relaxed taproom that loves hosting groups. The beer-paddle stop on our South Coast wine, beer and lawn bowls day.
Visit Stoic Brewing → Shoalhaven HeadsCoolangatta Estate
A historic Shoalhaven estate and one of the South Coast's best-known cellar doors, set among heritage grounds at the foot of Mount Coolangatta.
Visit Coolangatta Estate → ShoalhavenTwo Figs Winery
A relaxed Shoalhaven cellar door with sweeping valley views, a favourite stop for groups who want great wine and an even better outlook.
Visit Two Figs Winery → BerrySilos Estate
A boutique Berry winery and restaurant set on a picturesque property, a beautiful spot for tastings and a long South Coast lunch.
Visit Silos Estate → CambewarraCambewarra Estate
A family-run cellar door nestled below Cambewarra Mountain, known for its warm welcome and easy-drinking Shoalhaven wines.
Visit Cambewarra Estate → GerringongCrooked River Wines
A scenic Gerringong winery and cafe with ocean and mountain views, a regular highlight on our South Coast days.
Visit Crooked River Wines → ShoalhavenMountain Ridge Wines
A welcoming Shoalhaven cellar door pouring estate-grown wines, a relaxed stop with a genuine local feel.
Visit Mountain Ridge Wines → GerringongThe Hill Bar and Kitchen
An easy going Gerringong bar and kitchen with hearty share plates and cold drinks. A favourite lunch stop between South Coast tastings.
Visit The Hill → GerringongThe Noble Gerringong
A stylish Gerringong restaurant and bar putting local produce front and centre. A relaxed sit-down lunch on a South Coast day.
Visit The Noble → Werri BeachGerringong Bowlo
Barefoot bowls with an ocean breeze at Werri Beach. Social, easy and a guaranteed laugh between tastings.
Visit Gerringong Bowlo → WollongongSouth Coast Distillery
A Wollongong distillery crafting small-batch gin and spirits, a cracking tasting stop to start or finish a South Coast run.
Visit South Coast Distillery →Bimbadgen Estate
Iconic Hunter Valley estate with a restaurant, sweeping vineyard views and a legendary summer concert series.
Visit Bimbadgen → PokolbinHope Estate
A large estate known for its concert amphitheatre, expansive grounds and broad range of varietals. A standout for bigger groups.
Visit Hope Estate → LovedaleEmma's Cottage Vineyard
Boutique family-run cellar door in the heart of the Lovedale wine corridor. Intimate tastings with a genuine local feel.
Visit Emma's Cottage → PokolbinHorner Wines
Boutique Palmers Lane cellar door in Pokolbin making small-batch wines with a genuine, family-run welcome.
Visit Horner Wines → PokolbinVinden Wines
Boutique Pokolbin winery on Gillards Road with a laid-back cellar door and a loyal following for its small-batch drops.
Visit Vinden Wines → PokolbinFour Pines at the Farm
The 4 Pines brewery taproom at the Hunter Resort in Pokolbin. Craft beer, easy food and wide farm surrounds, a welcome change of pace on a mixed Valley day.
Visit Four Pines at the Farm → Broke FordwichRiver Flats Estate
A scenic Broke Fordwich estate and a favourite stop on our Broke Fordwich days.
Visit River Flats Estate → BrokeWhispering Brook
Family estate in Broke crafting elegant wines and estate-pressed olive oil, with a warm, personal cellar door experience.
Visit Whispering Brook → BrokeBARE Nature'sKin
Handmade olive oil and goats milk soaps, skincare and hands-on workshops in a cottage at Broke's River Flats Estate. A lovely non-wine stop with a personal touch.
Visit BARE Nature'sKin → PokolbinMoorebank Vineyard
A boutique Pokolbin vineyard we love sending groups to for a relaxed, genuine cellar-door welcome.
Visit Moorebank Vineyard → NulkabaThe Valley Brewhouse
A craft brewery and food stop in Nulkaba with a relaxed pub atmosphere, a welcome change of pace on a mixed Hunter Valley day.
Visit The Valley Brewhouse →Sondara
A boutique vineyard in the Southern Highlands, a relaxed and welcoming stop on a Highlands wine tasting day.
Visit Sondara → Sutton ForestCherry Tree Hill Wines
A cool-climate Sutton Forest cellar door with a scenic hilltop setting and a warm welcome for groups.
Visit Cherry Tree Hill → BowralMillsheds Distillery & Bar
A distillery and bar in the heart of Bowral pouring small-batch spirits and cocktails, a great change of pace between cellar doors.
Visit Millsheds → ExeterDawning Day
A boutique Exeter winery and distillery making cool-climate wines and The Bandit gin, with a relaxed cellar door.
Visit Dawning Day → MittagongMittagong Hotel
A beautifully refurbished Mittagong pub with dining and function spaces, a hearty lunch or final stop on a Highlands day.
Visit Mittagong Hotel →For venues and cellar doors
Run a cellar door, brewery, restaurant or venue in NSW wine country?
We bring premium groups through the Hunter Valley, South Coast and Southern 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 →"Very professional, quick and easy to work with. Would highly recommend this company and would rebook in a second if needed for a future event! Thank you!!"
"Celebrated 60th birthday on winery tour, was the best day, all taken care of, all you do is enjoy the day. Bus driver Sam was amazing, very helpful, friendly. Highly recommend for a stress free, fun day."
"Absolutely no regrets choosing Urban Legends for our wedding transport. Jared is a great, easygoing guy and was so flexible on the day when timings and pickups needed changing at the last minute."
NSW winery tour questions, answered.
How do I make a booking?
Request a quote via our contact page, email jared@urbanlegendstourco.com or call 0434 363 911 with your region, group size and preferred date. We send back a tailored quote, then organise payment. A $200 deposit confirms the tour and we take care of the rest.
Do I have to make a deposit?
Yes. A $200 deposit confirms the tour and locks in your date. The balance is due before the day of the tour. We send you the bank details and a clear summary once you are ready to book.
How many wineries can I visit?
You can visit up to 4 wineries in a day, though we recommend 3 so the day is not rushed. That leaves plenty of time for seated tastings, lunch and the drive between cellar doors without watching the clock.
Why choose Urban Legends?
Every tour is private, fully customisable and local, and we specialise in groups. Across the Hunter Valley, South Coast and Southern Highlands we handle the vehicles, the cellar door bookings, the tastings and the platter, so your group just shows up and enjoys the day.
How much does a wine tour from Sydney cost?
It depends on the region and, more than anything, on how many people are coming. Hunter Valley and Southern Highlands tours start from $129 per person for groups of 30 or more, and South Coast starts from $199 per person for groups of 20 or more. A smaller group of four to six pays a higher per head rate, from $240 per person in the Hunter Valley. Every one of those prices includes cellar door tastings, all tasting fees and door to door transport on your own coach.
Is a wine tour cheaper if we bring more people?
Yes, and the difference is bigger than most people expect. The per head price falls as the group grows, so a Hunter Valley group of eight pays $220 per person while a group of thirty pays $129 per person on the same tour. If you are close to the next bracket it is worth asking two more friends. The full band table for every tour is on each region page.
How far is the Hunter Valley from Sydney?
About two hours door to door, north up the M1 to Pokolbin and Broke Fordwich. For comparison, the Southern Highlands is about an hour and a half south west, and the South Coast is about two hours south. Because we pick up at your address rather than a meeting point, the drive starts when you are already on board with a coffee.
Which NSW wine region should we pick?
If you want the widest cellar door choice and the classic Hunter name, go Hunter Valley. If you want the shortest drive and more time actually tasting, go Southern Highlands, which is the closest of the three. If you want wine, beer, the coast and a game of lawn bowls in the same day, go South Coast. Tell us the vibe and we will tell you honestly which one suits your group.
Do you pick up from my house in Sydney?
Yes. Every wine tour is door to door. We pick up anywhere in Sydney, including the Inner West, the Eastern Suburbs, the North Shore, the Northern Beaches, the Hills, the Sutherland Shire and Western Sydney, and the same coach brings you home at the end of the day. Multiple pickup points for one group are fine, just tell us the addresses when you book.
Do you have a wine tour bus for large groups?
Yes. We run a luxury fleet from 14 seat Mercedes Sprinters up to 41 seat luxury midi coaches, with larger coaches available, and we regularly run two or three vehicles in convoy for the biggest groups. That means one operator is responsible for your whole day rather than a broker juggling other people's buses.
What size bus do you send for a wine tour?
We match the coach to the group rather than the other way around. A group of ten to fourteen usually takes the 18 or 27 seater, twenty five to thirty takes the 41 seat midi, and anything above that goes to a larger coach or two vehicles in convoy. If you are between sizes we will normally put you on the bigger one so there is room to spread out, which on a wine tour matters more than it sounds.
Can we choose our own wineries?
Yes. You can build the day around the cellar doors you want, or run one of our itineraries that we already know works. Most groups start from one of ours and swap a stop or two. Either way we make the cellar door bookings and pay the tasting fees, so nobody in your group is chasing venues or splitting a bill on the day.
Can you run an accessible wine tour?
Tell us what you need and we will work it out with you before you book. Step heights vary across our vehicles, and cellar door access varies a lot from venue to venue, so the honest answer is that it depends on the combination. Give us your requirements and your preferred region and we will confirm which vehicle and which venues will genuinely work rather than promising it on a web page and sorting it out on the day.
Can we buy wine to take home?
Absolutely, and most groups do. There is luggage space on every coach and the driver will help you load it. Bottles you buy at the cellar door are paid for at the venue and are not part of the tour price. It is one of the better reasons to be on a bus rather than driving yourselves.
Do you run wine tours for hens parties and corporate groups?
Both, constantly. Hens parties, birthdays, milestone celebrations, work days out and corporate team days are the bulk of what we run, and there is a dedicated Classy Hunter Valley Hens Party Wine Tour in the booking system. Corporate groups usually want a tighter schedule and an invoice, and hens groups usually want a playlist and a longer lunch. We are comfortable with either.
Do you run half day wine tours?
Yes, in the Hunter Valley. There are half day options with one epic winery plus a brewery or distillery, and a half day with three Legends wineries including a chocolate, cheese and olive tasting. Both start from $129 per person for groups of 20 or more. Half days suit groups who want to be home for dinner or who are pairing the tour with something else that evening.
When do we need to confirm final numbers?
A $200 deposit secures the booking with instant confirmation online. Your final balance and final numbers are due two weeks before the tour, and your detailed itinerary is sent once the deposit is received. If your numbers move before that two week mark we simply re-price you into the right band.
NSW wine country.
From the Hunter Valley north of Sydney to the South Coast and Southern Highlands to the south, we roam the best wine regions in the state.
Our three NSW wine regions sit within easy reach of Sydney and Wollongong: the Hunter Valley about 2 hours north, the South Coast and Southern Highlands to the south. Your driver knows the back roads between every cellar door.
Ready for a legendary day out?
Pick your region, tell us your date and group size, and we will build the day around you. Book online for a fixed departure, or get a quote for a private group day.