The NSW wine country, done properly.
Guided, all-inclusive winery days across the Hunter Valley, South Coast and Southern Highlands. Your own luxury bus, premium seated tastings at the region's best cellar doors, a cheese and produce platter, and a local guide who handles every booking. You pick your wineries or run a tried-and-tested itinerary. We sort the rest.
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 10 to 57. 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 NSW wine regions, each with its own character. Tap through for itineraries, pricing and live booking dates.
Hunter Valley
Explore the vineyards, sample vodka or taste delicious cheese, just 2 hours from Sydney.
Explore Hunter Valley tours →
South Coast
Where wine and food meet the ocean. Beautiful Shoalhaven wineries, restaurants and coastal lookouts.
Explore South Coast tours →
Southern Highlands
Premium cellar doors and wineries in the picturesque Southern Highlands.
Explore Southern Highlands tours →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 10 to 57 guests, 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
An independent Gerringong brewery pouring small-batch beers right by the coast. 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 →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 →Centennial Vineyards
One of the Southern Highlands' largest and best-known cellar doors, with a restaurant and cool-climate wines just outside Bowral.
Visit Centennial Vineyards → BerrimaBendooley Estate
A much-loved Berrima estate combining a cellar door, a book barn and a restaurant, a signature Southern Highlands stop.
Visit Bendooley Estate → Southern HighlandsSondara
A boutique vineyard in the Southern Highlands, a relaxed and welcoming stop on a Highlands wine tasting day.
Visit Sondara →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.
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.