Top Sydney Holidays in 2026

Get the most out of your day in the Hunter Valley by combining two of its features—wine and native Australian wildlife—in a single itinerary. With a guide in the lead and transportation all arranged in advance, learn about the famous wine-producing region and its animal inhabitants through stops at a local wildlife park and several boutique wineries. You can also sample cheese and indulge in a winery lunch (extra cost).

Experience the Hunter Valley’s refined side on this small-group luxury wine tour designed for travellers who value quality over quantity. Your day begins with a premium tasting at Mount Pleasant, one of the region’s most historic wineries, served with cheese and olives. Next, enjoy an intimate tasting at Thomas Allen Wines—a boutique cellar door rarely offered to tour groups. Lunch is at the acclaimed Bistro Molines, where guests pay on the day and can choose their own two-course menu overlooking the vines. After lunch, visit Mount View Estate, a stunning new cellar door perched high above the valley. Enjoy a guided tasting while taking in one of the most spectacular views in the Hunter. Travelling in a luxury vehicle with an expert local guide, you’ll avoid crowded tourist stops and enjoy more relaxed, personalised experiences. Perfect for couples, friends, celebrations, and anyone seeking a more elevated Hunter Valley wine tour.

Meet wild kangaroos on our private farm, an experience exclusive to our guests and unlike anywhere else in Australia. With a private guide and luxury vehicle for your group alone, this is the Southern Highlands at its finest: dramatic waterfalls, colonial villages, cool climate wine and quiet countryside. Your day begins at Fitzroy Falls, where forested cliffs drop into deep valleys, before continuing to Berrima, a village of sandstone cottages and colonial character. At Bendooley Estate, enjoy a wine tasting among lakeside vines, included in your tour. In Bowral, boutique and antique stores offer a slower rhythm, with time for lunch at one of the town's favourite spots. The day concludes at Boscobel, where your guide leads you through quiet paddocks as mobs of kangaroos graze freely around you. A day of beauty, taste, history and gentle wilderness.

What better way to experience Sydney Harbour with a party! Come enjoy great food, music and company. Get out your scrunchies, sweatbands and fluro spandex and join us for a funky, old-school boat party! Girls (and guys) just wanna have fun aboard Sydney Harbour's hottest retro boat party! Get immersed in a retro setting, grab a drink at the bar and get settled in for an array of delicious bites served to your table. Don't forget to grab some goodies at the 90s candy bar and enjoy the sights of stunning Sydney Harbour from the observation deck. Before you know it, you'll be ready to cut your best shapes on the dance floor as your retro DJ plays the most bangin' beats from the 80's & 90's. Retro attire is not compulsory, but definitely encouraged - you won't be the ony one! Prizes and giveaways for best dressed dudes and dudettes. Cruise Inclusions: 3-hour cruise Fresh harvest board & hot finger food Fully licensed bar All night retro DJ 90s nostalgia candy bar

Discover Australia's Soul in Every Sip. From vine to glass, immerse yourself in a truly distinctive Australian wine adventure, where passion flows as freely as the wine itself. You will get to taste wines from all over Australia that are strictly on-premise and can't be purchased unless you visit the cellar doors individually. We take the hassle out of you travelling and doing your own research. Enjoy a truly immersive experience with the iconic Sydney Harbour Bridge as your backdrop.

Discover the secrets of Australian wine on this private, full-day tour of the Hunter Valley, including hotel pick-up. Travel in style in a luxury vehicle, stopping for tours and tastings at up to four boutique wineries. Indulge in wine, and sample a range of semillon, chardonnay, verdelho, and Shiraz wines.

Celebrate Australia Day out on the water aboard a Tall Ship. Cruise around past some of Sydney’s most famous attractions, join in on the evening traditional Tall Ships Race, and watch the fireworks show over Sydney Harbour. Onboard, enjoy an Aussie-style barbecue, beverages like bubbly, wine, soft drinks, juices, and water, and live music and entertainment.

Explore the Blue Mountains with ease on this full-day private tour from Sydney. Stop at Featherdale Wildlife Park on the way, then see landmarks like the Three Sisters, Cahill's Lookout and Wentworth Falls. Enjoy the rides at Scenic World (extra cost), then return to Sydney Harbour via a scenic cruise down the Parramatta River to Sydney Harbour.

Explore the Southern Highlands region of New South Wales on this private day trip from Sydney. This relaxing escape from the city provides scenic views of rolling green hills and stops at historical villages and manicured gardens, as well as wine tasting. You’ll visit Red Cow Farm, Fitzroy Falls, and the heritage towns of Bowral and Berrima, where you can enjoy some free time.

Experience the very best of Hunter Valley and Australian native wildlife on your luxury private day tour. As we head to the northern suburbs of Sydney, the first stop of the tour, you can experience the free roaming of Australian animals at the Hunter Valley Wildlife Park. Following that, you will reveal the best of Shiraz the valley can offer and the scenic beauty of Pokolbin in the care of your expert guide. Tours start at 7.30 am (flexible) with pick up from your hotel, travelling aboard a new minivan/sedan (depending on the group size) with leather interiors, and climate control, and enjoying chilled refreshments throughout the day. The Hunter Valley is famous for Shiraz, handmade cheese and chocolates. Highlights - A luxury private tour Hotel pick up and drop off at Sydney CBD See free-roaming Australian native wildlife Visit 2 boutique wineries + distillery Learn about Hunter Valley and wine styles Visit the chocolate shop and local distillery or cheese factory Flexibility

Join us for a night of world class comedy when the Showcase comes to The Comedy Store. We handpick the funniest and freshest acts of Sydney's biggest annual comedy event, squeeze them into one hilarious line-up and deliver them to all corners of Sydney! "The comedians in the showcase all knew what they had to do to get a laugh and had the crowd in constant stitches..."- AU Review PLEASE NOTE THAT ALL TICKETS PURCHASES INCLUDE 1X DRINK VOUCHER. This show is a Sydney Comedy Festival Showcase.

Discover the Southern Highlands Through Exceptional Winery Tours (only 1.5hours away from Sydney's CBD). Immerse yourself in the charm, elegance, and flavor of New South Wales’ premier cool-climate wine region with Southern Highland Winery Tours. We offer curated, guided tours to the region’s finest wineries, blending scenic countryside vistas with unforgettable tasting experiences. Whether you're a seasoned connoisseur or a curious newcomer, our tours cater to all, providing insider access, local insights, and seamless transport. Join us for a relaxed yet refined journey through rolling vineyards, boutique cellar doors, and award-winning estates. Perfect for couples, corporate groups, or special celebrations, our tours are designed to showcase the best of Southern Highland hospitality, food, and wine.

Explore all things ghostly as we visit Sydney's most haunted pubs. Hear about the notorious Rocks Push, vanishing sailors and the Woman In Black. Walk with the disturbed spirits in the Cellar at The Waterloo Hotel, said to be one of Australia's most haunted Hotels. You will discover the seedy underworld of Australia's original seaport. There is also plenty of opportunity enroute to calm your nerves at a pub haunted by a pianist, a drinking den at the center of an epidemic and a murder hot spot. Tour includes visiting haunted, historic pubs with access to an original Cellar.

Escape the busy streets of Sydney and discover Australia’s oldest wine region on this full-day tour to Hunter Valley. Alongside a private guide, visit a few local vineyards to tour their facilities and learn about the winemaking process. Enjoy private, guided tastings with the winemakers and feast on a delicious 2-course lunch at an award-winning restaurant.

Discover the haunting charm of Sydney’s Rocks district on this immersive ghost tour. Begin at Cadman’s Cottage, a dwelling seeped in centuries-old stories and rumored ghostly presences. Wander through the maze of cobbled streets, including Kendall Lane, whispering tales of desperation and crime. Explore enigmatic sites like the eerie Merchant’s House and Greenway Lane, each holding their unique spectral tales. Uncover the somber history of the Nurse’s Walk, once a hospital site that stirs a sense of unsettling illness. The journey concludes at Observatory Hill, offering panoramic views of Sydney and chilling tales of lingering spirits. Experience these sites and more, as you delve into the heart of Sydney’s spooky past.

Luxury Private Day Tour: Sydney to Canberra Explore Australia’s Capital in Style Embark on a full-day luxury private tour from Sydney to Canberra in a premium Mercedes-Benz vehicle, designed for travellers seeking comfort, elegance, and a personalized experience. Discover the highlights of Australia’s capital city and iconic attractions along the way, all at your own pace with a private guide-chauffeur. Whether you're a history lover, a political enthusiast, or simply looking to explore somewhere new, this tour blends cultural richness, scenic landscapes, and VIP comfort for a memorable day out. Return to Sydney by approximately 5:30 pm

The Hunter Valley's breweries are spread out enough that visiting several usually means skipping the beer and driving. Hand the driving over on this guided tour and tasting experience. Cruise between three local breweries in an air-conditioned vehicle, sample craft beer and cider, and tuck into a delicious lunch and snacks.

Explore one of Australia’s hidden gems with a private full-day tour to the Southern Highlands and Kangaroo Valley. Take a scenic drive, that takes in Sea Cliff bridge, one of the largest blowholes in the world, and a local winery. Depending on the itinerary you select you'll either spend some time observing native Australian wildlife at Symbio Park or the wonder of Carrington Falls.

Located on level two of the iconic and heritage listed Queen Victoria Building, entering Esquire feels like stepping into a New York supper club, complete with re-imagined Modern Australian cuisine alongside an array of the world’s best wines, spirits and hand-crafted cocktails. A dark, oak bar framed with mosaic and parquetry flooring, soft leather seating and sensuous low lights all make the most of the QVB’s historical Romanesque revival architecture. shared menu for the whole table ESQ is the perfect destination to eat, drink and play. Menu subject to seasonal change

Avoid the risk of drinking and driving when you take a private tour of the Hunter Valley’s wineries from Sydney. Every member of your group can sample wines at a selection of the region’s premier wineries. Learn more about local varieties and wine-making processes and get the chance to sample wines (extra cost).

Experience the very best of Hunter Valley on your luxury private day tour starting from Sydney. Your day tour reveals the best Hunter Valley wines with cheese pairing. Additionally, enjoy horse riding whilst sighting native wildlife. Tours start at a time that suits you with pick up from your hotel, travelling aboard a new minivan and enjoying chilled bottled water throughout the day. Highlights - • A luxury private wine and horses’ day out from Sydney • Visit boutique cellar doors • Take in awesome and inspiring views • Taste some of the most delicious wines • Horse riding • Cheese and wine pairing • Enjoy a scrumptious lunch from local restaurants • Personable, informed tour guide • Feel you’ve experienced the real Hunter Valley wine country!

Join Our Unique Paint and Sip Classes in Sydney! Embark on a creative journey with us and experience an evening like no other. Our skilled instructors provide step-by-step guidance, ensuring everyone from beginners to seasoned artists can create a masterpiece. All materials are provided—canvas, paints, brushes, and aprons—so just bring your enthusiasm! Enjoy a relaxed atmosphere with non-alcoholic beverages, or bring your own wine. We also offer Apple tea and Turkish delights for a unique touch. Our fun, casual setting is perfect for unwinding, making new friends, and painting the night away. Leave with a beautiful artwork to display at home or give as a gift. Please note, that our classes require a minimum of 3 participants to proceed. If this minimum is not met, we will contact you to reschedule or offer a free upgrade to another lesson. We appreciate your understanding and look forward to creating with you! Book now to secure your canvas and unleash your inner artist!

Rocky Road Tours isn’t just another tour company—it’s a personalized, unforgettable experience led by a passionate local guide Rocky who truly cares about making every trip special. Here’s what makes Rocky Road Tours stand out: 1. A One-of-a-Kind, Personal Touch - You’re the guide, the driver, and the heart of the experience. Unlike big companies with rotating staff, guests get consistency, expertise, and a warm, friendly host every time. - Small, intimate groups mean a relaxed, engaging atmosphere—no getting lost in a crowd. 2. Tailored and Flexible Tours - Not a one-size-fits-all tour. You customize experiences to match guests’ interests, whether it’s wine, food, nature, or hidden gems. - Off-the-beaten-path stops—you take guests where big bus tours don’t go, uncovering local secrets and unique spots. 3. Stress-Free and Seamless Travel - I don’t just drive and drop off—I bring the region to life with stories, history, and insider tips.

Experience the Hunter Valley your way on a fully private wine tour from Sydney, created exclusively for your group. Travel in a clean, air-conditioned premium vehicle with your dedicated local driver-guide, with no shared vehicle and no need to worry about driving after visiting the region’s cellar doors. Unlike a fixed group tour, you can choose your preferred wineries, subject to availability, or let us help shape the day around your interests. Enjoy the freedom to explore at a relaxed pace, with the itinerary tailored around your group and venue availability. Private door-to-door pickup and return make the journey easy and comfortable, with bottled water and onboard Wi-Fi provided. Ideal for couples, friends, families and special occasions, this experience combines the freedom of a personalised Hunter Valley day with the convenience of having your transport and logistics taken care of.