Top Sydney Seasonal & Special Occasions

No trip to Sydney is complete without a visit to the Sydney Opera House, the city’s most famous building. And what better to do when visiting the Sydney Opera House than to spend a pleasant evening inside enjoying an opera performance. Celebrating 70 dazzling years since its Broadway debut, Julie Andrews’ production of Lerner and Loewe’s My Fair Lady returns to the Sydney Opera House. A heartwarming story of transformation and identity, My Fair Lady brims with razor-sharp wit, unforgettable characters, and a glorious score including ‘Wouldn’t It Be Loverly?’, ‘I Could Have Danced All Night’ and ‘Get Me to the Church on Time’. Don’t miss this rare chance to see a sparkling gem of theatrical history, hailed by The New York Times as “one of the best musicals of the century”. Before the performance or at interval, enjoy drinks purchased from the Sydney Opera House Northern or Southern Foyer Bar, where you can admire stunning views across Sydney Harbour.

Enjoy unobstructed views of Sydney Harbour's landmarks from a 35-foot (10.5-meter) catamaran during this evening cruise. Sail past the Sydney Opera House and the Sydney Harbour Bridge as the sky shifts from sunset colors to city lights. Light snacks and soft drinks or water are provided on board, and you are welcome to bring your own alcoholic beverages with no corkage fee. Settle in and enjoy the views without the hassle of battling the crowds on land.

Fine-tune your appreciation of Australian wines and cuisine on this full-day tasting tour of the Hunter Valley from Sydney. Discover Australia's oldest wine region at premium wineries and learn about the terroir from wine experts, with wine tastings included. Allow yourself to indulge while your guide navigates the roads between the city and the Valley.

Understanding Sydney’s layered history can be difficult without local context, particularly in areas shaped by both Indigenous heritage and European colonies. This guided pub walking tour explores The Rocks, an area with deep cultural significance, through stories connected to its long-standing pubs. Walk between venues with a local guide, enjoy four included drinks, and learn how social gathering places reflected changing communities over time.

Indulge your inner foodie as you discover the fine wines and culinary delights of Australia’s famous Hunter Valley. Set out from Sydney on a full-day trip, stopping to enjoy tours and tastings at the region’s most prestigious boutique wineries. Along the way, tuck into a delicious lunch at a local restaurant and sample regional cheeses and chocolates.

Experience one of Australia’s most impressive buildings—the Sydney Opera House—on a guided tour followed by lunch or an early dinner at Midden by Mark Olive, House Canteen, or Opera Bar. Learn all about the Opera House from your guide, then relax and soak in the show-stopping views at your choice of restaurant.

Discover the joy of coming face to face with majestic humpback whales while cruising across the ocean on a sailing boat on this fun-filled tour from Sydney Harbour. Running between May and November, the annual whale migration is a sight to behold. This small-group sailing tour gives travelers the chance to cruise alongside these incredible creatures without noisy engines or megaphones, so you can enjoy an immersive and wild natural experience.

Be sure to put a performance by Opera Australia at the iconic Sydney Opera House on your Sydney itinerary. See classic operas by composers like Massenet and Verdi, as well as iconic Broadway musicals, depending on the season. Take in stunning views of Sydney Harbour while enjoying drinks or a meal (own expense) at one of the Opera House's fine dining venues before or after the performance to top off this unforgettable experience.

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.

In this private small group Walking Tour 'Discover The Colony' we will travel back in time to discover all the secrets of the birthplace of modern Australia by visiting The Rocks Historic District and the Sydney Royal Botanic Gardens. We will also cover the main projects that make Sydney a unique modern city. The tour guide will run the tour exclusively for you or your group (up to 10 guests). This is a very intimate experience to make you really enjoy the rich history of the oldest neighbourhood in Australia. In the first half of the tour, we will walk the cobblestone alleys of The Rocks where we will tell the stories of the first convicts, prostitutes and gangsters. We will understand what were the true interests of the British Crown to create a penal colony in Australia, and we will relive the terrible living conditions of this first settlement. We will continue our adventure walking to the Sydney Royal Botanic Garden to discover the historical importance that this place has had in the development of the penal colony and for the Aboriginal communities. We will visit the Sydney Opera House forecourt to learn all the details of its construction.

Celebrate Christmas in July on board a 3-hour Sydney harbor cruise. Enjoy live entertainment, win prizes for the most ridiculous Christmas sweater, sit down for a full Christmas buffet feast with roast turkey, seafood, pudding, coffee, tea and desserts, and capture it all with a photographer on board. Get into the spirit with Christmas décor and crackers on each table and see the sights from the ship’s exterior decks.

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.

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 beautiful Sydney Harbor on a Christmas Day cruise. Take in picturesque views of the city skyline while your favorite holiday tunes hum in the background. Enjoy a delicious buffet meal of seafood, traditional roasts, salads, and dessert—it’s included in the tour price—as well as fresh coffee and tea. Add to your merriment with alcoholic beverages from a fully licensed bar at an extra charge.

Hop aboard an authentic tall ship for an Australia Day to remember. Celebrate Australia’s national day on the annual Tall Ships Race on Sydney Harbour. Tuck into an Aussie-style lunch as you whip past the Harbour Bridge and Opera House. Make the most of unlimited beer, wine, and soft drinks to get you in the celebratory mood. You even have the chance to climb the mast, if you’re feeling adventurous.

In this private walking tour, we will explore the picturesque historic sites of The Rocks. This area is the birthplace of modern Australia, and any tour of this city should start here. The tour guide will run the tour exclusively for you or your group (up to 10 guests). This is a very intimate experience to make you really enjoy the rich history of the oldest neighbourhood in Australia. We will reveal how Britain created a penal colony on the other side of the world and what the first convicts found when they first arrived. We will explore hidden cobblestone alleyways to unveil the harsh living conditions of this first settlement. We have tons of fun anecdotes to bring this historic district to life. Sydney Harbour is the perfect background for this tour, and we will explore all the secrets behind the two major projects that have put Sydney on the map, the Sydney Harbour Bridge and The Sydney Opera House. The starting time is 18:00. Please get in contact to organize a private tour at a different time (min 6 guests).

The landscapes of Blue Mountains National Park are often explored from lookouts—but the waterways offer a quieter perspective. This leisurely lunch cruise aboard a restored paddlewheeler follows the Nepean River through the dramatic Nepean Gorge, whose sandstone cliffs date back millions of years. As you drift along the river, enjoy a two-course lunch with coffee and tea while taking in the scenery and chatting with the captain if you wish.

Eat and drink some of Australia’s finest produce on this delicious day tour to the Hunter Valley from Sydney. As well as tasting locally made wine, chocolate, cheese, vodka, and gin, you’ll learn about how these are made, and witness artisanal production techniques. You also won’t have to worry about appointing a designated driver, as you’ll be driven around so all travelers can relax and enjoy themselves.

Discover the Hunter Valley with a WSET certified wine host on a private experience curated entirely around you. Before your tour, we'll get to know your favourite wine styles, interests, and travel preferences, then personally design an itinerary to match. We'll select wineries that suit your palate. Your day includes private return transport from your Sydney hotel, premium wine tastings, a gourmet Australian savoury pie and wine pairing, and time to explore the historic Wollombi Valley. How it works: 1. Reserve your date Book your preferred day and secure your private Hunter Valley experience. 2. Tell us what you love We'll personally contact you to learn about your favourite wines, interests, and the kind of day you'd like to have. 3. We create your perfect day We'll curate a personalised itinerary with wineries, tastings, and experiences chosen just for you. 4. Relax We'll collect you from your Sydney hotel and take care of everything from there.

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.

Balmain’s pub scene is packed with history—but without local insight, it’s easy to miss the stories behind the bar. On this guided walking tour, visit several of the neighborhood’s best-known pubs and enjoy a complimentary craft beer or wine at each stop. As you stroll between venues, your guide shares tales of colorful characters and working-class roots that earned Balmain its reputation as one of Sydney’s original “puburbs.”

Bespoke Cycle Tours specialize in small group interactive tours particularly for mature age travelers. Locations incl. Sydney, regional Australia, Sweden and Italy. This 17 km leisurely Sydney e-bike ride for 2-4 people will give you a wonderful insight into the natural and built history of Sydney with an experienced local guide. Ride primarily on bike pathways around the iconic Sydney Harbour and through some beautiful but lesser-known waterside parklands. Cross the Sydney Harbour and ANZAC bridges and experience the vibrancy of Darling Harbour. Time to enjoy coffee and a leisurely lunch; your choice of the Sydney Fish Market or a trendy café popular with the 'locals'. Price also incl. entry to Aust. Maritime Museum or S.H. Ervin Gallery. E-bikes are high quality Moustache step through design with a comfortable seat and suspension.

Get out of Sydney for the day on an indulgent winery tour of the Hunter Valley. Head north of the city in a comfortable mini-coach without the hassle of driving yourself (or having to designate a driver who can’t drink). Visit three cellar doors, where you’ll sample some top local wine. Also get the chance to sample locally made chocolates and cheese, for a full culinary experience.