2026 Date Wish List

2026 Date Wishlist

From intimate nights to luxurious international escapes, take a look at my dream date ideas in Sydney, Melbourne and beyond in 2026.

From intimate nights to luxurious international escapes, take a look at my dream date ideas in Sydney, Melbourne and beyond. 

If we have already connected, you will know I appreciate life’s finer things, like interesting wines, delicious food, stunning settings and silk sheets. Add some touches of adventure, exotic or beautiful locations and a luxury hotel room (all the better if there is a hot tub), and you’re describing my dream date or weekend getaway. 

2026 is now on its way, and I have put together a list of my ideal destinations and outings in Sydney, Melbourne and beyond. I’ve shared my ideas for a full day together, an evening experience or a fly me to you adventure. 

Take a look, then let’s find some time to spend together. 

 
Reserve a future date
 

Sydney Wish List

I’m a Melbourne woman, but Sydney’s harbour, nightlife and scenery never fails to impress me.

SYDNEY DATE ideas 2026

For the evening

Aria Restaurant & The Crown Hotel

The Sydney Opera House is iconic and I could stare at it for hours. Last year I visited Bennelong Restaurant but you can’t see the Opera House when you’re inside it. This is why Aria is on my list; it has the view.

Being from Canada, you’ll understand it’s always a joy to see Sydney Harbour and I’m excited to share an evening by the harbour with you.

After dinner (and maybe a show?), we can head back to the stunning Crown Towers to take in sweeping views of the city skyline. 

A night at the Ballet

I love the ballet and have tickets to the Melbourne season every year, but The Nutcracker will be performed by the Australian Ballet at the Opera House at the end of next year. I love Christmas, ballet and the Opera House, so this date night would tick every box. 

 

For the day

Private Yacht Charter on Sydney Harbour

If we have more time, let's book a private charter on the waters of Sydney Harbour. If it’s a warm and sunny day, we can take a dip and relax on board with a spread of sumptuous seafood and some chilled Champagne. 

Local providers offer full or half-day cruises, and there are so many gorgeous vessels to choose from. 

For the weekend

Hunter Valley Escape

You know I like to spoil my senses and the Hunter Valley is a good place to do this.  It is most famous for its Semillon, which is rare to find in Australia not blended with something else. I would love to visit this region and taste what it has to offer.

Let’s hire a luxury car to make our way up the freeway, spend the afternoon exploring and wine-tasting, then spend the night somewhere amazing. There is no shortage of five-star places to stay and we will be spoiled for choice when it comes to restaurants as well. 

 

Melbourne Wish List

Melbourne is Australia's cultural capital and this is where I’m right at home. From modern architecture to parks and laneways, there is always something to explore. Let’s immerse ourselves in the city’s thriving arts scene, dine at renowned restaurants and discover the best bars together.

 

MELBOURNE DATE IDEAS 2026

For the evening

Private Yarra Cruise

Let’s get away from the crowds with a private cruise on a warm summer evening. There will be no distractions as we relax and enjoy each other’s company.

Afterwards, we can head to The Ritz-Carlton and look down on the lights of the city from this stunning high-rise spot. 


For the day

Melbourne Grand Prix 

I’ve never had the chance to experience the Grand Prix in Melbourne and this is definitely on my wish list. 

There’s something so exciting about those powerful machines! So many of my girlfriends have told me this is not to be missed and I’m looking forward to understanding what the hype is really about. 

If we find accommodation nearby, we can follow our own itinerary, watch all the action and escape the crowds for some peace and quiet as soon as we’re ready.

 
 

For the weekend 

 Explore the Coonawarra Region

Victoria’s stunning coastline beckons… 

I am a serious wine lover and have always wanted to explore the Coonawarra Region on the Limestone Coast because I am a huge fan of the blends this region produces. 

We can travel by car or both fly into Mount Gambier and use it as a gateway to explore the area. Let’s find a secluded and cosy holiday cottage with an open fire and hide ourselves from the world once we have chosen a couple of bottles of cabernet to take home. 

 

BIGGER ADVENTURES

While we are on the subject of dates for 2026, I have a few more ideas for my bucket list that include spots I would love to explore as part of a Fly Me To You experience. These weekends (or weeks) stand out on my calendar because I have the opportunity to really get to know my travel partner, and we have so much time to relax and enjoy each other’s company. 

We could treat ourselves to an amazing adventure at one of the following places: 

 

Hamilton Island

Hamilton Island and The Whitsundays are my dream destination and will always be on my wish list. 

Let’s head there in 2026 for sun, cocktails, restaurant dining, afternoon swims and beautiful sunsets. 

Skiing in New Zealand or Japan

If you’re keen for a bit of adventure, let’s travel together to a snow-filled destination. 

I’ve heard so much about Queenstown and I’d love to experience it for myself, but we could also travel further afield and visit the slopes in Japan. 

After a long day of skiing or snowboarding, we can get cosy… I promise I’ll keep you warm!

 

Fiji

Warm waters, white sand, fresh food and local hospitality… what’s not to love about Fiji?

The best resorts offer private bure accommodation or adults-only wings with Infinity Pools and added extras like spa treatments. We can book some cultural experiences, outdoor activities or sightseeing adventures, or simply relax and enjoy our gorgeous accommodation.


Hong Kong

Hong Kong blends energy and elegance in the best possible way, and it feels perfect for a Fly Me To You escape where we can experience something different together.

We can spend our visit exploring vibrant neighbourhoods, hidden cocktail bars and world‑class shopping, then slow things down with a harbour cruise followed by rooftop drinks and long dinners overlooking the skyline. 

It’s a destination where we can dress up, indulge, talk for hours, and really enjoy the rhythm of being away together with equal parts excitement and intimacy.

About your date

Nice to meet you, I’m Olivia

I’m fabulous and forty, and the only thing I like more than the finer things in life is sharing them with someone special. 

Let’s travel somewhere together or enjoy an evening on my home turf in Melbourne and get to know each other. 

I know you like the good life… I’m excited to experience it with you. 

The best encounters have a combination of divine surroundings, tantalising food and wine, once-in-a-lifetime experiences and genuine company. 

These are just a few of the date and travel ideas on my wishlist for 2026, but I’d love to know what you have in mind as well. 

Spoil me and I’ll spoil you back! 


When you are ready, email reservations@oliviawinsome.com and let’s schedule our connection.

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