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Winston dancing with Teresa at Observatory Hill in Sydney

Observatory Hill Proposal Sydney - Winston and Teresa

Aug 24 2026 | By: Sarah Iris Photography

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Winston & Teresa’s Surprise Proposal at Observatory Hill, Sydney

A sunset proposal in the Observatory Hill gazebo

Winston had carefully planned a surprise proposal for Teresa at Observatory Hill in Sydney. He booked the gazebo and chose the timing to make the most of the beautiful evening light, with the Sydney Harbour Bridge stretching out behind them.

Then Winston got down on one knee and asked Teresa to marry him. 💍

Winston proposing to Teresa at Observatory Hill in Sydney

It was a lovely moment to capture, with the harbour providing a beautiful backdrop to the beginning of their next chapter together.

Winston proposing to Teresa at Observatory Hill in Sydney

After the proposal, we spent some time capturing the two of them together as the sun set over Sydney Harbour. 

Winston and Teresa together at the Observatory Hill gazebo after their proposal

Once the excitement had settled in, there were plenty of smiles, hugs and even some dancing together in the gazebo.

Winston and Teresa dancing in the gazebo at Observatory Hill

I loved photographing not just the proposal itself, but the moments that followed. The happiness, the excitement and the realisation that they were beginning a new chapter together made the evening particularly lovely to capture.

Winston and Teresa at sunset from Observatory Hill

A Sydney Harbour engagement session the following morning

The following morning, I met Winston and Teresa again for an engagement session around Sydney Harbour.

It was a little chilly, but Sydney was looking beautiful. We wandered around the harbour, with the Sydney Opera House and Harbour Bridge providing the backdrop for more photographs of the newly engaged couple.

Winston and Teresa with the Sydney Opera House during their engagement session

The morning session felt particularly meaningful because Teresa was preparing to move to Seattle. With such a big change ahead of them, it was lovely to have the opportunity to photograph them together in Sydney before they headed off on their next adventure.

Having both the proposal and a separate engagement session meant we could capture two different parts of their story, from the excitement of the surprise to a relaxed morning exploring the harbour together.

Winston and Teresa hugging with the Sydney Opera House behind them
Winston and Teresa looking at each other with the Sydney Harbour Bridge behind them
Winston and Teresa walking with the Sydney harbour bridge behind them
Winston and Teresa looking at each other with the Sydney Opera House behind them
Winston and Teresa at Sydney harbour
Winston and Teresa walking in a park with the Sydney Opera House behind them

Congratulations, Winston and Teresa!

It was lovely to meet you both and be part of such a special time in your lives. From the surprise proposal and dancing in the gazebo to our engagement session the following morning, it was a treat to capture these moments together.

Winston and Teresa dancing with the Sydney Opera House behind them

Winston and Teresa, I'm so excited for you both and your next chapter in Seattle. I hope you have an amazing adventure together and that your photographs bring you back to these beautiful moments in Sydney.

Winston and Teresa during a Sydney proposal photo session at Sydney harbour

Planning your own Sydney proposal

If you're planning a proposal in Sydney, choosing a location that feels right for you is a wonderful place to start. With more than 15 years of photography experience, I can help you plan the details so you can focus on the moment itself.

Whether you're visiting Sydney or planning locally, I'd love to hear what you have in mind.

Explore Sydney Proposal Sessions
A close up of a ring with the Sydney Opera House behind them

Together let's create memories to last a lifetime. ♡


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