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Picture this: You and your sweetheart board a beautiful yacht. Together, you set sail for a cruise on the calm, glimmering waters of Sydney Harbour, breathing in the invigorating sea air. A fresh seafood dinner is under way, the champagne is chilled and you can feel the excitement of a night that you will remember and cherish for years to come. It sounds like a dream, but this could become your reality!

With spectacular scenery and great weather throughout the year – well, ok, most of the year – chartering a boat is a highly popular activity in Sydney. But of course Sydney harbour is also one of the world’s best backdrop for a proposal.

Here at Smart Cruiser Sydney, we love helping plan proposals and always feel so privileged to be able to somehow share an important part of our client’s life.

Through the year, we have came across some really fun and sometimes unusual proposal, and we have decided to share with you, 5 of our best recommendations. If you’re looking for a beautiful way to propose, we sincerely hope this helps!


  • Private, intimate Sydney cruise, on your own luxury boat

With well over 200 boats available for hire in Sydney, you are spoiled with choice and there is boat for everyone, regardless of your budget. Imagine yourself cruising beneath the spectacular Sydney Harbour Bridge, travel past the iconic Sydney Opera House and Luna Park and stop at historical landmarks like Cockatoo Island and Fort Dennison to propose.

Discover the timeless beauty of the harbour, and enjoy views of Sydney in a truly unique way. See places that cannot be accessed by land while of course enjoying a few glasses of Champagne with your partner. Why not ask your skipper to stop at a private and secluded beach, giving you the perfect opportunity to get down on one knee?

  • Adventure seeker: Propose 20 meters over Sydney harbour

This might surprise you a little bit, but it’s an incredibly fun and totally unique way to propose. You can now climb up the mast of a large Tall Ship, with your partner, and get on a viewing platform located nearly 20 meters over the water. A harness will be provided and all the safety gear that comes with it and you will have the time of your life!! And here is the best way of doing it:

– Hire a Tall Ship for 1 or 2H and have it ready and sailing under the Harbour Bridge

– Don’t tell your partner where you are going and jump on a water taxi
– Get the water taxi to drop you off on the Tall Ship
– Jump onboard and start the climb straight away – you will need to be a little bit fit, but I would say that 85% of people can do it, so it’s really accessible to most of us.
–  While at the top, enjoy the views, kiss your partner and ask the question – don’t drop the ring! 😉
– You will be able to stay up a few minutes and I can promise that you’ll remember this moment for ever; it’s awesome.
– Come down and enjoy the rest of your cruise, on your very own Tall Ship and witnessing the best views of the harbour with a Champagne in hand.

  • Hire your own private yacht for the entire night

If you don’t want to rush it, why not embark on a magical experience and stay overnight on your own private yacht? A skipper will cruise you nicely around the harbour, before stopping at a quiet location, where you’ll be able to enjoy a romantic dinner with the menu of your choice, as the city falls asleep. Enjoy the beauty of the sun disappearing behind Sydney harbour, and see the lights of the CBD rise around you. Some of the boats have 5 star accommodations with queen size beds and everything you would expect from a luxury hotel, with the addition of the gentle water flow under your bed.

The skipper will then leave you for the night, and will come and pick you up in the morning to bring you back to shore after a nice breakfast onboard.

This is a great way to truly celebrate and appreciate the moment, and it gives you time to ask the questions… when you are ready… I know from my own experience, that it is not always that simple. 😉

  • Propose with a backdrop of fireworks!

Surprise your partner with a romantic boat ride at sunset. We can help you make this a complete surprise, so you can jump onboard and start drinking champagne straight away. Of course you can have strawberries, roses, canapés… we can look after all this easily but what will really blow your partner way is this: Schedule your proposal for a Saturday evening and finishing at 9:15pm, so you have time to enjoy the spectacular 9pm Darling Harbour fireworks. It’s free, it’s fun and will undoubtedly add to the excitement, especially if you propose a minute before the fireworks start… Imagine how cool that would be? Is that not a pretty romantic way to propose?

  • Combine your cruise with a waterfront restaurant

Why not begin your proposal with a short sunset cruise, enjoying a glass of champagne before making a grand entry to your favourite Sydney waterfront restaurant? Some amazing restaurant destinations accessible by boat include Catalina at Rose Bay, Hugo’s at Manly wharf, Doyles at Watsons Bat or Wildfire at Circular Quay.

Another idea is to sit down for a drink at a water venue and organise a “surprise” cruise to come and pick you up. Contact us and we’ll help you create the “Wow” factor you are after.

Oh, and for the most adventurous of you, we recommend a quick cruise, seaplane toward Pittwater/Hawkesbury river and dinner at a waterfront restaurant up there. Talk to us for more details, we have tons of ideas that we will customize to your needs.

If you are ready to propose and want to do it in style, then contact us. We have the largest fleet of Sydney Harbour and we’ve helped hundreds of clients to find a perfect boat for their marriage proposals. They now have amazing engagement stories that they love sharing over and over. We would love to help, contact us today!