DARLING HARBOUR, SYDNEY  -  Phone: +61 2 9280 1110 - [email protected]

Experience Your Unforgettable Romantic Sailing Trips with Sydney by Sail!

Imagine escaping from the busy city life to enjoy the romance of Sydney Harbour with your loved one.. Sounds dreamy, right? 

That’s why sailing trips are the perfect way to find solitude and seclusion, making them ideal for honeymoons and other romantic getaways. 

Sailing is the perfect way to unwind, bond, and enjoy unique moments together. Taking to the sea in some of Australia’s most stunning and unique spots is a once-in-a-lifetime experience made all the more memorable when shared with your loved ones. Sailing trips and a romantic overnight stay can be a wonderful option for couples seeking a romantic weekend getaway.

It may be difficult to spend quality time with your significant other during the week. Therefore, you should take time to plan special date nights in the best way possible. Taking a mini-yacht vacation serves as an excellent opportunity to unwind together and forget about the pressures of city life. A romantic getaway for couples, Sydney Harbour and its magnificent views are the ideal setting for a wide range of activities.

A sailing trip with your partner should be a time to unwind, unburden, and simply enjoy each other’s company without any worries or concerns. When you book one of Sydney by Sail’s sailing packages for couples, our seasoned skipper will see to your every need, to and from your anchorage – no previous sailing experience necessary. 

With a luxury yacht charter and a well-planed itinerary, you are bound for an unforgettable date night! Sydney By Sail provides the newest fleet of luxury yachts for you to enjoy a romantic overnight stay with your partner. 

All you need to do is just bring an overnight bag stocked with the essentials (toiletries, clean underwear, a change of clothes, your favourite shoes, some tunes, and any alcoholic beverages you wish to enjoy). We have gourmet food platters for Dinner & Breakfast included for you, of course!

Where to go for a romantic Weekend Getaway 

The stunning Sydney Harbour is the perfect destination for your romantic weekend getaway. 

Set sail on Sydney Harbour with Sydney By Sail. You can either experience sailing the yacht by taking the helm and learning the ropes – or simply sit back and relax as your skipper guides you around the sights and sounds of historic Sydney harbour. 

Since getting on a yacht is like taking a mini-vacation all by itself, there are a plethora of things to think about, such as what to bring and what to pack for the ship. Because of this, here are some tips to make the most of your sailing trip!

Eating the right meals

An important aspect of any successful romantic getaway is the food. After a long day, it would be nice to relax and unwind by eating dinner together while chatting about the day’s events and watching the sun go down over the harbour. 

With Sydney by Sail’s expertly-designed catering menu, you will surely be in for a treat! Our packages include gourmet catering, with share platters of cheese & fruits, seafood, vegetarian antipasto or provincial meats, lunch boxes of classic healthy meals or international dishes such as a Mediterranean feast, a variety of delicious salads, choices of delectable breakfast boxes, and more! We also provide vegan and vegetarian food options to suit all your dietary needs. 

You can check out all of the delicious menu items we offer here

If you prefer to bring your own food, we’ve got you covered! Sydney By Sail’s yachts are also fully equipped with a stovetop and oven, as well as utensils, plates, and bowls.

If either you or your partner tend to become seasick, you should simply take some preventative medication. 

Leave room for the unexpected

While it’s always best to be prepared, it’s also important to accept that we may not always be able to prevent every unforeseen event. Boarding could be delayed, for example, if you are running late. 

In terms of weather conditions, rest assured that Sydney by Sail will never send you out in weather that is considered dangerous, such as really strong winds or thunderstorms. If there were some showers forecast on the day of departure, the experience will still continue, but you could get a free upgrade to a larger boat or we could arrange an early start or late finish for you. Nonetheless, as you are spending the evening on a state of the art luxury yacht, having some light showers during the experience only makes things more cosy and comfortable as you are lazing below decks.

Being adaptable might help you have a good time with your partner regardless of what comes your way! 

Keeping it simple

Last but not least, the phrase “less is more” also applies here. A romantic getaway is all about you and your significant other. The yacht’s harbour makes for a stunning photographic backdrop, and the yacht’s tranquil environment is perfect for striking up conversations with each other. 

Another piece of sound advice is to put away your electronic gadgets for the day so that you can focus on each other. Reconnect with one another and make up for any missed time in your busy schedules by taking a break on our luxury romantic b&b packages. 

What to do on a romantic getaway? 

When you sail with us, we will use our 27+ years of experience sharing Sydney Harbour by sailing boat to make your experience unique and unforgettable. Our in-depth knowledge of Sydney harbour means we can provide many suggestions on where to go and drop anchor for a swim, where to sail to get the best wind and the best angles for a photo of you and your loved one. 

With our Platinum B&B Package, get a taste of Sydney Harbour, as you sail past the big POI’s (Sydney Harbour Bridge & Opera House), around Bradley’s head and towards the more exotic Chowder Bay & Watsons Bay. View the vast sea beyond the Heads as you make your way to a safe harbour for the night.

With our Gold B&B package, you can also take a cruise around the Harbour’s most picturesque spots. Pass beneath the Harbour Bridge and the Opera House, then sail around Shark Island to your sheltered bay for the night.

If you want to get a full day of exploring Sydney Harbour, opt for our Diamond B&B packages. Sail past the big POI’s (Sydney Harbour Bridge & Opera House), around Bradleys Head past the entrance to Sydney Harbour to the promised land – Manly Bay. Settle up in Quarantine Cove for lunch and a swim, or discover Middle Harbour’s hidden coves and bays. Within 6 hours, you can do just about anything! 

Our Romantic B&B Packages will certainly impress your loved one – enjoy a sightseeing cruise with a private skipper guiding you about Sydney Harbour, followed by an overnight stay unaccompanied onboard a luxury yacht, with gourmet catering for all meals included.

Give your loved one the gift of a lifetime by giving them a taste of the high life aboard a luxury boat in Sydney Harbour.

Other Activities You Can Do With Our Top-Notch Sailing Services

There’s no better way to experience nature than going on a sail trip. Whether you’re on a weekend getaway with friends, family, or a romantic trip with your partner, sailing is perfect. Imagine harnessing the power of the wind to skillfully navigate Sydney harbour on a luxury yacht!

The tranquillity and breathtaking scenery of a sailing vacation is a refreshing break from the stresses of daily life. And it’s a delightfully luxurious way to enjoy the outdoors, since you never have to pitch a tent and you always have a warm bed at your disposal. This is the time to put down your phone, close your laptop, and take in some fresh air and natural beauty without any distractions.

With Sydney by Sail, you can use our sailing services for purposes such as: 

    • Team-building. Sailing helps you learn about how to build team cohesiveness. Team building events are a great way to inspire team cohesion and facilitate stronger workplace relationships. Our team building activities are engaging, safe, and entertaining since they involve face-to-face interaction while sailing on luxury yachts in the beautiful Sydney Harbour. Have a look at the packages we offer here
    • Private yacht charter. We have the newest fleet of luxury sailing yachts available to domestic or international guests who wish to witness this stunning Harbour while under sail – harnessing the wind to explore and adventure. Guests can take the helm at any time with no prior experience required, or they can sit back, relax, and let the experienced skipper lead the way as they cruise the Harbour. Learn more about it here
  • Sailing school. Get certified with our internationally accredited Sailing School. All of our instructors are professional yachtsmen with appropriate licences. Many participants have completed long-distance ocean voyages and international sailing events, such as the Sydney-Hobart Yacht Race. Find out more about our courses here.
  • Coastal sailing or whale watching. A unique combination of sailing and whale watching off the coast of Sydney Harbour. Out the heads, it is likely to see all kinds of marine life, like dolphins, seals, turtles, sharks and during the right time of year, Whales!
  • Daily sailing trips. Discover Sydney Harbor on a three-hour sailing adventure, the most enjoyable way to view the harbour. Learn the basics of sailing while taking in the views. You may either take the wheel and learn the ropes or sit back and enjoy the ride as your skipper takes you around beautiful Sydney Harbour.


Sailing getaways offer the potential for both adventure and relaxation. The point of going on vacation is to kick back and have a good time, right? One surefire way to achieve that pinnacle of happiness is by embarking on a fantastic sailing trip.

Take a look at what we offer by exploring our site more. You can also view several videos on some of our different yachts such as the Hunter 36, Dufour 412 and Elan Impression 45.1.  

Smooth Sailing with Sydney by Sail!

A sailing vacation is the perfect way to unwind and leave your worries behind for a while. You are free to choose what you want to do, eat and how you spend your day. It’s a breather from routine and the stresses of life, and the opportunities it presents are limitless.

At Sydney by Sail, we will arrange a worry-free holiday for you and your loved one. Relax and take in the sights on the water while we plan the rest of your sailing trip. To ensure a stress-free and enjoyable sailing experience, we will answer any concerns you may have concerning the itinerary, logistics, activities, safety precautions, and crew members.

Worry of getting seasick? We always choose the best possible sheltered anchorage to minimise the rocking of the yacht. Occasionally during the night wash from passing vessel might cause the yacht to rock. If you are susceptible to seasickness or travel sickness you can try remedies such as tablets, spray and wrist bands. You can check out our Frequently Asked Questions page for more information . 

Discover the many luxury sailing yachts we have and let us know if you’re interested in joining us on an exclusive yachting adventure.

If you are unsure and need some help, please do call us on +61 (2) 9280 1110 or simply send us a form through our contact page, we are always happy to help. Book your trip now!


Experience the lifestyle and luxury of yacht life on Sydney Harbour with Sydney By Sail.


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National Maritime Museum
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Darling Harbour NSW 2000
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