Sydney Harbour Sip and Sail Twilight Cruise

Duration: 2 hours
Destination: Australia, New South Wales, Sydney

Check Availability

  • 2 hours
  • Sydney
  • E-Voucher
  • Lowest Price
  • Non-Cancellable


Set sail aboard a beautiful 58 foot sailing yacht for a memorable sunset cruise on Sydney Harbour.  Enjoy some local organic wines accompanied by a a gourmet cheese platter while you sail past the Sydney Opera House and under the Sydney Harbour Bridge and soak up views of the sun setting over the city.

• Board Pilgrim at Rose Bay at 5.45pm sharp
• Enjoy a selection of Tamburlaine Organic Wines (no red wines), beer or soft drinks accompanied by a delicious cheese platter
• Pull out sail and enjoy the peace (wind permitting)
• Sail past the Sydney Opera House and under the Sydney Harbour Bridge
• Other sights can be included on request (time permitting)
• Watch the lights come up and the sun go down over the city
• Return to Rose Bay at approximately 7.45pm

Your sunset sail begins at Rose Bay, Sydney where your hosts for the evening Clare and Paul will welcome you aboard a beautiful 58 foot sailing yacht, Pilgrim.

After a full briefing to ensure all guests feel comfortable and safe you will head out into the Harbour and pull up sails. 

Pilgrim is the perfect yacht for a sunset cruise. She's stable and very comfortable with a large foredeck and two cockpits - so plenty of seating and space for you to spread out and relax.

The number of guests is kept to a minimum to ensure a very personal service to you - whether you want to learn about sailing, have a go a helming the boat or just sit back and relax.

On board there is selection of Tamburlaine Organic Wines (note: no red wine) for guests to enjoy. Alternatively if you’re a non-wine drinker, beer and soft drinks are available too.

There is also a selection of delicious cheeses and accompaniments to enjoy with your drinks as you relax and enjoy views of the Sydney Opera House, Sydney Harbour Bridge & other Sydney highlights.

Enjoy the peace as Pilgrim glides around the harbor while you watch the sun set over the city on the way back to Rose Bay.


  • GST (Goods and Services Tax)
  • Beverages - selection of Tamburlaine Organic Wines, premium beers and soft drinks
  • Light refreshments - cheese platter

  • Hotel pickup and drop-off
  • Confirmation will be received at time of booking
  • Children must be accompanied by an adult
  • Operates in most weather conditions, please dress appropriately
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
Departure Point

Rose Bay Wharf, New South Wales, Australia

Departure Time

5:30 PM

Return Details

Returns to original departure point

Voucher info

You can present either a paper or an electronic voucher for this activity.


2 hours

Package is not cancellable.

User's Reviews

Birgit S

08 Jan, 2020

Paul and Claire run the ship! What a great pair. Everything was so friendly and personable, making it one of our most memorable evenings in Sydney. What a delight to be on a working sail race boat. They involved our teenage sons and the other teenage girl in setting sail, which was really fantastic. It was relaxing and fun for us, a family of four, as well as the sweet honeymoon couple we met on board. Not at all like one of those overcrowded harbor cruises. We never felt crowded, cheese was beautifully paired with a homemade chutney, and wine and beverages were plenty. Claire took everyone who wanted up to the bow (of we could sit there too) for a perfect picture infront of the bridge and opera house, while Paul guided the boat so everyone got the best shots. That was a nice touch.

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