Sip and Sail Twilight Cruise on Sydney Harbour

Sydney Harbour departing Rose Bay
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$149 each
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  • Two hour sunset cruise on board a beautiful 58 foot sailing yacht
  • Sail under the Sydney Harbour Bridge, past the Sydney Opera House and soak up views of the sun setting over the city
  • Enjoy tasting a selection of Tamburlaine Organic Wines or craft beers and a delicious local cheese platter

Set sail aboard a beautiful 58-foot sailing yacht for a memorable twilight cruise on Sydney Harbour. Enjoy some local organic wines or beer accompanied by a gourmet cheese platter while you sail past the Sydney Opera House and under the Sydney Harbour Bridge.

What's Included?

  • 2 hour sunset sail
  • Selection of Tamburlaine Organic wines, Great Barrier Beer or other beers and soft drinks
  • Delicious cheese platter with accompaniments
  • Personal and intimate experience with up to 16 guests on board
  • Experienced, professional and friendly hosts
  • Full safety briefing

Your sunset sail begins at Rose Bay, Sydney where your hosts for the evening Clare & Paul will welcome you aboard a beautiful 58-foot sailing yacht, Pilgrim. After a full briefing to ensure all guests feel comfortable and safe Pilgrim 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 different Tamburlaine Organic Wines on board (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.

Session Length

  • Arrive at Rose Bay Public Wharf at 5:30pm
  • Vessel will pick you up at 5:45pm (sharp)
  • Returns to Rose Bay Public Wharf by 7:45pm (approximately)
  • This experience runs every Saturday from 11th November until early March


  • Participants must be aged 18 years or above to be served alcohol; photo ID may be required


Once this experience has been confirmed, changes are at the discretion of the experience provider and arranged directly with them according to their policy.

Numbers on the Day

A minimum of six guests are required for this cruise to proceed. If minimum numbers are not met, the sailing will have to be rescheduled.


The skipper will make a decision at 3pm on the day if cancellation is required due to weather.

Dress Code

Please wear: Flat white soled shoes (no heels or black soled shoes permitted), comfortable clothes, spray jacket, something warm (just in case). If you are wearing unsuitable shoes you will be asked to remove them.

Other Info

Seasonal operator in Sydney from November to March each year.

This experience takes place on Sydney Harbour departing from Rose Bay.