#Sip&Sail Private - Sydney Harbour

From AUD $119.00
  • Duration: 120 Minutes (approx.)
  • Location: Rose Bay, NSW

Set sail aboard a beautiful 58 foot sailing yacht for a memorable sunset cruise on Sydney Harbour exclusively for you and your guests.

Enjoy some local organic wines accompanied by a gourmet cheese platter while you sail under the Sydney Harbour Bridge, past the Sydney Opera House and soak up views of the sun setting over the city.


  • 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.

  • Personal and intimate experience exclusively for you and your guests.

  • Enjoy a selection of Tamburlaine Organic Wines or Premium beer and a delicious cheese platter (other nibbles available too)


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.  

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, we have local Sydney brewery Young Henrys Natural Lager or Newtowner Pale Ale on offer along with Coronas and soft drinks.

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.  If you prefer we have different catering options available, which include antipasto platters, selection of canapés, Gourmet pie, sausage roll and quiches or a Prawn & oyster platter.

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.

Number of Guests:

Minimum booking is for 12 guests, maximum 18 guests.  If you have less than 12 guests, that's fine with us you will just be charged for 12 guests.


Available Tuesday, Thursday and Sunday evenings from November to March. Check the calendar for dates or contact us directly if you can't see your preferred date on the calendar.

Catering options 

We also offer a range of other catering options:

Antipasto Platter +$10 pp

Gourmet Pies, Quiches & Sausage Rolls  +$10pp

Selection of Canapes +$30pp

Oyster & Prawn Platter +$30pp

Select the "Upgrade to ..." options in the Extras section of booking.

BYO Option:

Note: If you prefer to bring your own drinks, nibbles and ice enter the code BYOSIPSAIL to receive a 20% discount. We do not recommend this for corporate events.


  • Board Pilgrim at Rose Bay at 5.45pm SHARP
  • Enjoy a selection of Tamburlaine Organic Wines (no red wines) or Great Barrier Beer
  • 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

Pick up/Drop off

Departing from Rose Bay Public Wharf, ROSE BAY at 5.45 pm SHARP.

Rose Bay Public Wharf is next to the Rose Bay Ferry Wharf, Lyne Park off New South Head Road.

Please arrive promptly so we depart the dock on time and don't keep other guests waiting.

Unfortunately, if you are late, the boat will have gone without you...

After the cruise Pilgrim will return to Rose Bay Public Wharf around 7.45 pm.

What to wear/bring

  • Flat white soled shoes 
  • Comfortable clothes
  • Spray jacket
  • Something warm (just in case)

If you are wearing unsuitable shoes you will be asked to remove them.


  • 2 hour sunset sail
  • Selection of Tamburlaine Organic wines or Premium beer or soft drinks 
  • Delicious cheese platter with homemade pumpkin chutney & accompaniments
  • Experienced, professional and friendly hosts to make your trip as enjoyable and memorable as possible