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The best way to experience Sydney Harbour is from the water and Pilgrim Sailing offers unique ways to do this suiting most tastes and occasions.  

​Pilgrim Sailing is owned and operated by Paul & Clare Ley who care about every aspect of your time on board - the well maintained & well presented boat, the welcome on arrival, the service on board, the quality of the food and wine and we always sail!

We promise we're not just another yacht charter operator on Sydney Harbour...come and find out for yourself!  
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​Only available from November to March each year.

FOR INDIVIDUALS, COUPLES AND SMALL GROUPS

Click here > For Larger Groups or Exclusive Hire of Pilgrim 

TWILIGHT RACING

Join the locals in an exciting yacht race around Sydney Harbour with up to 100 other yachts!

A different way to see sunset on the harbour!

Wednesday & Friday nights only

SIP&SAIL TWILIGHT CRUISE

​Join us for a relaxing sail on Sydney Harbour. Sail past the Opera House and under the Harbour Bridge with a sundowner in hand!

Sip, Sail & Dine package available.

Thursday & Saturday nights

LUNCHTIME SAILING CRUISE

Experience the magic of seeing all the iconic sights of Sydney Harbour from the water.

You'll also enjoy a delicious lunch and complimentary beverages.

Wednesday, Thursday, Fridays  (Jan-Mar)

SPECIAL EVENTS

 Catch all of the action of Sydney Harbour events over the summer on board Pilgrim.

On Boxing Day watch the Sydney to Hobart Race start or enjoy the festivities on 
New Year's Eve and Australia Day

FOR LARGER GROUPS OR EXCLUSIVE HIRE:

PRIVATE CHARTERS

Enjoy the exclusive use of a beautiful yacht.
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​Great for birthday celebrations, special occasions or to show off Sydney Harbour to guests in town!

CORPORATE ENTERTAINING

Share the best harbour in the world with clients or colleagues.  ​

A range of options to suit your needs and your budget.  From Executive Dining to Christmas events.

TEAM BUILDING

A unique range of team building events for four to twenty four guests.
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Get your team working together in a  twilight race or do some team bonding during a sunset cruise.

THE BOAT & US

Pilgrim Sailing is owned and operated by Paul & Clare Ley who care about every aspect of your time on board.

Every charter is hosted on Pilgrim, a beautiful 58 foot sailing yacht with beautiful lines and a great sailing pedigree.

LOCATION

From November to March each year Pilgrim Sailing is based in Rose Bay.

Our standard pick up/drop off is Rose Bay Public Wharf, next to the Rose Bay Ferry Wharf. For more information of this wharf and other pick up options: CLICK HERE

CONTACT US

Email us or call us with any questions on  0424 296406 or 0432 297911

CHECK OUT OUR SEASON HIGHLIGHTS FROM THE LAST FEW YEARS..

2017-18 HIGHLIGHTS
2016-17 HIGHLIGHTS
2015-16 HIGHLIGHTS​