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Open today: 9:00 am - 5:00 pm
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Pilgrim Sailing offers everyone an opportunity to enjoy sail on Sydney Harbour and enjoy the beautiful views of the Sydney Harbour Bridge, Sydney Opera House and the harbour foreshore during the summer months (November to March). One of the...more
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Hours Today: 9:00 am - 5:00 pm
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Suggested duration: 2-3 hours
522 New South Head Rd, Woollahra, Sydney, New South Wales 2028, Australia
Double Bay
+61 424 296 406
Ways to Experience Pilgrim Sailing
from USD 81.10
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Reviews (52)
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All reviewssydney harbouran amazing experiencemagnetic islandsailing experiencefamily and friendsa great eveningicing on the cakebeautiful harboursaladpaulcrewtwilightracepilgrimsskiingboatsip
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1 - 10 of 51 reviews
Reviewed 1 week ago

My six year old daughter and I had a fantastic time sailing last week on the Pilgrim at Magnetic Island. Claire and Paul are lovely hosts and very welcoming to families with kids. The lunchtime cruise is a great choice of cruise for families. We...More

Thank Eleanor B
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 1 week ago

Thank you for you review - we’re delighted you enjoyed our lunchtime cruise! They are a great way to spend a few hours on the water and get to explore some of the hard to access bays on Magnetic Island. Hope to see you on...More

Reviewed 28 April 2018 via mobile

Absolute gem on a perfect evening for a sunset sail. Claire & Paul are fantastic hosts, the cheese platters phenomenal, sunset beautiful. Highly recommended trip, of all the boat trips I've taken for sunsets over the past 2.5years (and that's many) this is my favourite....More

Thank mazza_1919
Reviewed 23 March 2018

A wonderful sailboat experience (my first). It was so much more comfortable than I was expecting and since they limit the number of people on the boat it was like having our own personal trip. The cheese and wine were both wonderful - Claire and...More

Thank Kathleen H
Reviewed 23 January 2018

We had absolutely fabulous time with Claire and Paul on sip and sail sunset cruise. I bought it as a birthday gift for my wife and she loved it. This is such an amazing experience for couples whether you are local or visitor to sail...More

Thank MateuszP
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 24 January 2018

Thank you MateuszP. We are so pleased you enjoyed the Sip&Sail - it is a beautiful way to spend an evening! Please join us again - maybe for a Twilight Race, another unique experience on the Harbour!

Reviewed 22 January 2018 via mobile

What a wonderful way to experience Sydney Harbour aboard Pilgrim. Paul and Claire are such wonderful hosts and make you feel completely at home on board. Highly recommend to anyone looking for a unique and memorable experience.

Thank Halagram
Reviewed 22 December 2017

A great evening sail - strong winds in the harbour saw a flying start for Pilgrim. Claire and Paul had the team and the boat ship shape and on winning form! A really fun and upbeat crowd on board, with a mixture of sailing experience...More

Thank Alice C
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 24 January 2018

AliceC - thank you! It was a GREAT race!! Always good to win!! We're so pleased you enjoyed the night and hope you'll join us again next time you're in town!!

Reviewed 10 December 2017 via mobile

We had the best time sailing with pilgrim sailing. Paul and Claire are a phenomenal team showing the ropes of sailing, showing us Sydney harbour and serving us delicious wine and cheese. We really had the best time and would recommend this adventure to everyone....More

Thank helen1007
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 24 January 2018

Thanks helen1007 - we loved having you and your Dad on board. It was a beautiful evening with heaps of fun. Thanks for recommending us - we really appreciate it! See you on board again, we hope!!

Reviewed 25 November 2017 via mobile

Our experience on Pilgrim was fantastic and full of fun and laughs. We participated in a twilight race on a beautiful, sunny Wednesday evening, my 2nd time out and my friend’s first. Great fun to get involved! Paul and Claire run a tight ship (pardon...More

Thank AmyMichelle86
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 24 January 2018

Thanks for your review. Twilight racing is heaps of fun and we do encourage guests to get involved, with the support from the crew! Hope you will join us again before the end of the season!

Reviewed 11 July 2017

Picture this; a July Sunday afternoon, sun is shining, water is 23 degrees and we step on Pilgrim to enjoy our afternoon sail and hand Claire and Paul our bag (filled with champas, wine and beer) and that was the last time we touched the...More

Thank Matt J
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 29 October 2017

Thanks, Matt J. It was a great day on the water and always good when the wildlife comes and says hello! The lunchtime cruises are a perfect way to relax and see some of Magnetic Island and of course enjoy a sail on Pilgrim too!...More

Reviewed 9 July 2017 via mobile

We spent an incredible day with Paul and Claire on their amazing 58ft yacht on Magnetic Island. Food was fantastic. Service rivaled any experience based tour i have been on anywhere in the world. Would find the boat in Sydney in Magnetic or Sydney again...More

Thank jamesdiamond123
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 29 October 2017

Thanks, James! It was so good to have the family out for the day. We're delighted you loved Pilgrim - we think she's pretty unique! Hope you can join us again in Sydney or Maggie!

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Double Bay
Located in Sydney’s eastern suburbs, Double Bay is a
one of the city's most beautiful harbour
neighbourhoods. Designer boutiques provide a decadent
shopping experience and dress some of the most
beautiful people in Sydney. Sit down at one of the
open air cafes for a latte or a meal and enjoy the
people-watching. Double Bay was once an exclusive
enclave for an older, elite population, but new
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