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Pilgrim Sailing

522 New South Head Rd, Woollahra, Sydney, New South Wales 2028, Australia
+61 424 296 406
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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 favourites is the Twilight Racing on Wednesdays and Fridays. You can jump on board a beautiful 58-foot yacht and either relax & enjoy the stunning harbour at sunset or be part of the crew and help sail the boat (instruction provided). Or if you'd rather a relaxed harbour cruise, come for a gentle sail on Sydney Harbour and soak up the views over the city as the sun goes down. Enjoy a selections of wines, beer and cheese as we sail from Rose Bay to the Sydney Harbour Bridge and Opera House. Alternatively charter Pilgrim for an exclusive cruise on the harbour - sailing, swimming, lunch, whatever you wish! Pilgrim Sailing provides the yacht, skipper and crew, prepares your food and is also happy to teach you to sail.
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Travelers talk about
Open Now
Hours
Hours Today: 9:00 AM - 5:00 PM
Suggested Duration: 2-3 hours
LOCATION
522 New South Head Rd, Woollahra, Sydney, New South Wales 2028, Australia
Double Bay
CONTACT
Website
+61 424 296 406
Ways to Experience Pilgrim Sailing
from $82.30
More Info
Write a ReviewReviews (51)
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"sydney harbour"
in 16 reviews
"an amazing experience"
in 5 reviews
"great hosts"
in 3 reviews
"sailing experience"
in 3 reviews
"an experience not to be missed"
in 2 reviews
"family and friends"
in 2 reviews
"beautiful boat"
in 2 reviews
"a great evening"
in 2 reviews
"magnetic island"
in 2 reviews
"icing on the cake"
in 2 reviews
"sailing boat"
in 2 reviews
"feel welcome"
in 2 reviews
"rose bay"
in 2 reviews
"great value"
in 2 reviews
"paul"
in 35 reviews
"crew"
in 20 reviews
"twilight"
in 12 reviews
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1 - 10 of 50 reviews

Reviewed April 27, 2018 via mobile

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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed March 22, 2018

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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed January 22, 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded January 23, 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!

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Reviewed January 21, 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed December 22, 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded January 23, 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!!

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Reviewed December 9, 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded January 23, 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!!

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Reviewed November 25, 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded January 23, 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!

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Reviewed July 11, 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded October 28, 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

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Reviewed July 9, 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
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded October 28, 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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Reviewed April 11, 2017

We spent 10 days in Australia and our entire family agrees that our sail on the Pilgrim was the best day of all. Clare was so helpful in booking both by email and phone. Once we arrived on board both Paul and Clare were welcoming,...More

Thank mijosmom
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded April 17, 2017

Thank you for your kind review. We loved having you guys on board - was such a fun day on the harbour for us too. We're delighted you enjoyed the food and the trip. Hope to see you on board if you ever visit Sydney...More

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Nearby
Double Bay
Located in Sydney’s eastern suburbs, Double Bay is a
one of the city's most beautiful harbor neighborhoods.
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 restaurants, late night bars,
...More
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