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Pilgrim Sailing

U 14 522 New South Head Rd, Double Bay, Woollahra, New South Wales 2028, Australia
+61 432 297 911
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USD 80.26*
and up
Sydney Harbour Sip and Sail Twilight Cruise
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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). A summer favourite is the twilight racing on Wednesdays and Fridays. For only $99pp 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. You'll receive a complimentary glass of sparkling wine or bottle of beer to enjoy as we cruise from Double Bay to the Sydney Harbour Bridge and Opera House. (Only $99pp) 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. Charters available from 2 hours and start at $75pp.
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Open Now
All hours
Hours Today: 10:00 - 20:00
Suggested Duration: 2-3 hours
LOCATION
U 14 522 New South Head Rd, Double Bay, Woollahra, New South Wales 2028, Australia
Double Bay
CONTACT
Website
+61 432 297 911

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Reviews (44)
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1 - 10 of 43 reviews

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
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
Reviewed 12 April 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
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 18 April 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

Reviewed 28 March 2017

This trip was lovely clam relaxing sipping wine,and eating cheese and nibbles, what more can you ask for in the great sydney, harbour wonderful staff and hosts. Looking for something to do at the end of the day before hitting the town then this is...More

Thank Sue D
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 18 April 2017

We're glad you enjoyed the Sip&Sail and found it relaxing. That's what it's all about! Hope to see you on board again for another Sip&Sail or one of our other sailing trips!

Reviewed 28 February 2017

This was a great afternoon spent on the beautiful Sydney harbour. Wine and cheese included with a great bunch of people. Small sailing vessel (holds up to 24 guests I think). The crew were marvellous and couldn't do enough to ensure we had a good...More

Thank Karen58_11
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 18 April 2017

Great to hear you enjoyed the Sail. We take great pride in our service and ensuring everyone has a wonderful time and is well looked after. Hope to see you on board again soon!

Reviewed 7 February 2017

Paul, Clare and crew were absolutely fantastic - they made the Friday twilight racing such a happy and friendly opportunity to have a go at something new. We certainly recommend it to everyone - you meet interesting people, have fun, compete, and enjoy the exhilaration...More

Thank Amanda W
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 18 April 2017

Thank you for taking the time to post a review about your experience on our Twilight Racing. It's a fun evening out and is certainly different to your usual night out!!

Reviewed 4 February 2017

Clare and Paul are great hosts, and took our group on a lovely sail around Sydney Harbour with a lunch stop. The food they served for lunch was fresh and delicious, grilled right on the back of the boat. Highly recommended!More

Thank smyers802017
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 18 April 2017

Thank you for taking the time to review your charter. It was great to have you and your team/colleagues on board to experience Sydney Harbour on your visit to Australia. Hope to see you again if you're visiting Sydney again - maybe next time for...More

Reviewed 19 January 2017

As soon as you step on board, Clare and Paul, make you feel right at home, they welcome you with a smile, then cover a few safety tips and local knowledge. They make it quite clear that they are there to make your sail on...More

Thank Janet061
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 29 January 2017

Thank you for your feedback - we're delighted you enjoyed yourselves and thank you for helping out with the steering - it's always great when someone wants to get involved! Hope to see you on board again soon!

Reviewed 16 January 2017

Clare and her husband make everyone (even stowaways!) feel welcome and entertained throughout the sail. Highly recommended for both Sydney-siders and out-of-towners alike.

Thank Peter M
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 17 January 2017

Thank you for posting a review. We're delighted you enjoyed the #Sip&Sail and very pleased that we could fit your extra guest on board too! Hope to see you both out on the harbour on Pilgrim again soon!

Reviewed 15 January 2017

Clare and Paul gave us a wonderful experience on a genuine racing sailboat surrounded by the awesome sights of Sydney Harbour at dusk. Living in Florida USA and having been sailboat owners, we were looking for something more genuine then a "booze cruise" on an...More

Thank wdw56
ThePilgrimsofOz, Owner at Pilgrim Sailing, responded to this reviewResponded 29 January 2017

Thank you wdw56 - it was great to have you guys on board on such a beautiful night on Sydney Harbour. We take great pride in Pilgrim and our service so we're delighted you enjoyed yourselves. Definitely look us up next time you're in town....maybe...More

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