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Sydney by Sail: Twilight Sailing

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by Justine Crowley (subscribe)
More of my written work, including my books: Runs the following sites:
Published April 22nd 2012
The Colorado ready to sail.

What am amazing experience sailing along Sydney Harbour, after the buckets of recent rainfall decided to settle down, on a glorious Thursday night. Really different to going on an organised comedy or dinner cruise, that's for sure. Thank you Sydney by Sail for what was an amazing sailing experience overall.

This was a recent reward from a Sydney based property consulting client, and so therefore I was sailing with a small group of people I work with. It was worth buying a pair of cheap slip ons with white soles (we were only allowed to wear footwear with white soles, otherwise our entire group would have been slugged an additional $100 for cleaning the boat).

Heading into the Festival Pontoon.

I felt a little sick prior to boarding the yacht due to the choppiness around the Maritime Museum (where we boarded our yacht, the Colorado) yet lo and behold, one of my fellow work mates is known for getting really seasick at the best of times in the water (thankfully we only stayed around Sydney Harbour) and was jokingly told to "bring a bucket" in advance just in case, and the whole group cringed when he ate some KFC beforehand.

Many of us (myself included) had no appetite prior to boarding the yacht whatsoever, and the great news was that nobody got seasick. The groups appetite all started to change the moment we all got really comfortable, and then the snacks came out of hiding, feeding around six hungry people. The size of the yacht (the Colorado) looked quite small, yet when all of us entered the yacht, there was just enough room for everyone. In no time at all many people from our group put their ponchos on real quick. I was (on the other hand) wearing something just as warm as a spray jacket.

One of my friends from work took (and wanted to take) a picture of me prior to boarding the yacht.

Beautiful Sydney Harbour on the Colorado.

Our designated skipper, Ramesh (an IT Consultant, originally from Sri Lanka, and who works part-time for Sydney for Sail) was rather friendly and experienced. Having worked for Sydney by Sail for the last four years, Ramesh is going for the tryouts to compete in the next Sydney to Hobart yacht race; we were in great hands, really great hands.

All aboard had a great time.

More Harbour views.

Just as the sails left Bangaroo, and headed towards Luna Park, things started to become interesting, and the tide was rather choppy, and I became the designated driver of the yacht while Ramesh got to chill out and check up on me every now and then, while I had to hoist the sails. Nervous at first, initially the group were making fun of me, but a few minutes later, they starting commenting that "I am a pro at sailing", which was comforting as I realised that I was armed with the responsibility of looking after the lives of eight people.

What a real buzz to be driving a yacht, right underneath the Sydney Harbour Bridge (and also the Harbour city) in darkness. Something I have never done before, not even in the 29 years I lived in Sydney prior to re-locating to Melbourne. I called a couple of my friends afterwards to tell them the great news.

Me driving the yacht.

Driving the sailboat was all well and good, until I got to Vaucluse and I wanted to take a bit of a break. I literally did the lions share of the sailing for half the trip, and then two more people shared the driving until Ramesh drove us back to shore, towards the end of this two-hour twilight sailing experience.

The rest of the group were chatting and kind of behaving like princesses (in comparison to those of us who actually drove the yacht), munching out on chips and dips, grapes and peanut M&M's.

A bit of concentration was required as there was an abundance of Manly ferries that were too close to comfort for me at times while driving. Thankfully our group was safe, despite the safety demonstration prior to the start of the Twilight Sailing experience (it got dark real quick) and everyone arrived back at glorious Darling Harbour at 7:45pm (15 minutes after schedule) while our original departure time with Sydney by Sail was at 5:30pm.

Maybe I might have added to the 15 minutes of extra time in beautiful Sydney Harbour due to my driving skills (laughs ahoy); oh well, who cares. This is an experience I will repeat as soon as possible, and if you love the water and/or Sydney Harbour and even Sydney as a city, then I highly recommend this experience for you; it is something that you will really cherish for the rest of your life. Thank you Sydney by Sail, and to one of my Sydney based clients for this awesome business related bonus.

Happy sailing.

Sydney Harbour late at night from a sailboat.

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Why? Awesome (twilight) sailing experience along Sydney Harbour, and you might end up driving the Yacht..
When: Different times and dates available. Twilight is from 5:30pm-7:30pm.
Where: Begins and ends at Darling Harbour (Festival Pontoon, Maritime Museum)
Cost: $100 plus per person depending on date and time of experience
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