Day 3,512 - Double Bay, Australia 22:15hrs - January 10 2017 Gangsta Sailors

"They're the real gangstas!"

Ignoring the power yacht with decks awash with attention-seeking Kardashian lookalikes and Kayne West wannabes bouncing to a bass that shook the dock, the professional photographer, who had flown over from France to film the race for a sailing documentary, and along with most of the crowd at Double Bay, was focused entirely on the skippers and crews gearing-up and launching their colorful fleet of sleek 18 Footers.

With an invitation from cruising buddy Chris Nicholson to watch the first race of the WC Trappy Duncan Trophy, and even sail on one of Sydney's historic 18 Footer sailing skiffs, Catherine and I arrived in Double Bay just in time to watch the lads rig-up, then clamber on the spectator ferry to witness the fastest class of skiffs in the world - Formula One racing with sails.

The 18 Footers, modern descendants from an over 100-year old Sydney sailing tradition, resemble the old heavy wooden skiffs from yesteryear in length only. The original skiffs, that still sail today in a slower but more regal league, accommodate crews of eight with at least one dedicated bailer to keep the boat afloat. But these carbon fiber rocket ships, sailed by crews of just three, weigh a mere 375 lbs, carry more than 100 square meters of sail, and seem to fly more than float, regularly reaching whiplash speeds of over forty knots.

Nico, as he's know in the sailing world, has represented Australia twice in Olympic sailing, is a Volvo Yacht Race skipper and has won six world championships, and along with his A-team crew, Ricky Bridge and Mike McKensey, were first to cross the finish line in Smeg, a favorite in the race with 3 to 1 odds and who secured their gangsta reputation by streaking red across a busy Sydney Harbour at speeds that put even the Manly Fastcat Ferries to shame.

After the race an official RIB raced over to the spectator ferry to transfer me to Smeg, to join them on a sort of victory lap around the harbour. Nico had briefed me ashore on a few of the more noteworthy safety tips - how to quickly tear off my harness should I become trapped under the boat, where to locate the knife to cut myself, or another, free from entangled rigging, and instructions on how to use a tiny oxygen bottle so if Plan A and B both failed miserably, would provide a few seconds of air to arrange a Plan C, or to just panic. This was not going to be the relaxing Sunday afternoon sail I imagined, and really, the word 'skiff' is an entirely misleading and inadequate description of these boats.

After bundling from a moving RIB onto Smeg, which of course with no motor was underway, Nico, Bridgy and Mike quickly strapped me into a harness and without fanfare or banter instructed me to slide my ass over the edge of the wing, throw my weight onto the harness line and stand up! Sandwiched between a Bridgy and Mike, the three of us provided the counter weight as Nico worked the tiller. We raced east up the harbour in 20-25 knots of wind, and it was magnificent - I was racing on an 18 Footer in Sydney Harbour with the best sailors in the world! And in between losing my balance and swinging wildly out of control, I like to think, perhaps at least for a few seconds, a casual and distant observer may have mistaken me for one of these sailing elites - but then we raised the spinnaker, and we capsized, twice.

For the record, and to protect the reputation of these seafaring superstars, Smeg did not capsize once during the race. Other 18 Footers sure did, indeed, one almost T-boned a Manly ferry before somehow somersaulting upside down. But Smeg, with her accomplished crew of three, stayed above the waterline. However, with the spinnaker up in 25 knots of wind, and 200 additional pounds of slow-moving obstructive weight onboard, things got a little ugly.

We did have a few good runs with the spinnaker up, but after the second capsize and not wanted to risk inflicting irreparable damage to skiff or further injury to her crew, it was universally agreed that perhaps it would be best for all concerned if I returned to the club in the RIB.

Later that evening in the yacht club, after swapping stories and sharing a few celebratory jugs of beer, I must admit I was feeling a little guilty about the fresh wounds my fellow dory mates had sustained due to our capsizes, so it came with a certain degree of relief when I noticed that almost the entire fleet of racers were nursing fresh cuts, scrapes and puncture wounds from the afternoon's race. I had my own trophy wounds, proof of my time, however brief, sailing with the elite gangstas of Double Bay.

Thanks guys! And next time I promise to remain on the spectator ferry.