First Offshore Race For Bossy Boots

First Offshore Race

It’s mid-afternoon. We’ve just exited the Solent on our way to Deauville in France… and stopped.

Worse than stopped actually. Bossy Boots wants to spin slowly in circles while the rest of the fleet somehow sail away from us into the distance.

There is absolutely no wind.

This isn’t cruising. We can’t just start the engine for a bit. This is racing. That means patience, persistence and trying not to lose motivation while drifting sideways in one of the busiest shipping areas in the world.

At this point we are genuinely considering giving up and heading home before darkness falls.

But back to the beginning.

At 7am that morning we slipped lines in Hythe and headed for the start of the JOG Race to Deauville. It was the first race ever for Bossy Boots since becoming a race boat at all, following her huge refit over the winter.

I’d entered double-handed with a good friend, Will. After missing the first race of the season due to strong winds, we were excited just to finally get going.

The 9am start went reasonably well. We crossed slightly late on starboard tack, but then immediately lost ground when the genoa sheet snagged itself around the bow fitting. Something it had never done before… and hasn’t done since.

Typical racing.

Suddenly we were right at the back of the fleet.

Still, there was only one direction to go now.

The first few hours were brilliant sailing. A steady 10–15 knots pushed us east past Portsmouth and out beyond the forts. Full sails up, boat moving nicely, and despite being towards the back we were still in touch with the fleet.

Then everything changed.

A large cargo ship passed nearby throwing a heavy wake across the water. At exactly the same moment the wind disappeared.

Completely.

Bossy Boots is a heavy old boat by modern racing standards, and with only a few knots of breeze she simply stopped moving.

We tacked.

We gybed.

We adjusted sails endlessly.

Nothing worked.

Hour after hour drifted by while the rest of the fleet somehow escaped ahead. Maybe they found pressure. Maybe they were just better sailors.

Probably both.

Eventually, after nearly three hours of frustration, I decided to try one final port tack before admitting defeat and turning for home.

Slowly… the boat started moving.

One knot.

Then one and a half.

Then two.

Then suddenly three knots.

We’d escaped the wind hole.

Barely.

We still didn’t have much hope though. The forecast showed light winds all night, followed by another calm the next morning. Our goal had never been to win the race. We just wanted to make it to Deauville in time for a beer the following afternoon.

At that point even that seemed ambitious.

Still, we carried on.

Sails trimmed. Autopilot on. South across the English Channel we went.

Just the busiest shipping lane in the world.

No pressure.

The little Contessa settled into her rhythm beautifully, sailing under full main and No.1 genoa from  Sanders Sails at around 4–5 knots in 6-8 knots of apparent wind.

As darkness fell we moved into our three-hour watch system. It became properly cold overnight. The sort of damp offshore cold that slowly creeps through every layer no matter what you wear.

Tea and biscuits became essential survival equipment.

By now we couldn’t see another yacht anywhere. We were convinced we were near the back of the fleet.

But the beer was maybe… still possible.

As dawn arrived and the warmth slowly returned, our phones began buzzing with tracker updates as we closed on the French coast.

Then we noticed something strange.

The fleet ahead had stopped.

Completely stopped.

Every boat clustered near the finish line but barely moving.

At first we thought they must have already finished and anchored. But no — they were trapped in another huge wind hole right on the finish.

Some boats even dropped anchor temporarily to stop the tide sweeping them backwards away from the line.

But behind them, we still had breeze.

Even better, the forecast now showed an afternoon sea breeze building.

Suddenly everything changed.

Not only were we going to make the beer… we might actually catch people.

The wind shifted aft, the sea flattened slightly, and up went the spinnaker.

Now we were racing.

Sail trim became obsessive. More tea was consumed. Bossy Boots surged south towards the line chasing boats that had been hours ahead only that morning.

Eventually, after more than 30 hours of light winds, cold nights and relentless concentration, we crossed the finish line off Deauville.

Exhausted.

Very ready for a beer.

Then we checked the results.

Second place in the double-handed class.

And 14th overall out of around 40 boats — most of them larger, newer and fully crewed.

What an incredible debut for Bossy Boots.

The shorts finally went on, we headed ashore into beautiful Deauville, and enjoyed one of the best beers I can remember.

New friends made.

A proper offshore race completed.

And proof that sometimes patience matters far more than speed.