Round the Island Race
Saturday 10 July 2027
We’re off Cowes, counting down to the start. Boats are crossing in front of us, the tide’s running and we’re looking for a gap. Get across the line with room to sail and we can get Bossy Boots moving west towards the Needles.
Join me, Matthew North, aboard my Contessa 32 for one lap of the Isle of Wight. You’ll take your turn at the helm, trim the sails and help decide where we put the boat. First-time sailors are welcome.
£1,200 per person plus VAT when you book by 31 December 2026.
Standard price £1,440 per person plus VAT.
The race weekend
Before the start
We’ll get to know the boat and each other, go through the safety briefing and look at the weather, tide and course. We’ll agree who does what on the start line and talk through the manoeuvres we’re likely to need.
Saturday 10 July · Race day
We’ll start off Cowes and race west through the Solent to the Needles. From there it’s along the south coast past St Catherine’s Point, round Bembridge Ledge and back into the Solent for the finish off Cowes. Each leg asks something different of the crew. At the start it’s about finding space and clear air. Later it might be about spotting a change in the breeze or working out where the tide will help us.
After the finish
We’ll talk through the race together. Where did we gain ground? What would we do differently? And how did it feel to sail a full lap of the island in a fleet that size?
Expect an early start and a full day afloat. I’ll confirm the joining marina, meeting time and plans around race day before you book.
Your role aboard
I’ll show you the jobs and coach you as we go. We’ll swap roles when the race allows, so you can feel what a change in trim does at the tiller and see what the crew needs from you when it’s time to tack or gybe.
Helm. Take the tiller and get a feel for how Bossy Boots responds as the wind and sea change.
Sails. Trim the main and headsails and work together through tacks, gybes and sail changes.
Tactics. Watch the fleet, read the tide and help decide where we can find a better line.
The boat
Bossy Boots — Contessa 32
A small boat with a serious reputation.
The Contessa 32 is one of Britain’s best-known offshore designs: balanced, responsive and immensely rewarding to sail well.
Bossy Boots has been extensively upgraded, including a new mast, new rudder, modern electronics and a competitive sail wardrobe.
She will not disguise poor sailing behind unlimited speed.
Every clean tack matters.
Every good start matters.
Every small gain is earned.
That makes her an exceptional boat on which to learn how to race properly.
What’s included
A crew place aboard Bossy Boots for the Round the Island Race
Skipper, pre-race briefing and hands-on race coaching
Food and drinks aboard on race day
Lifejacket, onboard safety equipment and loan waterproofs
Bring warm layers, deck shoes or sailing boots, sun protection and a small soft bag. Let me know in advance if you’d like to borrow waterproofs.
Frequently asked questions
Can I join on my own?
Yes. Places are booked individually. We’ll get to know each other and work out our roles before the start.
What if I’ve never sailed before?
You’re welcome. I’ll talk you through your role and help you get involved from the first manoeuvre. Expect a full, active day on the water.
What if the weather changes?
The Island Sailing Club sets the race arrangements and may change them if conditions require it. I’ll keep you informed about what any change means for the day and your booking.
Join the crew
Tell me a little about yourself and any sailing you’ve done. I’ll confirm availability and talk you through the weekend.