Round the Island Race Fundraising Challenge 2026

Looking for a fun but competitive team sailing challenge?

Sign up to our 2026 Round the Island Fundraising Challenge – Friday 13 – Sunday 15 March!

We’re inviting crews to compete on board our iconic 72ft Challenger yachts.

The challenge:

Be the first to sail round the Isle of Wight and raise the most money for Tall Ships Youth Trust’s vital youth development work.
Smash the current winning time of circumnavigating the island in just under 6.5hrs, reaching speeds of up to 10.5 knots.

Do you think your team has what it takes to beat the wining crew from Met Police Sailing Club? If so, read the sections below to find out more on the challenge, itinerary, costs and fundraising.

Or, book your place today by contacting Hannah Langley:

hannah.langley@tallships.org or call Hannah on 02392 832055

The Weekend

The aim of the challenge is to circumnavigate the Island leaving the Needles, Ventnor, St Catherine’s lighthouse, Bembridge and the rest of the Isle of Wight to port, finishing near Cowes in the fastest time possible.

Start date: Friday 13 March 2026 End date: Sunday 15 March 2026

Itinerary: Board your yacht in Gunwharf Quays at 1000 Friday for a day of sailing practice in the Solent. Hone your skills and keep an eye on the competition before arriving in Cowes. Crew will be provided with lunch and dinner on board.

Saturday morning brings race day, with an early ‘Le Mans’ style start. The aim will be to circumnavigate the Isle of Wight leaving the Needles, St Catherine’s lighthouse, Bembridge and the rest of the Island to port before finishing near Cowes hopefully between 1630 and 1800.

Enjoy a two course prize-giving dinner and raffle at the Island Sailing Club in Cowes on Saturday night.

Sunday brings a more relaxed start to the day with the plan to motor .back to Gunwharf Quays for departure between 1100 and 1200.

Please note, this itinerary is subject to the weather and while the intention is to race round the Isle of Wight on the Saturday, the Skipper(s) will review the route and take into account weather conditions and other factors.

The Costs

The full weekend based on teams of 12 is £3,900 per boat or £325 per person

This includes:

Three days sailing on board a 72ft Challenger yacht
Professional TSYT sailing staff; Skipper and First Mate, who will support your team throughout the weekend
All food and refreshments on board
Saturday evening two course dinner at the Island Sailing Club, Cowes
Full sailing and wet weather safety gear
Berthing
Insurance

We ask for a 20% deposit at the time of booking, with the final balance payable 8 weeks before the event, thank you.

The Fundraising Challenge

While this price covers the event costs, it does not include a charitable donation. We therefore kindly ask all teams to commit to raising as much sponsorship as possible as part of the weekend, and suggest a minimum target of £3,000 per boat (£250 per person).

We are passionate about ensuring all young people have access to our life-changing experiences at sea. Every penny you raise will go directly towards helping more young people living with disadvantage take part in a life-changing TSYT voyage.

Here is the impact you can make:

“I struggled with socialising and communicating as I have a slight processing delay as part of my autism. This resulted in me becoming anxious in unfamiliar environments and badly impacted my confidence and self-esteem. I had never been away from home without my parents…now I was embarking on a voyage with a group of strangers, sailing to unfamiliar places. I did feel very anxious, but I was determined not to miss this opportunity”

Alex, 18 – who wouldn’t have been able to sail with us, without financial support.

Our fundraising team can offer advice and guidance along the way, and you’ll be given all the tools you need to kick-start your fundraising activities.