Round the Island Race

Saturday July 1st

The Round the Island Race in association with Cloudy Bay is one of the most exciting and unique events on the annual sailing calendar, attracting around 1,700 yachts and 16,000 sailors, making it one of the largest multi-class regattas in the world. Competitors come from all over the UK and Europe to take part in the 50 nautical mile course.

Both amateurs and professional sailors take part in the Round the Island Race, giving everyone a taste of competitive racing at its best. Choose from a full boat package or join a yacht as crew for the experience of a lifetime on this truly unique event!

Please contact us for more details on 02392 222 221 or email [email protected]

Get all the latest news about the Round the Island Race website:

  • Suitable for amateurs & serious sailors
  • Our Sunsail Match First 40 Yachts have their own class
  • Full boat packages or individual places available

Your boat

Sunsail Events have the largest matched fleet of yachts in the world, ensuring that no-one has an unfair advantage in the Round the Island Race.

The only way to ensure you will win is to work as a team and use your sailing ability to get more out of your boat than your fellow competitors.

Sunsail Match First 40 - 3 Cabin Monohull Yacht

Drawn by Farr Yacht Design, the Sunsail Match First 40 by Beneteau is a thoroughbred cruiser/ racer, adaptable for both, to suit the sailors needs. The interior is modern, spacious and comfortable.


Be part of the action at the largest yacht race of its kind in the world. The Round the Island Race is perhaps the most coveted and certainly one of the largest multi-class regattas in the world and is the fourth largest participation sporting event in the UK. It has rapidly grown in popularity over the years amongst amateur and serious sailors alike. Sail with Sunsail in our identical fleet of Sunsail First Match 40s entered into their own exclusive racing class.

Charter includes:

  • Hire of a Sunsail Match First 40 from 1900 hrs on Thursday to 1700 hrs on Sunday
  • Overnight marina berths in Cowes Yacht Haven on Friday and Saturday evenings
  • Race entry fees into the Sunsail Match First 40 class
  • Shore based support from the Sunsail team for the duration of the event
  • Yacht coded and equipped to sail with 12 people
  • Yacht engine hours & wet weather gear

Price on enquiry

Hiring a Sunsail Skipper

Sunsail skippers can be hired for £240 per day including VAT and out of pocket expenses. The skipper will be resident on board your yacht for the duration of the event meaning that you will be limited to six crew members sleeping on board (yachts are coded and equipped to sail with a maximum of twelve people). 


Sunsail offers a full corporate branding service to attract attention and advertise your business at one of the largest regattas of the summer. There's lots of options, whether it’s hull logos, branded spinnaker or crew clothing to sharpen your team’s image. Plant your corporate identity in everyone’s mind by being big, bold and bright on the water.  

Choose Sunsail

Destinations worldwide

Flotilla routes

Types of yachts

40 yrs
Creating holidays

4 hr
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