We are fortunate in the Solent to have many sailing events take place each year.
Sailing events are suitable for both professional and amateur sailors. Offering many opportunities for those with no experience to get out onto the water and give sailing a try.
There are 2 types of regattas. Industry and open entry. Industry regattas are great for team building and networking within a specific industry, and open entry regattas are open to all to enter and race.
What can you do if you want to watch the sailing but don’t want to be onboard one of the yachts?
Bluetooth RIB Charter can help you get close to the sailing action. We have been hired as a skippered charter to transport friends, family, corporate guests and media teams around the Solent to spectate during the race or meet up with the racers during the event.
RIB’s can be rented from Bluetooth with a skipper to look after those onboard, or taken as a bareboat so that you can drive yourself.
We can get booked well in advance for some of the larger regattas and races, so please don’t leave it too late to enquire.
Solent Sailing Events 2027
Healthcare Services Regatta on 24th April 2027
The Healthcare Services Regatta has been established for over 20 years and is a sailing and networking event for companies and individuals from the healthcare, pharmaceuticals, healthcare tech and medtech and medical devices sectors.
Join up to 100 industry professionals join us for a weekend of competitive sailing, networking and socialising in Portsmouth, Cowes and on the Solent. Organised by Prometheus Sailing.
The Legal Cup. 15th – 16th May 2026
The Legal Cup is a regatta for members of the legal profession and their suppliers or clients.
Held over a weekend to not disrupt the working week, the sailing is open to all as qualified skippers are onboard the yachts. Qualified sailors can also enter the regatta with their own yachts. Organised by Britannia.
The Drinks Trade Regatta. 2027 date not yet confirmed.
The Drinks Trade Regatta is a sailing regatta for members of the hospitality trade. Brewing, wine and spirits companies compete on the water with on-trade retailers, restaurants and suppliers. Organised by Prometheus Sailing.
Cowes Classics Regatta. 2027 date not yet confirmed
Cowes Classics Regatta is about racing traditional yachts on the water and enjoying fabulous social events ashore. Metre boats, Classic Racing Dayboats and Yachts, Old Gaffers and Spirit of Tradition Yachts race varied central Solent courses. Cowes Classic Week regularly has over 200 boats entering. Organised by the Royal London Yacht Club.
Construction Industry ‘CRASH’ Sailing Cup. 2027 date not yet confirmed
The Construction Industry regatta is not only a great place for team building and networking. It’s also used to raise vital funds for CRASH.
CRASH is the construction industry’s charity that helps homelessness and hospice organisations with their construction projects – creating places that care for people when they are most vulnerable. Organised by Prometheus Sailing.
Financial Industry Charity Regatta on 11th June 2027
The Financial Industry Charity Regatta brings teams together from the insurance, finance, banking, accounting, legal and consulting sectors to compete in an industry sailing regatta. Whilst raising valuable funds for the Insurance Industry Charitable Foundation (IICF). Organised by Prometheus Sailing.
Sail to Reward Regatta on 14th June 2027
The Sail to Reward Regatta is for teams from the hotel and hospitality sector to compete in a sailing regatta. Offering a fun day for both sailors and non sailors, the day offers teambuilding, networking, whilst raising valuable funds for the Room to Reward Charity. Organised by Prometheus Sailing.
British Classic Week. 27th June-2nd July 2027
British Classic Week is a celebratory occasion for classic boat enthusiasts.
Enjoy good racing and spend time with others who share the appreciation of classic yachts.
It attracts entries from the UK, Europe and even further afield, from classic yachts built of wood, steel or aluminium to either a pre-1970 design or modern classic yachts built with the appearance of a classic. Organised by the British Classic Yacht Club.
Round The Island Race on Saturday 10th July 2026
Round the Island is a one-day yacht race around the Isle of Wight. The race regularly attracts over 1,200 boats and around 10,000 sailors. This makes it one of the largest yacht races in the world. Hosted and organised by Island Sailing Club.
If you’d like to join as an individual sailor, Promocean, Prometheus Sailing, and Britannia offer space on shared boats.
Admiral’s Cup. 13th – 28th July 2027
Admiral’s Cup starts in Cowes, Isle of Wight, UK and ends with the Fastnet Race which leaves Cowes on July 22nd 2027.
Racing consists of a combination of inshore and offshore racing.
The Admiral’s Cup was originally raced in 1957 and has been described as the “Holy Grail of Offshore Yacht Racing”. In 2025, it returned after a 22-year hiatus and was heavily contested by some of the most famous yacht clubs across the globe.
Organised by the Royal Ocean Racing Club.
SailGP Portsmouth – 24th and 25th July 2027
SailGP will be returning to Portsmouth in July. You can watch the professional sailors get up to record breaking speeds in adrenaline-fueled races. It really is a sight to be enjoyed.
Rolex Fastnet Race start – Saturday 24th July 2027
Join the racing sailors as they set off for the biannual Rolex Fastnet Race, which starts in Cowes and ends in Cherbourg.
Taittinger Royal Solent Yacht Club Regatta. 2027 date not yet announced
The Taittinger Regatta from Yarmouth, sponsored by Taittinger Champagne has a growing reputation as a great fun weekend of racing down in the scenic and very tidal Western Solent. Hosted by the Royal Solent Yacht Club.
Cowes Week, 31st July – 6th August 2026
Since 1826 Cowes Week has played a key part in the British sporting summer calendar and is one of the UK’s longest-running and most successful sporting events.
Staging up to 40 daily races for around 500 boats and is the largest sailing regatta of its kind in the world.
Renewable UK Industry Regatta – 2027 date not yet published
Join fellow professionals in the renewables industry to network, compete and build teams in the exciting environment of racing a sailing yacht. No experience necessary as yachts come with a professional crew to guide you. Organised by Prometheus Sailing.
Russell Cooke Silicon Cup, 2027 date not yet published.
Running since 2000, this regatta is open to members of the IT industry. Great for networking and raising funds for charity, this event has welcomed over 7,000 competitors on board and raised over £1 million. Organised by Prometheus Sailing.
Little Britain Challenge Cup 10th – 11th September 2027
The property and construction industry’s regatta brings together thousands of people from the industry to sail, socialise and fund-raise.
Little Britain attracts project teams celebrating success and companies looking to team-build and entertain key clients.
You can book to sail in the Little Britain Challenge Cup with Prometheus Sailing and Britannia.
Contact the team at Bluetooth RIB Charter to rent a bareboat or skippered RIB to enjoy Sailing Events happening on the Solent.