After a sun-soaked 2026 that saw some of the best sailing events in years, we’re already looking ahead to 2027. From the legendary Round the Island Race to the friendly atmosphere of the Taittinger Regatta, there’s plenty to look forward to on the water and ashore. Whether you’re bringing colleagues together, entertaining clients or organising a day out with industry friends, these events offer something a little different. No sailing experience is needed, with our professional crews helping everyone find their feet, learn the ropes and get involved. For those who prefer to watch, a spectator yacht puts you close to the action, with time to relax and enjoy the company on board.
Legal Cup | 15th – 16th May 2027
The legal industry’s premier sailing regatta returns for its 36th edition, bringing firms together for two days of friendly competition on the Solent.
Starting from Hamble, teams will race before heading into Cowes for the Saturday night gala dinner. Sunday brings another chance to climb the leaderboard before the final prize giving. It’s a great opportunity to spend time with colleagues and meet others from across the legal sector, with plenty of stories to take back to the office.
Will your firm lift the trophy in 2027?
Round the Island Race | 10th July 2027
There are few sights in sailing quite like the start of the Round the Island Race. Hundreds of boats gather off Cowes before setting off on the famous 50-mile course around the Isle of Wight, with amateurs and professionals racing alongside one another. With a professional crew on board, your guests can play their part in a race that calls for teamwork from start to finish. Rounding the Needles and crossing the finish line together make this a memorable day, whether it’s your first race or an event you return to year after year.
Taittinger Regatta | 16th – 18th July 2027
Based at the Royal Solent Yacht Club in Yarmouth, the Taittinger Regatta combines close racing in the Western Solent with Champagne and a famously friendly atmosphere ashore.
Yarmouth makes a wonderful base for the weekend, with its harbour, pubs and restaurants all within easy reach. For teams or clients who would enjoy a sociable weekend with some competitive sailing, it’s a firm favourite.
North Sails Cowes Week | 31st July – 6th August 2027
After a brilliant 2026, with a new title sponsor, packed shoreside events and the return of the fireworks, there’s plenty of excitement building for Cowes Week 2027.
The appeal is the combination of competitive racing and everything happening ashore. Guests can get involved on board, follow the action from a spectator yacht and soak up that unmistakable Cowes atmosphere.
Join us for a day or make it a longer stay, with options to start and finish in Hamble, Southampton, Portsmouth or Cowes. We’ll help you build the day around your guests and what you’d like to achieve.
Dartmouth Regatta | 21st – 29th August 2027
With more than 200 years of history and racing against the beautiful backdrop of Start Bay, Dartmouth Regatta is a lovely way to round off the summer sailing season.
Ashore, live music, fireworks and a warm Devon welcome add to the occasion. For those looking to take their team or clients further afield, it offers a chance to combine time on the water with a stay in one of the UK’s most picturesque regatta towns.
Plan your time on the water
The best sailing events give people something to share. Learning a new role on board, working together around a racecourse and talking through the day over dinner all help relationships develop naturally.
At Britannia, we’ll help you choose the right event and build a package around your guests, plans and budget, taking care of the details so you can spend time with the people you’ve invited.
Speak to our team about joining the racing or watching from the water in 2027.
