Pack your island holiday with fun things to do
The Isle of Wight is one of the UK's most exciting destinations for festivals and events! There's a wide variety of year-round activities and events, including one of the UK's biggest and best known music festivals, the world's oldest sailing regatta, and a food festival dedicated to one of our most famous exports, garlic!
Jack Up Events presents Dancing Queens & Boyband Dreams
Retro Staycations, the Isle of Wight’s award-winning glamping retreat and vintage campsite, is set to host a spectacular summer weekender packed with music, nostalgia, and festival vibes.
Proms '26
Have your flags at the ready and don’t miss your chance to be part of this special occasion!
Round the Island Race
The iconic Round the Island Race is one of the largest of its kind in the world. Regularly attracting over 1,200 boats and around 10,000 sailors, it’s one of the UK’s biggest sports participation events.
The 2026 Special Evening of Opera
Enjoy a special evening at the opera in support of Polly’s Fund, led by professional Italian singer and conductor Andrea Colombini as he presents “An Evening at the Opera" in Cowes and Yarmouth.
Wytwoods Festival
Bringing you multiple bespoke stages and a curated dance music lineup including Max Dean, Prospa, Sidney Charles, Alisha, Dr Banana, Jamback, Wheats - plus 50+ additional artists. They will also be hosting two days of wellness and arts classes and takeovers.
Ventnor Fringe
Discover the best new music, comedy and theatre at the Isle of Wight's largest arts festival, Ventnor Fringe. Taking place over 10 days the festival transforms the Island's southernmost town and surrounding coastline to become a stage for hundreds of performances, with venues in even the most unlikely locations.
Festival of Heroes
Festival of Heroes returns to Brading Roman Vill this July with all your favourite characters who can't wait to meet you!
IW Pride
Isle of Wight Pride returns to Ryde on Saturday 18th July for another day of celebration including the annual Pride Parade, Pride Community Village and a line-up of fabulous entertainment at The Pavilion Bar.
Sail GP
The most exciting racing on water is back in Portsmouth this summer. The Emirates Great Britain Sail Grand Prix | Portsmouth sees 13 national teams battling it out in identical high-tech, high-speed 50-foot foiling catamarans.