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The annual Round the Island Race, which started back in 1930, is organised by the Island Sailing Club. It is a one-day yacht race around the Isle of Wight, situated off the south coast of England. The race regularly attracts over 1,400 boats and around 15,000 sailors, making it one of the largest yacht races in the world. It is also the fourth largest participation sporting event in the UK after the London Marathon and the Great North and South Runs. During the 2019 Round the Island Race, our boat Escapado finished first-in-class beating 9 other 40.7’s. In recent years the Round the Island Race has become a popular challenge for sailors at all levels of experience and abilities, attracting classic yachts such as the elegant J Class “Velsheda” as well as state-of-the-art, record-breaking greyhounds. Olympic gold medallists have tried their luck in the Sportsboat Rule and IRC classes, whilst grand old ladies of the sea, “Suhaili”, “Gipsy Moth IV” and “Lively Lady”, have given more modern designs a run for their money. The ISC Rating System division, for un-rated yachts, now exceeds the regular racers. For some of these sailors, this is their one race of the year and many use the event as a first taste of yacht racing. Entries come from all over the south and east coasts of England as well as from France, Belgium, Channel Islands and further afield. The event is reported in media across the world – from Brazil to Japan, Hungary to New Zealand. The race is a 50 nautical mile course round the Isle of Wight. Starting on the famous Royal Yacht Squadron line in Cowes, the fleet races westabout, to The Needles, round St Catherine’s Point and Bembridge Ledge buoy and back into the Solent to the finish line at Cowes. Whether you compete regularly or are new to the sport, taking part in the Island Sailing Club’s Round the Island Race is a day to remember, sailing in one of the world’s largest sailing events in some of the best sailing waters!
An absolute classic of a race. When in a 40ft racer cruiser, you're really mixing it up in the large fleet.
Day 1 Training Day Arrival on the boat and meet your skipper and crew, followed by a safety brief and the regatta programme. You will spend the day getting to know your crew, followed by provisioning, cleaning and organising the boat, getting her ready for the regatta, and training to bind the team into a race crew. We’ll have a crew dinner at a local restaurant. Because our boats are returning from the Caribbean just before this weekend, we will keep you updated via the crew group chat on the exact meeting time.
Off the iconic Royal Yacht Squaudron
Rounding an icon
Day 3 12th July 2026 Breakfast & Departure After the race day and celebrations on board, we invite you for breakfast aboard the boat before heading home. Before departure, we kindly ask everyone to help with a general cleaning and tidying of the boat.
Our Mission is simple: Provide fun, safe and rewarding sailing opportunities at an affordable price. Not everyone can afford a racing yacht or has friends or family that can. This should not be a barrier to entry. We keep costs low by involving everyone in the process and showing them the reality of what it takes to sail and race offshore. Our goal is to get as many people as possible to participate and leave having had the experience of a lifetime. We believe in putting safety first and allowing everyone to experience offshore racing in a supportive environment. We’d like to finish top of the leader board but the individuals on board will always come first.
They offer a range of small group and authentic sailing experiences, from Caribbean cruising to Ocean racing, at a budget to suit most.
Beginner
No sailing experience required. Perfect for newcomers.
Intermediate
Some sailing experience helpful. Comfortable on the water.
Advanced
Significant sailing experience required. Challenging conditions.
Active Crew Member
Full participation in all sailing activities.
Optional Involvement
Participate as much or as little as you like.
Passenger
Sit back and enjoy the ride.
Yes
Sharing the cooking & washing up
18
What to Expect Professional Instruction Our Skippers are experienced instructors that make every crew member feel welcome and tailor their delivery to the experience and style of the crew Competitive boat Although the taking part is often fun, we believe the full experience comes from pushing ourselves to the max and competing with other boats on the water with a view to win High safety standards Maintaining and equipping a yacht to a high standard is not an easy task. No expense is spared in ensuring the best equipment is selected and repairs are undertaken quickly and proficiently. No Passengers Although we are happy to provide sight seeing adventures, this experience is a regatta so you can expect to be actively involved in sailing the boat, there isn't any rail meat on our boats.
No optional extras
8-14°C
Variable conditions, longer days returning. Layers essential.
14-18°C
Improving conditions, good sailing with longer daylight.
18-24°C
Peak season with longest days. Variable winds, warmest waters.
12-18°C
Cooler temperatures, stronger winds. Experienced sailors.
6-10°C
Cold with challenging conditions. Limited sailing.
8-14°C
Variable conditions, longer days returning. Layers essential.
14-18°C
Improving conditions, good sailing with longer daylight.
18-24°C
Peak season with longest days. Variable winds, warmest waters.
12-18°C
Cooler temperatures, stronger winds. Experienced sailors.
6-10°C
Cold with challenging conditions. Limited sailing.
Tried and tested sailing experiences, from our pick of the world's best operators
All our trips are led by qualified skippers and sailing instructors
We only work with the most reputable sailing operators and yacht providers
Perfect for solo sailors looking to join a crew or groups wanting to charter
Our team is on-hand 24/7 to help you before, during and after your adventure
No dates available
Prices shown in USD are approximate conversions, using today's conversion rate. This trip is priced by the operator in GBP and payment will be taken in GBP.