The  Round the Island Race is an annual event where you sail around the Isle of Wight. It is one of the biggest yacht races around and attracts competitors from Europe, the USA and all over the UK. Starting and finishing in Cowes, Isle of Wight you will race West around the Island passing famous landmarks such as the Needles and St. Catherine’s Point.

Whether you are new to racing or a seasoned crew member, the Round the Island race ticks all the boxes. Racing alongside over a thousand other yachts is an exhilarating experience and makes for many stories.

Jolly Parrot sailing are offering the complete package. You will start this exciting weekend joining the yacht in Hamble.  After safety briefs have taken place you will head out for a day of training, coaching and bonding with your fellow crew in the Solent.

Saturday begins with a prompt start ready for a busy day of racing. You will get the opportunity to be an active member of a functioning race crew on board one our fleet of yachts. Following our exciting day of racing you will head into Cowes, the mecca for UK Yacht racing where there is fantastic“après-sail” entertainment laid on to celebrate the day.

On Sunday you will prepare the boat and take a leisurely cruise from Cowes back to Hamble.


2026 Round the Island Program:

Race Training

Friday 10th July 2026

Race Day 

Saturday 11th July 2026

Cruise Back

Sunday 12th July 2026

Whats Included?

  • Professional Skipper
  • Training
  • Team Jolly shirts
  • Accommodation on board (maybe shared)
  • Breakfast, lunch and snacks 
  • Race entry
  • Safety kit
  • Fun!

What's not included?

  • Personal insurance
  • Expenses ashore

How to book

It's easy! Scroll down and click on book, confirm that this is the event you want and then complete your details on our secure online booking system. A 25% deposit is all that's needed, with the balance payable 45 days before your event starts.

SELECT YOUR COURSE

Book online now

Event Price:

£950


Own cabin option:

£1250

RYA Training Center

See what our clients say

  • Great week with Jolly Parrot our instructors Ian and Lissie were excellent and prepared us above and beyond for our Yachtmaster assessment at the end of the week. Would definitely recommend for any of your training.


    Ben
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  • Amazing 10 days with my instructor Ian working on my yacht master coastal prep course, which I successfully passed the day after the course. Great company couldn’t recommend them enough booking was easy and very well informed thanks to Rachel working behind the scenes.


    Greg
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  • Absolutely incredible! Recently, I completed Jolly Parrot’s ‘Novice to Day Skipper’ course, and it was one of the best experiences of my life! Not only did I learn to sail, but the course also improved my confidence massively. The instructors were all so lovely and incredibly knowledgeable. Greg was my instructor for the Day Skipper portion and I couldn’t imagine anyone better suited for the job - An excellent instructor with impeccable humour. I met some amazing people during this course (namely my crew mates Bene, Doug and Flo), and overall had a wonderful time :)


    Georgia
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  • Novice to Day Skipper course with Alex & Jason I was eager to learn to sail and at the same time to have relaxing time (holiday-like). It worked well for me, the instructors were cool and I was lucky to meet good colleagues sailors and have good time on the way. Keep rocking Jolly.


    Nikola
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  • 16-week Fast-Track I completed the 16-week Fast-Track program with Jolly Parrot, starting as a complete beginner with no prior sailing experience. From the moment I stepped aboard, the instructors—Ian, Greg, Rob, and Jason—became my guides, transforming my raw inexperience into something far more seasoned and confident. With their patience, skill, and unshakable belief in every student, they taught me far more than I could have imagined. If you’re considering joining, I can wholeheartedly recommend Jolly Parrot. The program is well-structured, and the instructors are highly knowledgeable, making it an excellent choice for anyone looking to develop their sailing skills.


    Tobias
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  • We spent a wonderful 11 days in November 2021 with Jolly Parrot. I completed the Coastal Skipper Combined course and my wife the Comp Crew. Instructors Flipper, IanG, Hailey, and Tom were all exceptional in their own unique way and we came away with more rounded skills and knowledge as a result of their patient teaching methods. Clive and Rachel did a fabulous job of shuffling schedules and boats to accommodate our different experience levels. Expect to be challenged on the Coastal Skipper course! We made some abiding memories, some long-term connections and friends, and hope to return soon for the next challenge maybe a mile-builder.


    James
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