Round the Island Race 2021

by | Jul 20, 2021 | Racing, Round the Island Race

In July 2021, 2 years after the the last Round the Island Race, over 1000 boats all set off in the annual spectacle that is the Round the Island Race.

Challenger 1 took part as part of there Rolex Fastnet training.  Here’s how it went –

An early start to the Round the Island Race!

Well, no-one told me when I signed up for this that I would have to get up just after I had gone to sleep and be on the boat by 3:30am! Yet when we all started arriving there was a buzz of excitement. Today was the Round the Island race, and today we were going to put into practice all of the skills and teamwork that we had built over the last race and training weekend. This time we were competing, and this time we were going to be the first Challenger across the line.

We slipped lines and headed out from Portsmouth in the dark to the start.  Our start time was 06.30 so we motored over towards Cowes enjoying bacon and sausage sandwiches, the first of many, were prepared and consumed on the way. It was quiet on the way out of Portsmouth, and then as we neared Cowes, we saw them. Hundreds and hundreds of boats, and more coming. Suddenly we were surrounded, and on the lookout, Adam with the roving fender ready to protect the boat to the next potential bump point as fast as he could.  Luckily, and somewhat surprisingly, there were no incidents. The ten minute race countdown began, the five minute, the one minute, the anticipation was rising in the team even if there was very little wind, the ten second countdown and then the gun. We were off.

Round the Island Race 2021 start line

 

No wind. Light airs was possibly an overstatement but the 2kts of tide, which really was the only element carrying the boats over the line started us off on our adventure.  This was going to be a long day!  Slowly the wind started to fill in after an hour or so, filling in to a stronger and stronger steady breeze as we sailed up the Solent towards Hurst castle the Solent narrowing on our way to the Needles. The racing was exhilarating as we approached this narrowing channel with increasing numbers of yachts surrounding us each tacking in quick succession within meters of each other. The Team focussed really hard, trying their best to be as quick, slick and as efficient as possible with each tack, we really had the bit between our teeth totally focussing on our own individual tasks as well as those of others, ready to help each other as necessary and helping to keep a lookout and assist our Skipper Mike as much as we could. It started to rain as our Challenger heeled over hard but no one really minded we were having real fun. Our Skipper, Mike, First Mate Mike and Watch Leaders Mark and Rob (Bex was stuck in Jersey) kept us moving fast and focussing. Everyone working really hard and now everything was going like clockwork.  Captain Mike was impressed, we could tell.

The Needles

The Needles

 

By the time we got to the Needles the breeze was really picking up, and we rounded this iconic beautiful landmark on a port tack at a safe distance. All the other yachts were moving faster now and we could see many boats behind and in front. 35 miles to go, the other Challengers behind us.

Some of the other yachts put their spinnakers up as soon as they rounded the Needles, but we reached across to St Catherine’s point with the Yankee and Staysail full making good way.  Time for another bacon sandwich and the biscuits came out, we are a hungry lot.  Just before we reached St Catherine’s point we saw the perils of taking a risk in the inshore passage towards the shore, a yacht had ran aground close to the shore and was now surrounded by a supportive gamut of onlookers in ribs, awaiting a tow from the RNLI.

Sailing round the back of the Isle of Wight

Sailing round the back of the Isle of Wight

 

As we rounded St Catherine’s point it was time for us to put up our spinnaker for our downwind run. A Clipper yacht was gaining ground on us so Skipper decided it was time to raise the spinnaker. The team having never done this before were taken through each step by Mike, Mike, Mark and Rob. The instructions were excellently clear as we raised the spinnaker pole and then the huge blue and yellow striped Kite. It was wonderful to see the kite fill as the wind took hold. We were all excited and as we took a look behind us, in front of us and close by we could see miles of colourful beautiful Spinnakers being flown from the myriad of yachts in the race. It really is a staggering sight.

Spinnaker

Spinnaker

After a few miles we reached Bembridge on the east corner of the Isle of Wight. With the wind steady and rather than performing a complex gybe manoeuvre with the spinnaker we watched in awe as Rob one of our watch leaders made his way climbing along the sheet to the end of the pole to spike it to allow the spinnaker to be free and in a smooth operation we all grabbed at the spinnaker and pushed it down into the companionway towards Austin in the cabin below. We watched a Clipper boat close by try to gybe which didn’t go altogether very well as it flew uncontrollably amidst the loud shouts of the crew. We were glad that wasn’t us as we pulled away from them at Bembridge towards the forts.  Rounding the mark within the calamity of other keen racers we reached onwards passing close by a huge blue super yacht with a large sailing yacht and large motor boat placed on board (this seemed a bit excessive to us but hey billionaires can do what they like) we hardened up and sailed in the steady breeze towards the forts and then onwards towards Cowes and the finish line.

The finish line up ahead

The finish line up ahead

Now, even more so, we felt like we were in a race. Coming along the outside of the pack that had taken the inner path between the fort and the island, we had a strong breeze and despite the tide being against us were making around 8knts under full sail.  It was touch and go as to whether we would need to tack in order to get a line to the finish, and with Guy at the helm we pinched in as close as we could, maintaining the best course to windward and keeping the power on.  We were passing smaller boats, and leaving behind our competition, the other Challengers and Clippers, clearly the outside track was a good strategic move and our sailing was top notch. We were all very happy and keen to do better and better.

 

After great sailing by Guy, Dean then took the helm clearly becoming ‘Man of the Match’ (ps England vs Ukraine 4-0 – what more can we say!) to power us towards the finish line, Skipper Mike keeping us on our toes with numerous tweaks to the sails as we grasped every opportunity to reach the next yacht and the next, many we passed as the little blue ferry of the Race committee came into view, it was clear we were in a good line to make it. Our Challenger heeling hard the breeze filling the sails we all gave a loud cheer as we crossed 174th out of 1168 boats in 8hrs 12 mins (appreciating that starts were staggered) we were all super happy, an excellent time, a fantastic sail and terrifically great fun. We had all done really well and Skipper Mike was chuffed to bits.

 

For details of future Round the Island races and how you can take part have a look here:  www.firstclasssailing.com/round-the-island-race-2021

The race is organised by the Island Sailing Club.

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Maurice MacSweeney profile pictureMaurice MacSweeney
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Hi Maurice, we're so pleased to have been with you from the start of your sailing journey. That's great that you enjoyed the ratio of students to instructor and felt confident with the levels you achieved. Thanks for the review, we hope you manage to get plenty of sailing in after all the hard work you've put in.
Marty Stromquist profile pictureMarty Stromquist
15:22 24 Oct 25
I just finished another training week at First Class Sailing’s training center. The week was dedicated to Yachtmaster Ocean Theory, with a highlight on Celestial Navigation. The instructor, Nigel Rennie FRIN (Fellow of the Royal Institute of Navigation), was fantastic. It was very fast-paced, but covered the basics and theory behind Celestial Navigation. The jewel of the week was Rennie. His abundant patience, coupled with his experiences and passion for the art, made the week incredible. First Class Sailing have the best instructors. They know their craft and have real-life experience to make training both fun and memorable. Well Done!
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Thanks Marty. We're so pleased you enjoyed Nigel's expert guidance and passion for sailing. Like all our instructors, he loves teaching and sharing his knowledge, but manages to make it fun too. Thanks for the recommendation.
Anne-Laure McLeman profile pictureAnne-Laure McLeman
10:07 15 Oct 25
Being in an all female boat is a great way to learn. Kirsten, our instructor, had a very calm and reassuring style. The small size of the group (only 3 of us) meant we got a lot of attention and many opportunities to practice. Such a good week!
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Thank-you for the review Anne-Laure. That's great that the all female option suited you well and you enjoyed learning with Kirsten. Hopefully all that practice has set you up well for future sailing. Good luck!
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Really great experience with First Class. My partner and I did our Day Skipper over two weekends with our instructor Mark. He was fantastic. Patient as we learned and made the whole thing fun. The boats are great and organization by First Class was seamless. Would totally recommend.
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Thanks Angus. That's good that you enjoyed Mark's style of teaching and also had lots of fun along the way. Wishing you lots of happy sailing in the future.
Tricia Bunten profile pictureTricia Bunten
18:48 07 Oct 25
I just finished a fantastic week taking my Day Skipper practical with First Class Sailing and I highly recommend them. I chose the Women Only week and had an incredibly patient instructor who was able to help each of us individually with areas of weakness but also worked great with us as a group. I had never sailed in the Solent before and it was the perfect location for this class. I am so grateful for First Class and my instructor for helping me build confidence and experience.
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Response from the owner 16:59 04 Nov 25
Thanks Tricia, we're so pleased you enjoyed the Women Only week and had a positive experience. We always say that the Solent really is one of the best places to learn and it has some beautiful scenery to explore too, so that's good that you appreciated it. Hope you manage to get out on the water soon.
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They do say that what sets great companies apart is customer service. This is my third time with first class sailing the first time was a few years ago when we did our competent crew it was one of the best weeks of our lives. Then we came again in August for the kids to do their competent crew and my wife and I to do our day skipper course. Unfortunately when I did my day skipper course the weather was terrible and I was unable to have a good session to pass. So Jake said to me you can come back and have a free weekend on us to enable you to pass. And again I had a fabulous weekend. There was just three of us on the boat. A wonderful instructor, Tom, and another student. Tom was an excellent instructor he was relaxed, he had great experiences, he got on with the practical part of sailing not just a lot of theory and he was thorough. He had lots of practical tips to make sailing easier and had some good exercises forest to try. We had a super trip down to Yarmouth where he cooked a wonderful dinner and then we went to the pub. Where we met another first class sailing group and spent the evening listening to their tall tales. The following day we had a super sail back to Southampton, with lots of cool exercises and I was thrilled to pass my day skipper.
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Response from the owner 16:46 04 Nov 25
Thanks for the review Evan and congratulations on passing your Day Skipper practical, the hard work has paid off. That's good that the whole family joined you for one of the trips and so now hopefully you have some willing crew members for future sails. Good luck!
hugo kirby profile picturehugo kirby
15:26 09 Sep 25
great course with a very engaged and helpful instructor - who was happy to go outside the curriculum and give us the benefit of his wider knowledge - throroughly recommended
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That's good that you appreciated the experiences and extra knowledge that the instructor passed on. Thanks for the recommendation.
Justin Brooks profile pictureJustin Brooks
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We would highly recommend First Class Sailing.

Very well organised with a top quality instructor who provided tuition tailored to our differing needs.

A fantastic option for a couple wanting an entire boat to do a mixed Competent Crew / Day Skipper itinerary.
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Thanks Justin. We always find that mixing the Competent Crew & Day Skipper works well, so that's great that it worked for you too. Hope you manage to get out on the water soon and put all your learning into practice.
ChrisC profile pictureChrisC
15:37 22 Aug 25
Great experience doing a Yachtmaster Offshore prep week followed by exam. Lots of useful paperwork up-front for the course admin and training exercises. The 3-day prep format worked well and Hayley did a brilliant job of cramming in the training over those days. Lovely modern boat too called Sazerac. Will be back.
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Hi Chris, thanks for the review. Congratulations on gaining your YMO qualification. There's a lot to cover, but as you've found, the hard work really pays off. We look forward to welcoming you back in the future.
Miles Barr profile pictureMiles Barr
11:27 03 Aug 25
I completed my Competent Crew and Day Skipper Practical with First Class Sailing. It was a great experience. I hired the whole boat each time, taking my family members along who also earned their Competent Crew qualifications.
Response from the owner 15:21 21 Aug 25
Thanks Miles. That's great that hiring the whole boat for your courses worked well for you all. Now that your family have their comp crew qualifications, you'll have plenty of help onboard for future sails! Good luck.

star rating  Yachmaster Ocean Theory  - I just finished another training week at First Class Sailing’s training center. The week was dedicated to Yachtmaster Ocean Theory, with a highlight on Celestial Navigation. The instructor, Nigel Rennie... read more

avatar thumb Marty S
October 24, 2025

star rating  All female boat for day skipper practical  - Being in an all female boat is a great way to learn. Kirsten, our instructor, had a very calm and reassuring style. The small size of the group (only 3... read more

ALMC62
October 15, 2025

star rating  A consistently great experience  - Over the last few years First Class Sailing have taken me all the way from complete novice to Coastal Skipper, with theory and other courses along the way (like VHF,... read more

avatar thumb Mo M
October 30, 2025

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