Cycling around the Isle of Wight 

When my sister first started cycling, several years ago now and a year or so before I owned my first road bike, my mum took her on one of her first cycles around the Isle of Wight – 100km. A pretty long way for a beginner cyclist just learning to use clips and one thing Jilli was great at at that point was falling off. She crashed or had one of those slow, awkward sideways dismount falls repeatedly throughout the day. And yet there must have been something good about it – or my mum is very persuasive – because it wasn’t long until she was doing it again. My mum loves the cycle so much she’s done it 5 or 6 times. On the other hand …. I had not once made it over to the Isle of Wight with my bike.

The Isle of Wight is an island of the south coast of the UK, just off the coast of Portsmouth. I knew it growing up because of the annual Cowes Week – a huge sailing regatta out of one of the towns in the island. But it’s also really popular for cycling and has become more so since the establishment of the Isle of Wight Randonnée – a free 100km cycling all around the island over the May bank holiday.  There is now an official “route” for cycling round the island which is well signposted in both directions.

And so the plan was to cycle around the Isle of Wight over my mum’s birthday weekend. Mum invited down my aunt and uncle, their three daughters, and the two boyfriends. Then my sister, Jilli, decided she would fly home from Mallorca where she works for the weekend as a birthday surprise for mum. So we ended up with ten of us for the long weekend!

The alarms were set for 6.30am on Sunday morning and so we were a slightly subdued family as we loaded our bikes into four cars under a light, grey drizzle, all slightly surprised by the lack of clear blue skies. Mum was quite stressed by the idea that we might miss the ferry – we were aiming for the 8am ferry across from Portsmouth but at that time in the morning there was only one an hour so it was important to make it! We had a lot of bike wheels to put on once we reached the carpark and we sent Jilli off to buy tickets for everybody. Really there was no need to worry, every single one of us managed to roll up to the ferry in plenty of time.

Bikes secure, we went indoors for tea, coffee, porridge and bacon sandwiches from the cafe while the ferry chugged through the drizzle to Fishbourne. We rolled off and up the hill, had a team photo, and we were off!

Despite the signposts, we didn’t get far – we got split up at the first set of traffic lights, shortly followed by a left hand turn which almost half of our group missed. We sent my speedy youngest cousin off to chase them down and she returned dragging along her mum, dad and older sister. Time to regroup! 

The route is almost all on small country lanes, with very little traffic especially for the first hour or so. We were able to cycle several-abreast, to chat, to move forwards and backwards within the group. My uncle even gave me a lesson on riding with no hands and I was so pleased with how long I was able to do it for that I even tried some jazz hands (I haven’t been able to replicate it since though!). 

After the first 15 minutes it began to drizzle and this soon turned into solid rain – although at least it was warm. We decided to stop for a coffee at the next town and reassess the weather then – cycling 100km in pouring rain wouldn’t be much fun. I was really enjoying myself though, despite the rain, and had set my intentions on cycling round the island so I decided I would keep going no matter what!

Eventually however the rain stopped, just as we rounded a bend to see the sea before us and a little village set on steep roads climbing up from the water. We sat outside in the sun for our coffee and nobody had any intention of stopping. On we went! We had a few more drizzling moments but generally it was just moody skies with the occasional glint of sunlight. Everytime I took my jacket off or put my sunglasses on it would start to rain slightly so eventually I decided to stop tempting fate!

We were all very different speeds, from my aunt who had barely done any cycling in recent years, to the two boys who were super-speedy. So although we stopped every few miles to regroup, we tended to cycle in our own little groups, especially given the beginners amongst us weren’t hugely comfortable sticking on wheels. My uncle adopted the approach of just pushing my aunt along instead – it was very annoying to see her whizzing up the hills as I tried to catch Nigel’s wheel!

For me it was perfect though (especially given I knew I had to run 15 miles the next day and so didn’t want to tire myself out!) as, for most of the way I was happy cycling with anyone in the group. It was a fantastic family day out rather than a day to smash it. 

Cycling alongside my sister, having a chat and gently rolling along. Taking the lead up a hill with my cousins on my wheel. Sticking to the slipstream of the boys and pushing hard for a few miles to stay with them. Zooming down the downhills by myself.

And there were a lot of hills – the Isle of Wight is not a flat island and for at least the first half of the cycle it was almost always uphill or downhill and with quite a strong breeze. One hill in particular took us up to the top of the cliffs – a long, steady climb straight into a headwind. We struggled up it and stopped for a breather at the top to let everyone else catch up in dribs and drabs. One of these was my youngest cousin, Jane, who strolled to the top of the climb with her phone out, apparently on SnapChat! 

At least that uphill was followed by an incredible downhill, on a wide, main road  with a great road surface, but quiet of cars. And on the subject of cars – that was the only downside to the whole cycle for me. We experienced so much roadrage, so many angry intolerant drivers. More than I’ve ever experienced on a cycle before. We were a large, not particularly tight group, but we were riding sensibly, indicating, only riding abreast when sensible (for a significant part of the way we were riding on roads so narrow that I wouldn’t have felt comfortable with a car overtaking us unless we were at a lay-by or a wider section of road.

The amount of horns that were tooted at us, cars that sped by far too close on narrow roads when there was a lay-by up ahead. One almost wiped out my cousin who was coming up to a right turn, signalling, moving into the centre of the road. The driver, who was also turning right, seemed to think it was appropriate to try to overtake Joan at that point to get in front of her at the junction. If you’re reading this and you’ve cycled on the island I would love to know if you experienced anything similar!

We stopped at a pub just over half way for a huge lunch and a glass of wine. Lunch stretched out until it was almost 3pm and so we decided my aunt and one of my cousins should take a shortcut back across the island while we continued round it. The pace picked up quite considerably! 

Here we had the best part of the whole day. A wonderful straight road along the coast and then a long, steep climb up directly away from the sea to the cliffs, pausing on the top for a brief downhill followed by another climb. The views from the top were amazing.

From there we soared downhill, a through a few small villages, and then on to a gravel track through the woods – a bit of a shock to us on our road bikes as the rest of the way was on the road! 

We were coming into Cowes, not too far from the end, and people were starting to get tired. I was out of water and very thirsty, stealing sips from everybody else whenever we stopped. The mind is a funny thing – I thought we were almost done as I’d gotten miles and km confused, and I was thinking to myself I’ve got loads of energy, I wouldn’t mind cycling further. Then I discovered we had over 20km to go and all of a sudden all my energy drained away!

There were a few short, very steep hills – the kind that really push up your heart rate and make your legs burn. But the views were still amazing as we soared by the coast.

Finally we reached Cowes where we had to wait for the chain ferry to take across the river, before a final 15 minutes along the main road to the main ferry terminal.

It was a fantastic day out, despite not having the sunny weather we had hoped for. I would love to go back and do it again, a little bit faster next time (and without having the thought of a 15 mile run the next day in my head!). I would really recommend this for anyone – it is hilly but there’s nothing impossible and you can always cut the cycle short at half way as my aunt did. Its generally well signposted – you do need to keep your eyes slightly peeled as a few of the signs are slightly hard to spot behind trees but in general it is fine and there’s no real reason to get lost. As I said above, the only real negative for me was the aggro behaviour of a lot of the drivers!


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