Isle of Wight – A Weekend Cycling Adventure

I look like a chocolate cake melting in the sun. My mouth is hanging open. I am panting so hard that the sound of my breath vibrates in my ears with perspiration dripping from my helmet and onto my hands. Sarah and I are cycling the Isle of Wight. We’re tackling one of the longest cycle ascents I’ve ever done from Blackgang to Freshwater, on one of the hottest weekends of the year!




With the Friday off work, we had 3 days to explore the Isle of Wight. I cycled over to Wimbledon, the nearest mainline rail way station to me. Whilst on my bike, there is a twinge of nervousness. I picture a red-faced, angry train guard, ticket barriers to lift my bike over and the glare of fellow commuters who dislike anything that takes up more space then a pair of feet planted to the ground. Sigh. I hope I’m allowed on the train. I wish the UK public transport systems were more cycle friendly.


Keeping out of the way at Wimbledon Station



I booked my train ticket 3 days in advance and got a great fare of £13.50 return (with a YP railcard). Upon arrival at Portsmouth Harbour, it is very easy to get to the ferry port with a bike. The ferry port is attached to the train station. You descend down a long, wide ramp to a waiting area for Wightlink.  Bikes can be carried free of charge onto the ferry and there is a dedicated room to keep your bike in. I leave Bluey (my bike) downstairs and we ascend to the sun deck.

The sea was buzzing, the sun was beating and we smiled from ear to ear with pure excitement. With no route planned, we had no idea where we would end up that evening!



Bike: From the ferry pier, it was a short walk to the Town Centre in Ryde. We rented a bike for Sarah from TAV Cycles, the bike hire was only £25 for 2 days.

Map: TAV Cycles had a supply of ‘Round the Island’ cycling maps. The whole 70 mile route was signposted and we used the map as a brilliant point of reference for our adventure. We only used our phones only a couple of times when we lost the ‘Round the Island’ signs.

Lock: The bike shop also supplied us with a bike lock, spare inner tube and mini bike repair kit. The guys working there were brilliant and passionate about bikes.

What did you bring? We brought a small backpack each with some clothes, swimwear, a toothbrush, sun-cream and a bivvy bag to sleep in. We left one bike lock at the shop and shared one to save carrying weight around the island.


Our battered map after a summer weekend of cycling!


Day 1: Ryde to Chale (approx 25 miles / 4 hours cycling). 

We set off from the bike shop around 3:00pm, hopeful to reach Ventnor by the end of the day. Having not been to the Isle of Wight since childhood, I was in awe of how beautiful the island was. We cycled pass golden crescents of sandy beach, Edwardian villages and colourful boats moored in turquoise blue sea. From the very moment we set off, cycling the Isle of Wight provided hill after hill to test our legs! Every ascent was followed by an adrenaline inducing freewheel down. Capture

We stop off at Shanklin, a charming seaside resort with a sandy beach. With time off the saddle, we order a decadent selection of cooling mint ice-cream and a scoop of rocky road encased in a waffle cone. With the crunch of biscuit and melt in the mouth fudge pieces, nothing more could contribute to a perfect summer’s day then ice-cream on the beach after a long bike ride.


We mount our bikes again with the sun dwindling in the horizon. With a creased map in hand, a female cyclist saw us hesitating over directions. She asked us where we were trying to get to and went out of her way to lead us to the best route. After a left, right, left and another left we reached a hidden forested trail. We would’ve never found this on our own and we thank her over and over again for her help.

With a couple more hours cycling, we reach Wight Mouse, a stone built inn with hearty meals and sea views. Our initial plan was to bivvy bag the entire weekend. We didn’t release how foolhardy this would be. To combine long cycling days and restless nights would’ve taken the ‘fun factor’ out of our weekend adventure.


At Wight Mouse Inn, the staff recommend us accommodation called Butterfly Gliding. Situated just a short bike ride away, we meet Dave’s family and his young daughter jumping on a trampoline. We explore extensive gardens with bell tents, vegetable patches and a sofa taking in spectacular cliff-side views. We notice a ‘secret trail’ to a secluded beach. We both know that we’ve found where we want to stay for our spontaneous nights sleep. In the evening, we chatted to Dave’s daughter, showered to a more presentable state and met an American family who were road tripping the UK.


Day 2: Chale to Cowes (approx 28 miles / 6 hours cycling). 


The next morning, Sarah and I wake up early to explore the secret trail down to the beach. Consisting of a steep drop down to the trail, we bum shuffle down a sandy slope and follow the trail to the beach. The path is marked by small blue ribbons as occasional path markers. With a last rocky scramble, we ran straight into the sea with a whoop of delight, an emotion akin to what the protagonist in Alex Garland’s The Beach would’ve felt. There were a couple of occasions where we thought of turning back due to the steep drops and we were happy to have made it to the secret beach.


Our 2nd day of cycling is from Chale to Cowes. We were aiming for Newport as an end destination. Our highlights today is a visit to Compton Bay. The bay was a two mile stretch of contrasting golden and dark sands, with rolling seas and tumbling multi-coloured sandstone cliffs. There were the white chalk cliffs of Freshwater in the distance.


After our long ascent up Military Road, we descend into Freshwater and proceed to Yarmouth. With a stunning 17th Century church and cobbled streets, we stop off at a The Gossips Cafe for one of IOW’s most famous delicacies, crab!


From Yarmouth, we cycle through the Hamstead Heritage Coast, a series of marshy wetlands and quiet estuaries which were a haven for wildlife.


Upon arriving at Newport, we realised that the Round the Island Yacht Race is on that same weekend and all accommodations were fully booked in Newport. We find a delightful Air bnb in Cowes, situated just a 30 minute bike ride away on the Red Squirrel Trail. 


The air bnb was owned by Brian and Caroline Hicks, the proprietor’s of Harbour Kitchen Cafe in Cowes. We were happy and felt lucky to find such a last minute room.


Cowes had a festive and lively atmosphere following the end of the Yacht Race. We went to a local chippy for a celebratory meal of vinegary chips and hot homemade fish cakes!

Day 3: Cowes to Ryde (approx 10 miles / 1.5 hours cycling). 


Our last day was a leisurely ride to take the ferry back to Portsmouth in the late afternoon. We took the chain ferry from Cowes to Eastern Cowes and rode through to Fishbourne. We returned to Ryde to return the hire bike for 2:00pm.

To finish our cycling adventure, we had a free afternoon to relax on the beach before our ferry and train home to London.


Top Tips

  • Transport: Book your train tickets at least one week in advance of travel, we managed to book a return to Portsmouth (from London) for only £13.50.
  • Transport: I used Tesco Clubcard vouchers for my ferry ticket. £7.50 in vouchers allowed me to obtain a return ferry ticket without paying anything on the day. You can also get a discount on the ferry crossing by booking in advance, or by purchasing a ‘train ticket’ from Portsmouth Harbour to Ryde Esplanade (this gives you 33% off the price if you have a railcard).
  • Blog: Sarah’s Blog is available here 
  • Activity Level: Leisurely. Although 70 miles of undulating hills seems like a challenging weekend away, we didn’t race and had a regular stops. I would say that the itinerary can be done by anyone who is happy to ride a bike.
  • Accommodation: We initially planned to bivvy bag to make it the ‘most spontaneous adventure ever’. I would advise that the idea of bivvy bagging after a long cycling day wouldn’t make people happy. We booked Air bnbs and accommodations the same day each time (July 2018, just before the start of the school holidays).
  • Cost: The whole long weekend away with ferry tickets, accommodation and train tickets was approximately £120 per person.
  • Bring your own bike? It worked well for me to travel from Wimbledon with my bike. With Sarah living in Finchley, it would’ve been tricky for her to navigate London roads with a bike and a backpack.
  • Food: We brought some cereal bars and two bottles of water. Gossip’s Cafe did a wonderful crab salad and Tottie’s fish and chip shop provided a great hit of vinegary, hot goodness on our penultimate night.
  • When? We learnt that Ventnor is on average, 5 degrees warmer then the rest of the UK. Anytime from April to October is a great time to embark on this weekend adventure.
  • Questions? If you have any questions about organising this, please feel free to comment here or email me and I’ll be happy to help.


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