Isle of wight: A week of Cliffs, Kindness and Cows

After months of churches, mosques, temples and castles, I decided my next adventure needed to be something different — something outdoorsy, close to home, and ideally not involving stairs to a bell tower. With my newly‑acquired IBS demanding a bit more dietary control, the Isle of Wight coastal path felt perfect: 78 miles in seven days, challenging enough to feel proud of, but not so extreme that I’d need a medal at the end. I also treated myself to luggage transfers, because carrying a giant pack is overrated.

A Kind Start in Cowes

My first stop was West Cowes, where I wandered into a fish restaurant at the same moment as a retired couple. When they heard me ask for a table for one, they immediately invited me to join them. I accepted — and what a lovely evening it turned out to be.

They were retired Met Police officers who had lived in Hong Kong, full of stories and clearly still fuelled by adventure. They were celebrating their wedding anniversary on the island. At the end of the meal, I popped to the loo, returned to ask for the bill… and the waiter told me they’d already paid. I turned to thank them, but they were already waving from the door before disappearing into the night like two very benevolent escape artists.

It was such a generous gesture — the kind that reminds you the world is full of good people. I’ve vowed to pay it forward one day.

Day One: Shalfleet Warm‑Up

The next morning I set off for Shalfleet, an easy eight‑mile warm‑up. I’d only visited the Isle of Wight once before for work, so I was curious to see if my positive first impression would hold.

Ancient woodland led me towards Shalfleet, and I somehow managed to get more insect bites in one day than I did in 45 days in Greece. A stop at the National Trust hide in Newtown paid off spectacularly — I spotted one of the recently released white‑tailed eagles. The whole day was full of birdsong and countryside nostalgia.

I spent the evening in Ningwood, eating steak and chips in a local pub. My new FODMAP diet meant this became my default meal for the week — not exactly thrilling, but every B&B I stayed in went out of their way to accommodate my food needs. They were all incredibly kind.

Day Two: Lunch With Unexpected Company

I stopped for lunch in a quiet field surrounded by woodland, happily perched on the ground with a tin of mackerel and some salad bits. I was gloriously content… until a herd of cows appeared around the corner. I grabbed my things as gracefully as one can while holding tinned fish and ran for it.

Clifftops, Sunshine and the Longest “12 Miles”

As the week went on, the clifftop sections increased and the weather stayed perfect — around 20 degrees and sunny. Day six, from Freshwater to Niton, was the toughest. The instructions claimed it was 12 miles; it was actually 16, thanks to diversions caused by coastal erosion.

Miles 12 to 16 were tough, and even the short walk from my room to the bar (for yet another steak and chips) felt like an expedition. But Freshwater Bay was gorgeous, and I had a wonderful meal overlooking the sea. The walk to the Needles was stunning, especially with the sunlight bouncing off the water.

The end of day six led me to meet a new Mark, who stole my heart.  A beautiful black Labrador guide dog whose owner was in the next room to me.

The Final Stretch: Rain and Red Squirrels

The last day was wet — relentlessly wet — until the final two miles, when the sun finally appeared and dried me off. The rain did have one perk: it brought out the red squirrels, busy collecting acorns and darting around like tiny woodland acrobats. I’d never seen them before, and they were absolutely charming.

Final Thoughts

I’ve loved my time on the Isle of Wight. It’s quick and easy to reach from London, full of beautiful countryside, and packed with things to do. I even indulged in a seaside arcade and would absolutely have played crazy golf if I’d had a travel companion with me.

I’ll be back — maybe next time I’ll cycle the island or explore more of its historical sites. For now, it’s home for 36 hours to repack before heading to Norfolk for some kayaking and some work on my CV, sooner or later I will need to return to work.