As islands go, it’s fair to say the Isle of Wight probably doesn’t have the wildest reputation.

My favourite fact I heard about the place in the four days I spent there is that it only has a quarter mile stretch of dual carriageway, allowing drivers to really put their foot down and reach 70mph for all of about eight seconds.

England’s largest island has always felt too close to home to be a truly adventurous holiday destination – reserved instead for school trips, tea rooms and retirement homes.

So when I find myself plunging into the onrushing sea from the side of a cliff to get a glimpse of a subterranean cave, it feels like a very un-Isle of Wight experience.

But islands have always had the ability to shock you. There’s something about being exposed on a floating lump of rock away from the mainland that opens the senses to new experiences, new ways of thinking.

Coasteering is perhaps the embodiment of what the Isle of Wight is now trying to be.

This activity is catching on in the west of the island thanks to a company called Adventure Activities.

It essentially involves going for a walk in the sea – literally just strolling out in a wetsuit to see what you can discover.

You are totally out of your comfort zone; ducking in and out of caves, climbing up cliff faces and throwing yourself into the waves.

Even in its traditional pursuits, the island feels a lot more forward-thinking that I expected.

The Oxford Times:

I visit during Cowes Week, the annual August sailing regatta that brings thousands to the island, and surely one of the best times to visit.

As you’d expect, the sailors know how to party and after a hard day’s racing, dozens of pop-up bars along the sea front are packed with people enjoying a hard-earned drink.

The whole thing has a Mediterranean feel where the parties feel like they could go on forever.

Cowes Week brings out the best in the island, even for those who like their feet on dry land, and festivals and events pop up everywhere.

But as with all major events, it also brings crowds, and I stayed on the other side of the Island at The Royal Hotel in Ventnor, as far away as you can get without going into the sea.

The beauty of island life however is that you are never too far away from anything and Cowes is an easy commute from the town.

As you’d expect from Queen Victoria’s favourite holiday destination, the island is blessed with several nice places to stay.

The Oxford Times:

The Royal is very much out of the Victorian era - a grey brick, old coaching house with many windows and an ornate glass entranceway.

It boasts relatively simple but well put-together rooms with views out over the bay and a grand dining room.

For food, it’s all about the seafood and it’s hard to beat a sunset dinner and cocktails at the Smokey Lobster in Ventnor. Here homemade dishes centre around crab and seasonal offerings and the night crowd are well looked-after in chic surroundings.

While we’re on food, the Cow Co in Tapnell Farm is worth a stop-off as is The Yarbridge Inn in Sandown, both of which offer a wide range of traditional foods which are mostly served with a side of great chips.

The great thing about the island is the range of activities, from a garlic farm to West Wight Alpacas, one of the few places in the UK where you can see llamas.

The Oxford Times:

Adgestone Vineyard in the middle of the island has one of the oldest commercial wine cellars in England. Or, for something different, go shooting at Top Targets Tapnell. It will all change your impressions of this familiar, yet surprising, isle.

Setting sail: Taking to the water for Cowes Week

THE yacht lurches to one side and sends us all scrambling for safety again.

If sailing is meant to be graceful, then we’re clearly the wrong crew for the job.

Behind me it’s like a scene from The Titanic, as people attempt to cling to their friends while the side of the boat tips to an almost impossible angle, the railing touching the water below.

Once relatively upright again, the huge great boom swings past, attempting to knock anyone not paying attention into the water.

On the shore the gentler side of Cowes Week is in full swing; the sun is shining, people are sipping Pimms and parading through the town centre in their finest sailing gear.

I’m on board one of the yachts competing in the eight day event, being buffeted by the waves and increasingly thankful for the anti-sea sickness wrist bands I picked up last minute on the mainland.

In quieter moments, staring back at the island or ahead at the boats in front, I think surely this is the only way to experience the world’s oldest sailing regatta.

Yes, the yacht is light-weight and uncomfortable with precious little protecting you from a early bath.

But sailing is an exhilarating and exciting sport where precision is everything and picking the right moment is vital.

One wrong move can send your sail crashing into the water, an error that can mean you never recover your place in the race.

Get it right however and there’s nothing quite like the buzz you feel when the wind catches and the boat is dragged into life, pulling you that little bit closer to the shore.

The Oxford Times:

FACT FILE

  • THE Isle of Wight is easily accessible from the mainland.
  • Red Funnel offers fast and frequent services from Southampton to Cowes on the Red Jet high-speed passenger ferry. Journey time takes 23-25 minutes and return fares start from £9.60 per person.
  • Car ferries operate between Southampton and East Cowes hourly at peak times with a crossing time of 55-60 minutes. Prices start from £42 per car. Dogs are welcome.
  • This year Cowes Week runs from 10-17 August.