Take a trip to the Diamond Isle

by MotoGusto Editor

With planned motorcycle touring abroad ruined for many this year, o75 crossed the waters to explore the roads of the Isle of Wight instead.

2020! What a year to be sitting at home with the bike in the garage during lockdown. With touring plans shelved and client schedules sliding around like wet kippers on a fishing boat’s deck, I had little chance to escape the clutches of my desk. Then, a glimmer of hope – one solitary day and an urge to cross some waters; my eye was on the Isle of Wight. With ferries only operating essential travel services, news soon came through that restrictions were being lifted. I parted with £45 and booked my Wightlink day-return ticket. Huzzah!

Partnering with my touring buddy, Calimoto, I planned two routes on my laptop that evening. Then, coincidentally, the day before I left, I heard about the Diamond Races. Intrigued, I read more about the island’s new TT-style road race event to take place in October 2021. I just had to ride the 12.4-mile circuit, so put that into Calimoto too.

Wightlink’s Hybrid Victoria of Wight

Arriving at the IoW ferry in Portsmouth at 8am, the Victoria of Wight – Wightlink’s Hybrid double-decked ferry – started loading soon after. Embarking, I left my bike on its side stand, in first gear, then grabbed a coffee to enjoy the crossing. With the sun shining, the shimmering, calm, blue seas soon lifted my soul before jumping back on my beast 40 minutes later.

Calimoto loaded, I rolled off the ferry and, within minutes, I was experiencing Firestone Copse Road’s twisty offerings, the sun glistened through the trees as I headed to my first target – Ryde Pier; a pier you can ride on. Its timber-planked promenade accompanies you to the end; I would think twice if it was wet.

Follow o75 taking to the roads of the Diamond Isle

The day warming up, next stop was St. Helens which cups Bembridge Harbour and many of its houseboats.
Heading along the B3395, Bembridge Airport appeared from under the trees soon followed with a worthy view and a decent run-up Sandown Road.

Through Yaveland and Sandown – there’s plenty to do here for the touring visitor, or head a little further through Lake and Shanklin (just eight miles from Ryde), quintessential thatched buildings line the side of the road. However, I was here for the ride. Continuing with the coastline route, the beachfront town of Ventnor would be another good stop (I would find myself coming back here later that afternoon).

Riding along the southern-most tip towards Blackgang Chine offers up a cracking stretch of road down into Chale – and the route of the Diamond Races. I decide to pull into a car park behind a Scout Hut and tune Calimoto into the road-race route.

Diamond Races

Diamond Races route

12.4 miles and 20 minutes of pure riding bliss – well that’s what Calimoto was telling me. Running in an anti-clockwise direction, the first eight miles or so would be country roads nipping through a few villages along the way including Chale Green, Shorwell, Limerstone and Brighstone. It’s got a few tricky corners and tight junctions. It then drops onto Military Way for the five-mile run back to Chale. We could see riders exceed 180mph along its practically straight road – but watch for the kinkiest of kinks about two thirds along! I suspect the Chale Recreation Ground could be where we see the start/finish line and the paddock nearby.

Back behind the Scout Hut, to retune into the third route of the day along the westside of the island, I head back and westwards along Military Road towards Freshwater Bay. This is one of those gems of a road. Long straights running parallel with the crumbling coastline and white cliff tops coming into view in the distance, with the blue channel lapping at its feet. I could do this road a few times, that’s for sure. Dropping down into Freshwater, an adjacent car park would make for a brew stop.

Military Road – a jewel in the island’s crown.

I continued with the island’s coastline with my eye on the Needles and Alum Bay only to turn back with payment parking ahead. I only hoped to stop for a few moments. Back into Freshwater Bay, Calimoto led me to The Causeway then onto Yarmouth with Wightlink ferries connecting with Lymington, south of the New Forest. As I rode along Yarmouth’s waterfront, I appreciated what this island had to offer, and there was still plenty to come.

It was probably a good time to let Calimoto off its leash to conjure up another bag of cracking inland roads, and it wasn’t to disappoint.

Continuing east on the A3054 through Shalfleet, I turned north up Corf Road towards Porchfield, a cracking bit of tarmac for any motorcyclist before stopping for lunch at The Sportsman’s Rest. With a full belly of fish and chips, I headed to Cowes and its Chain Link Ferry, but I realised I had no cash. A quick £1.70 debit card payment on its website and I arrived to find the service suspended! Well, that’s £1.70 I’m unable to use. The long way round it is! It was probably a good time to let Calimoto off its leash to conjure up another bag of cracking inland roads, and it wasn’t to disappoint.

Route ready, I rode southeast towards Downend. With the countryside opening up, Calimoto led me to Merstone and Godshill; and its famous model village.

Zig Zag Road – yes, really!

From there, next stop. Ventnor, with its cascading roads descending to the beachfront, one street name caught my eye: ‘Zig Zag Road’ – really? Intrigued, I turned back to zig-zag as I made my way down. Do aim for Shore Hill – a little surprise is in store. Parking is available at La Falaise Car Park or carry on up the 1:4 increment up Bath Road – certainly a little skill is required here; just don’t stop or stall.

Ventnor – an ideal spot to stop

Heading back on roads covered hours earlier, I picked up Whitwell Road before crossing over via Kingates to Niton Road – another top road for me that runs up to Rookley. Turning left down Highwood Lane to Chillerton, roads continued to embrace my enthused riding.

The road surface is sublime

Through Billingham then back onto the Diamond Races route once again, I reach Brighstone, then onto Lynch Lane. The roads twisting and climbing up and over, travelling under an abundance of trees to Calbourne. Turning right along the Newport Road through Carisbrooke, stopping for fuel, I picked up a route through Havenstreet encountering a police roadblock forcing a five-minute diversion riding through Arreton, Langbridge and Rowlands Lane instead. Then it was one last hurrah riding Firestone Copse Road once again heading back to Fishbourne for the 40-minute crossing to Portsmouth.


Throughout the roads are smooth, the ride sublime, it’s a surprise why I’d never thought of heading to the Diamond Isle – it really is. I thoroughly enjoyed it. It will provide a great taster for anyone touring for the first time – it’ll undoubtedly whet appetites. Pop over for a day, or stay for a weekend; there’s plenty to see and do with accommodation in abundance. If the weather looks iffy, or wish to leave the camping gear behind, grab a static caravan. Either way, you can ride for as long or as short as you wish, knowing your stay is never too far away.

#isleofwight #diamondisle #wightlink #wightlinkferries #o75 #motogusto

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