Dream drives: Isle of Wight

| 10 Jan 2022
Classic & Sports Car – Dream drives: Isle of Wight

For the latest classic car news, features, buyer’s guides and classifieds, sign up to the C&SC newsletter here

No doubt many enthusiasts, not least several members of the C&SC team, were lamenting the cancellation of the Le Mans Classic in 2020 and 2021.

That early start, the motorway thrash down to Dover, and the chilly wander among the parked cars queuing for the ferry with a fizz of excitement in the air… all rituals sadly missing from the summer calendar.

In the absence of foreign adventures, we decided to get our ferry fix with a day trip to the Isle of Wight, an often overlooked destination just off the south coast that, despite its diminutive size, offers a mix of stunning scenery and engaging driving roads that could have been created with the British classic in mind.

Classic & Sports Car – Dream drives: Isle of Wight

With no passport controls or customs checks the ferry crossing is a delight, in our case taking us from Portsmouth’s old town to Fishbourne on the island’s northern shore, from where we decided to track a circuitous clockwise route along the coast.

Turning left out of the port takes you into the town of Ryde; carry on and the residential backdrop gradually gives way to rolling countryside as the road twists and turns past Nettlestone towards Bembridge.

The harbour is a treat, with boats bobbing at their moorings just metres from the road, and boatyards and restaurants lining the way.

The Best Dressed Crab reputedly sells one of the finest crab sandwiches on the island.

Classic & Sports Car – Dream drives: Isle of Wight

The road weaves upwards as you turn south, taking in a pleasant series of bends on the way to Shanklin, passing in the shadow of Bembridge Fort with its incredible views of Sandown Bay.

The resort’s main attraction is its beachfront, which is reached via a steep, snaking road meandering downwards towards the waterline.

At the bottom, the rows of colourful beach huts make a great backdrop for a photo, and a nice spot for a walk on the sand before slotting it into second and cruising the esplanade with its packed bars and restaurants.

Classic & Sports Car – Dream drives: Isle of Wight

Climb past the Barrack Battery and head out of town on Church Road for a fabulous set of winding sweepers – the first time you can really put your foot down – and take in a panoramic view of Steel Bay.

Ventnor awaits, the Victorian resort town nestled at the foot of cliffs with a microclimate all of its own.

The Botanic Gardens are worth a visit if you stop, otherwise dial west past St Catherine’s Oratory – a medieval tower built in penance after the landowner pilfered wine from a shipwreck – and the fabulous Military Road (A3055), built in 1860 as part of the island’s defences.

Classic & Sports Car – Dream drives: Isle of Wight

The road spans the southern section of the Isle and, while it isn’t a particularly challenging drive, it offers some breathtaking vistas of the Channel.

After cresting its highest point, the road dips downwards towards Freshwater, a picture-postcard setting against azure seas and chalk-white cliffs.

Take the single-track road to The Needles, a formation of rocks jutting out into the Solent, before turning north and crossing the bridge road at Yarmouth.

Classic & Sports Car – Dream drives: Isle of Wight

Cut east and hang a left on to Whitehouse Road, following it north until you reach Cowes on the west bank of the River Medina.

In August the town comes to life for the annual Cowes Week regatta, but even in the off season it’s a great place to pick up fish and chips before the short run back to Ryde and the ferry home.

If you have time to spare, take a turn around the gardens of Osborne House, Queen Victoria’s beloved summer retreat. 

Images: Max Edleston

Local knowledge

  • Where to stay Tom’s Eco Lodge: offset those hydrocarbons in a green cabin
  • Where to eat TZ True Food: beach café on the Isle’s southernmost tip
  • What to see Isle of Wight Bus & Coach Museum: free family fun in Ryde
  • Hidden gem Appuldurcombe House: reputedly the island’s most haunted building, in Wroxall
  • Pitstop Freshwater Garage: a friendly Gulf station well stocked with the essentials

All information correct at date of original publication


Dream drives: B4425, Burford

Saloon bar brawn: Rover P6 3500S vs Triumph 2.5 PI MkII

Estates of mind: Triumph PI Estate vs Range Rover