• Distance 35 km
  • Elevation gain 600m
  • Difficulty
  • Epic rating

This is a short ride that packs a big punch.

It gives you a superb feel for the south of the Isle of Wight, passing through two of the island’s best-known towns, as well as quiet countryside, beautiful Victorian villas and expansive coastline vistas.

It may only be 35 kilometres, but it includes in 600 m of climbing. You can reduce this by skipping two of the three main climbs (one is an an out and back to St Catherine’s lighthouse, the other is an out and back up Ventnor Down) – though you’ll miss two of the best bits of the ride!

All metrics in this article are approximate.


Rew Road between Ventnor and Wroxall and the descent from Shanklin to Ventnor are both really enjoyable. They’re easy going, and the views are quintessentially English.

Appuldurcombe House is an unforgettable sight, especially if you visit after hours and have the place to yourself, as we did.

Golden sands with bicycle in front of railings at Ventnor esplanadaIf you’re feeling strong, head down to Ventnor Esplanade. The climb back up is tough though – 25%!
The impressive sight of St Catherine's ligthouse painted white against the blue seaSt Catherine’s lighthouse
Beautiful Victorian villas facing the sea near VentnorYou pass classic Victorian villages on the road to Niton

Route notes

1. Ventnor to St Catherine’s Lighthouse and Niton

It’s a lovely ride out to Niton, with glimpses of the sea to your left and only a few steep kick-ups to keep you on your toes. You pass the Botanic Gardens before coming into picturesque St Lawrence, with its beautiful stone church and Victorian villas overlooking the sea.

After St Lawrence, there have been several landslips which have caused short sections of the road to fall away. These sections have been replaced with a bridleway, which we found perfectly passable by road bike.

When you meet the turning to St Catherine’s Road, choose whether you want to head down to the Lighthouse or continue on around to Niton. There’s more information on the road down to the Lighthouse in our Lighthouse, Needles and Downs route guide.

Note: If you want to make the first few kilometres tougher, take a detour down to Ventnor Esplanade. It’s very pretty with its art deco buildings and sandy beach, but beware the gradients on the way back up – road signs claim 25% (see the photo below)!

Alternatively, if you’re short of time, you can cut off the loop and head up Seven Sisters Road and St Lawrence Shute instead.  But beware, Seven Sisters Road is pretty brutal.


2. Niton to Wroxall

Once at the top of the climb, just before Niton, the road back towards Ventnor is a sweeping downhill with pretty views down to the town.

It’s then decision time: whether to ride up (and then back down) Down Road and take in Ventnor Down. If you’ve got the legs, you should definitely do it! The views from the top are glorious and if you’re into crossing things off lists, it’s a ride that appears in Simon Warren’s Another 100 Greatest Cycling Climbs.

You weave out to the countryside again and take a left onto Rew Road, part of the signposted Round the Island route. This is a real highlight. It takes you through quiet fields and pretty farmhouses; quintessential English countryside at its best.

If you decide to take the short detour to Appuldurcombe House, you are in for a real treat. This was one of our favourite places on the Island.  Once the grandest house on the Isle of Wight, it is now a shell, but a very special shell. You can walk around the empty rooms and enjoy the lovely grounds and views. It is free to visit.


3. Wroxall to Shanklin

In Wroxall, you have two options: either take the disused railway line or the main road. The railway line is part of the Red Squirrel route and has a hard surface that we found suitable for road bikes when we were there. It’s really attractive, passing under a number of bridges and open countryside. Of course, it’s also lovely to have zero road traffic.

But if you’re worried about punctures, stick to the main road. It doesn’t add much to the journey and is on the BB3327 and the A3020.

Our GPX route opts for the Red Squirrel route.


4. Shanklin to Ventnor

Once you’ve cleared the chocolate-box thatched cottages of Old Shanklin, you start climbing up, up, up. The views back to Shanklin are superb and, once you make it to the summit, it’s a fun descent back to Ventnor, with superb views across memorably green and verdant fields dotted with sheep and trees.


Appuldurcombe house, a ruined mansion in the Isle of Wight, at duskAppuldurcombe House
25% sign near the esplanade in VentnorIf you go down to Ventnor Esplanade, be prepared for 25% gradients on the way back up Bath Road (see section 1 of ride log above for more info)!
A series of doorways inside Appuldercombe houseInside Appuldurcombe House near Wroxall

Café stops

Given this is a short ride, you may not need a café stop. But if you do, the villages you pass through should be able to help.

Niton and Wroxall both have a pub and small shop, while Shanklin and Ventnor both have an array of pubs, cafés, shops and restaurants. If you head down to St Catherine’s Lighthouse, you’ll also pass The Buddle Inn.


We rode this route from Bonchurch.

Check out our accommodation suggestions in our article on cycling accommodation on the Isle of Wight.


Read our tips for cycling the Isle of Wight before you set out.

Found this guide useful?

  • We’d love to hear from you – comment below or drop us a line.
  • Don’t miss our other ride guides on the Isle of Wight: see the related rides section above.

Check out our ultimate guide to cycling the Isle of Wight and other articles, below.


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Clare Dewey

Clare Dewey is a cyclist with a passion for travel. She set up epicroadrides.com in 2018 to help make it easy for cyclists to explore the world by bike. Today her mission is still inspiring cyclists to discover new places on two wheels – and doing what she can to make sure they have the best possible time while they’re there. Clare has visited 50+ destinations around the world, many of them by bike.

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