Isle of Wight cycling holidays: top tips for an unforgettable trip Back to top
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A local’s tips for the best Isle of Wight cycling holidays: Q&A with Andy Allen

If you live in the UK and are looking for a cycling staycation, an Isle of Wight cycling holiday is hard to beat.

Branded as bicycle island, cycling around the Isle of Wight is pretty idyllic. We’ve been there a number of times (you can check out our main guide to cycling on the Isle of Wight here), but in this article we delve even deeper and get the inside story from local cyclist Andy Allen.

Andy has lived on the Isle of Wight for nearly twenty years. His parents were born and bred here and he and his brother spent almost all their school holidays on the Island. After finishing University, the Island called Andy back and he lives here with his wife and children. Andy says, “I can’t speak highly enough about our wonderful Island and being a very enthusiastic cyclist, there is just no other way to explore all its beauties”. 

In this article Andy shares his favourite Isle of Wight cycle routes and climbs, as well as his favourite coffee shops and tips for a cycling holiday on the Isle of Wight.

So, over to Andy!

1. Where are you based?

My family and I live in a lovely village on the Isle of Wight called Carisbrooke. It’s famous for its historic castle and is located a couple of miles from the island’s capital town of Newport.  We used to live on the coast in Sandown. I know the whole island very well.

Living in Carisbrooke is wonderful. It’s central to everything and each coastline is only a twenty-minute drive away. It’s also perfect for country walks. 

2. What’s so great about the Isle of Wight for a cycling holiday?

I just love it here. The Isle of Wight is blessed with stunning beaches and is famous for its Jurassic coastline.  If you enjoy village lifestyle, you will also find some of the most picturesque village in the country here.

On bright Sunday mornings, when the family are still fast asleep, I love to get kitted up and head out after a long week at work. There are just so many great rides to choose from, from country lanes to great hills and stunning sea views and coastal paths.

Compton Bay, towards the Dorset coastline

Sunrise over Freshwater Bay

3. What are your favourite Isle of Wight cycling routes?

The Isle of Wight’s bike rides are amazing.

The Island is most famous for its coastal rides. The around the Island route is sign-posted clockwise, or anti clockwise by the Isle of Wight Council, with blue road signs making it easy for visitors who come over to explore. (You can check out our guide to cycling around the Isle of Wight here).

But, when you get off the lovely coast, and start exploring the country roads on the interior of the Island, there is so much more to discover. 

My favourite villages to ride through are Shorwell, Brighstone and through to Brook, Calbourne and the back of Shalfleet.  There are some short punchy hills to tackle and plenty of picturesque villages to pass through.


However, there really are so many villages with similar beauty throughout the island, sometimes, just taking a turn down a road you have never been before is just as exciting and you will always find something of interest to enjoy whilst on your two wheels.  

I have lived here for almost twenty years and I still discover some roads that I have never been down before and think to myself, “why did I not know about this route!”.  The good thing about the Island is that you can do this and will not get lost as being an island you will always come back out on a road or coastline that you are familiar with. Just be prepared to be out longer than you initially planned for so not to miss any wonderful roads to discover.

4. What are your favourite cycling climbs on the Isle of Wight?

There are some great lung-busting hill climbs and I think the most popular one has to be Cowleaze Hill, which is a long drag coming out of the Old Village, Shanklin taken you up to the top of Bonchurch.  Once over, it’s a lovely descent into Ventnor Town centre but one not to hammer down as halfway down, pull over on the viewpoint just to enjoy the scenery.

My favourite climbs are on the south side of the Island.  The Military Road runs right across the back of the Island, from the Famous Blackgang Chine, just a few miles out of Niton, all the way to the beautiful Freshwater Bay and there are three great hills to test your legs.


Going clockwise is my preference, so from Niton to the top of Blackgang is a lovely gentle climb to warm up and again, when you hit the top, the views are just spectacular out to sea.  The descent is good then, few bends to hold your position then once past Blackgang Chine, it’s like a time trial along Military Road for the next 8/9 miles before you hit two more climbs at Compton Bay.   


The next two hills are my two favourites, not too testing but worth pushing yourself and checking your Strava segments after to see where you stand against your friends and others!  The first one must be enjoyed and take a quick rest at the top where I find myself sitting for probably too long sometimes and it lends itself to a great resting spot for a snack. 

Andy in his favourite spot at the top of  Compton Bay

Views of Sandown and Shanklin from           Culver Down

As soon as you descend this one you tackle another short climb but again its one you need to enjoy and look left out to sea as much as you can as on a clear day, there is nothing quite like it and sometimes it’s hard to believe that we are actually in England and not the Mediterranean especially on a beautiful sunny Sunday morning. 


Why do I enjoy these two climbs so much?

It’s really the breath-taking views. Warning though, always check the wind directions before taking the Military Road and make sure you have a tail wind.  West to east is my preference and, with a tail wind, you actually almost feel like you are flying.  But in a head wind, its hard work.  So, on those days I say, go east to west for a much more enjoyable experience!

5. What are your best tips for people cycling the Isle of Wight for the first time?

My best tip for visitors coming across to the Island to explore is to find a central base to start from. In my view, there is no better place to start from than the middle of our Island and Carisbrook is always a popular place and a well-known meeting spot for Isle of Wight cycling club group rides.

The clubs tend to either meet from the village car park opposite the Co Op, which is useful for packing in the last few treats into your pockets before heading out - and there’s also a toilet block there too which is always very handy. You can leave your car in the village car park at a small charge for a day.

Around Carisbrooke there are plenty of nice guest houses and hotels but, to be honest, it does not really matter where you decide to stay when coming over as the island is only 22.5 miles long and 13.5 miles wide.  

If you’re coming with the kids then the holiday parks are great such as The Lakes, Rookley, or Whitecliff Bay, Bembridge.

6. What are your favourite coffee shops on the Island?

The Island has become a cycling haven, especially over the last ten years or so. As a result, small local business around the Island have opened plenty of cycling friendly cafés with bike parking areas. They love to sell you their homemade cakes, which must be tried.  

One of my favourite cafes is the Chessell Pottery Café, a small family run café. They are keen cyclists themselves, so they know what you need and enjoy when having a rest for twenty minutes of so.  It’s located in the stunning West Wight area of the Island offering delicious cakes, light lunches, cream teas etc. and loads of space outside with picnic benches to relax and chat with your friends.  

There are plenty of local pubs too, with large beer gardens, which again make popular resting points.  The Eight Bells in Carisbrook is a great place to finish after a long day in the saddle and also great for the family too. If you’re cycling, meeting your family here at the end of the day is perfect.  

If you’re coming to visit, Ventnor is also an absolute must and make sure you go right down to the seafront and enjoy the tea rooms, pubs and café bars there as the views are just amazing. When you rest up here on a warm sunny day, you could be anywhere in the world.  It always reminds me of the Mediterranean.

Military road, Blackgang Chine to Freshwater Bay

Sunrise over Ally Tower, Appleby, Ryde

7. Is there anything visitors shouldn’t miss?

I could write for hours about the Island and all its amazing ‘nooks and crannys’, picturesque villages with streets lined with thatched cottages and the breathtaking coastal ride from north, east, south and west!

My advice is to plan a long day, or a long weekend starting centrally and go out and explore and see where you end up. Simple.  

However, must-do locations to tick off are The Battery, Top of the Needles on the west tip of the Island, the top of Culver Down on the very east tip of the Island and most definitely the Ventnor ride out through Niton, Blackgang along the Military Road all the way to the Needles.  

But make sure you plan a few stops on route, just to get your camera out of your back pocket to keep a memory of your trip.

8. What’s the best time to visit the Isle of Wight?

I would always recommend coming over from May through to September to make sure you get some of the warmer weather. However, to be honest, if you like winter riding and are lucky enough to pick a day of weekend with crisp bright sunshine, you will not be disappointed.

Big tip though, try an avoid coming over during high winds as many coastal roads are very exposed.  

Also, always check on the web opening times of your planned stops in the cafes or your choice as many are seasonal and also worth checking their opening hours too.  (Nothing worse than looking forward to that cappuccino and homemade flapjack after an hour or so or climbing hills and then getting there to find out they have just closed…Arrrh!)  

9. Final thoughts from Andy

The Isle of Wight is a paradise on our doorstep, easily accessible from the mainland via Lymington, Southampton and Portsmouth. Coming as a foot passenger for the day is really easy as all the ferries cater for cyclists. I hope you have an amazing time here!

Want to plan an Isle of Wight

cycling holiday?

Don’t miss our guide to cycling the Isle of Wight, which includes in-depth cycling routes around the Isle of Wight, GPX, maps and more.

Want to check out some other destinations? For our UK guides, click here - or search by the month you want to travel or cycling destination you want to visit, here.


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