Here’s a project that was close to my heart: cycling around the Isle of Wight with the family! You know how much we love bike adventures with the kids! Cycling around the Isle of Wight is a classic down here in the south of England. The route is about 100km – a satisfying distance. I split the trip into 3 cycling days. We rode clockwise starting from Cowes. Is it a family-friendly route? That depends on your cycle touring experience. I’ll admit, at first I was worried it might be too tough for our Titpuce (12 years old), who’d never done more than 20km in a day before. Ticoeur (14) was in his element. In the end, I came up with a whole plan to make the adventure easier for Titpuce. She took a shortcut on the first day. I’ll tell you all about it. But in the end, I needn’t have worried. Who was the one lagging behind in the family? Me!!!

Day 2 of our cycling tour of the Isle of Wight with the kids

Cycling around the Isle of Wight with the family: Day 1

The ferry journey to the Isle of Wight

Ticoeur and I set off early from Southampton port. We took a ferry to West Cowes on the Isle of Wight with the company Red Funnel. The crossing takes 30 minutes and there’s space for bikes. We paid £56 return for the two of us and our bikes.

Morning ride: Cowes to Bembridge

Once in Cowes, we crossed the village – on foot, as the main street is pedestrianised. After a few pedal strokes, we were already blocked by an inlet. We had to take a chain ferry to avoid a big detour. Finally, the real adventure could begin! At first, the road climbs a bit and it still feels urban. Then it winds through the countryside. Lots of twists, descents, and climbs. The sky was overcast and it was cool – which helped with the uphill sections! More physical than I expected. The wind was quite strong and changing direction. A proper workout!
After a few kilometres, we finally realised there’s a colour code on the cycle route signs: blue on white means clockwise, white on blue means counter-clockwise. Handy!

Around noon, we reached the waterfront at Bembridge and were starving! We enjoyed a lovely waterside lunch at The Best Dressed Crab Limited. Crab, like at home, is a local speciality. Pricey but delicious. We shared a plate between us and topped up with cereal bars before getting back on the road.

Afternoon ride: Bembridge to Ventnor

We headed south. A drizzle starts. More climbs and descents followed.
What were Titpuce and Papa Voyage up to during this time? As I said earlier, I wanted to ease the route for Titpuce. She had a dance rehearsal in the morning – another reason to take the afternoon ferry and use a shortcut: the Red Squirrel Trail. This path cuts across the island almost straight north to south. It avoids many miles. It’s also very peaceful and mostly flat, as it’s a former railway line.

The weather worsened. For Ticoeur and me, the hills got longer and fog rolled in. When the route neared Sandown, we left the official Isle of Wight Cycle Route for a while and rode along the coast on a stretch of the Red Squirrel Trail. The part between Sandown and Shanklin is really lovely:

After the seaside ride, there’s a steep climb near Shanklin Shine up to the old village of Shanklin (Shanklin Old Village). Ticoeur often had to wait for me at the top.

Old Shanklin, Isle of Wight

A few more miles and we reached the hills above Ventnor. Beautiful green views – slightly misty and damp 🙂

Arrival and family reunion in Ventnor

We arrived at our first accommodation, down in Ventnor village. Papa Voyage and Titpuce arrived 15 minutes later. Great timing! We reunited, all soaked from the rain. Our place was a lovely little apartment with charming decor. Good value for the Isle of Wight. There was also a nice DVD selection. The kids picked Les Misérables to watch.
We headed out again to a lovely seafront pub: The Spyglass Inn. A great, characterful pub! But it was pouring!

Day 1 Cycling Summary:

• 45km for Ticoeur and me
• 30km for Titpuce and Papa Voyage

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Cycling Around the Isle of Wight as a Family: Day 2

Morning: From Ventnor to Chale

We set off early, all four of us. The blue sky is back! What a boost!

We see Ventnor beach again under the sunshine!

Off we go! A long, fairly steep climb awaits us.

As usual, I’m lagging behind on the climbs while Titpuce powers ahead! At the top of a long hill, we take a Mikado break (brought from France). Then, the climb continues! Titpuce and I walk a few hundred metres.

At the top, we have a fantastic view and perfect weather to enjoy it!

Well-deserved lunch break at the pub The Wight Mouse Inn. Their garden is lovely, with a sea view. We order tea and pies. There’s also a play area for younger kids, though Titpuce enjoyed it too. I had wanted to book a night there, but it was fully booked. Also, based on the length of our cycling days, it would have been too early. But depending on how you divide your journey, it could be a good option, so here’s the link to their hotel section.

From Chale to Freshwater Bay

After the pub, we cycle for an hour on narrower, quieter roads. It’s nice not see any cars, even though British drivers are really careful and respectful towards cyclists.

We then return to the main road for the last stretch of the day. There are some cars, but the views more than make up for it. A few more big climbs, and then we reach Freshwater Bay beach.

A few minutes further on is our accommodation for the night: 9 Afton Barns. We booked this very traditional house with a typical English interior. Not really our style, but it’s very neat and spotlessly clean. A good spot inland, not far from Freshwater Bay beach.

We drop off our bags and set off… Hiking!

The Needles:

Yes, I wanted to walk after all that cycling! We pedal a few minutes to the start of a two-hour hike on the western tip to admire The Needles, those little chalk stacks that symbolise the Isle of Wight. It’s a slow but steady climb and we’re facing the wind. The view of the Needles is lovely.

Tonight, we’re skipping the pub so Papa Voyage and I cycle to a supermarket. Pasta party at our rental! The kids are thrilled! And the good weather is back!

Day 2 Cycling Summary:

35 km with lots of elevation!

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Cycling Around the Isle of Wight as a Family: Day 3

With the hardest day behind us, we calmly begin the 3rd stage of our cycling trip—and even add two detours!

From Freshwater Bay to The Needles:

We don’t set off until 10am. Not far from our accommodation is the Piano Café, where we had breakfast on a previous trip to the Isle of Wight. Highly recommended!

Heavy rain begins, but the wind quickly brings back the sunshine—phew!

Our first detour today is to return to see The Needles. This time via the cycle path. We have our National Trust membership, so we can enter the viewing area for a closer look—but honestly, we preferred the free clifftop views from yesterday.

 

From The Needles to Yarmouth:

We get caught in another heavy downpour! Thankfully it’s short-lived. The sun reappears as we follow a lovely estuary. The path is flat. Very relaxing!

We arrive in Yarmouth, a charming little village. We stretch our legs by walking along the pier before getting back on our bikes.

Then we make a detour for lunch at the island’s best restaurant: The Hut! A fantastic spot for seafood lovers. The setting is stunning too, with sea views. Note: bookings are needed one to two weeks in advance.

Heading to Cowes: The Loop Completed!

Next stop: Cowes, our third accommodation. On the way, we experience very changeable skies, climbs and descents, and plenty of woodland—but sadly, still no sign of the famous red squirrels of the Isle of Wight!

Here’s Cowes! The loop is complete!

We had booked two rooms in a homestay: see Cliffside in Cowes. The host was lovely. He was happy for us to dine in his garden (we quickly bought salads at the supermarket). He also provided tea, coffee, cereals, etc. for breakfast.

Our host suggested one last bike ride along the seafront to a pub with stunning sunset views. We celebrated the end of our cycling tour around the Isle of Wight!

Day 3 Cycling Summary:

• 50 km including 20 km of detours!
• In total, over 3 days, Ticoeur and I cycled 130 km (the official loop is 105 km, but we added lots of extras).

All in all, it was a sporty adventure! Don’t set off without prior experience. It’s better to have done several cycle touring trips first. This route isn’t the easiest—very hilly and shared with cars. But if you’re used to family bike trips, the Tour of the Isle of Wight is a fantastic journey full of great memories!

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Visit to Osborne House

We could have taken the ferry back to Southampton last night from Cowes, but we wanted to enjoy the evening on the Isle of Wight and revisit Osborne House, which we’d seen a few years ago. It’s Queen Victoria’s summer palace. Absolutely stunning, with a rich interior and an impressive Indian-style dining room. The visit took us all morning. Osborne House is located 3 km from Cowes, so just a short bike ride (around 25 minutes). You could also fit this visit in on Day 1 of your cycling tour. Allow at least 2 hours to explore the house and gardens.

Before taking the ferry, we grabbed sandwiches in Cowes from Manny’s Baguettes. Perfect and affordable!

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Tips for Preparing Your Isle of Wight Cycling Tour

• Getting to the Isle of Wight: We took the ferry from Southampton, but there are also boats from Portsmouth. If so, you’ll arrive in Ryde.
• Planning the cycling stages: The cycling section on the Visit Isle of Wight website is excellent. You can even track the elevation and distance by moving your mouse along the route. See Round The Island Cycling Tour. For the Red Squirrel Trail, Papa Voyage and Titpuce followed the path from Cowes to Ventnor without doing the full loop. See the route. We chose a clockwise direction because it was more convenient for our accommodation and the shortcut on Day 1 via the Red Squirrel Trail.
• In our bags: We packed windbreakers and rain capes—essential! Papa Voyage and I each carried a large bag with everything for the family. Don’t forget lots of spare socks—very comforting when it rains! The kids didn’t carry anything. Papa Voyage also had a small repair kit for the bikes. Be sure to bring sunscreen, water bottles, and snacks for everyone!

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So, who’s tempted by cycling around the Isle of Wight?