Cycling the Isle of Wight’s East Coast | Ryde, Sandown & Beyond

Join me on a full day of cycling adventure on the Isle of Wight, starting from Portsmouth Harbour on England’s south coast. This vlog takes you on a 50-kilometre loop around the island’s east side — with seaside villages, historic landmarks, coastal views, and a ride along the Red Squirrel Trail.

I began my journey in Portsmouth, right on the Solent — the narrow stretch of water separating the mainland from the Isle of Wight. From my hotel, it was a short cycle to Portsmouth Harbour, where I boarded the Wightlink FastCat ferry for the quick 20-minute crossing to Ryde Pier. The ferry ride itself is a highlight, gliding past the Spinnaker Tower and sharing the crossing with fellow cyclists.

Arriving at Ryde Pier Head, you immediately step onto one of the island’s oldest seaside piers, riding straight into the heart of town. From here, I followed the coast east to Seaview, a charming Victorian seaside spot with rock pools, sandy stretches, and sweeping views across the Solent. Sailing boats dotted the water, and the Seaview Yacht Club with its famous Mermaid boats added a touch of maritime history.

The route then passed through Nettlestone and into St Helens, home to one of the largest village greens in England — still used for cricket matches and fairs today. Soon after came Bembridge Harbour and the bustling village of Bembridge, often called the largest village in England. With cafés, pubs, and shops, it’s the kind of place that makes you want to stop and linger.

Leaving the villages behind, I cycled past farmland and Bembridge Airport, before dropping down to the coast at Sandown. With its long sandy beach, traditional pier, and classic English seaside charm, Sandown feels like a step back in time. I paused for an ice cream before picking up the Red Squirrel Trail — an 8-mile traffic-free cycle path that follows a former railway line through wetlands, meadows, and woodland.

The Red Squirrel Trail is one of the best places to spot the island’s iconic red squirrels. Sadly, I didn’t see any this time, but knowing that the Isle of Wight is one of the last strongholds for red squirrels in England makes the ride even more special. Along the way I passed Merstone Station and enjoyed the shaded, flat paths — perfect for summer cycling.

After reaching Newport, I followed the River Medina north on a gravel path, riding past Seaclose Park and the Medina Arboretum, before detouring inland at Island Harbour Marina. At around 40 km, it was the perfect time to stop for lunch, so I dropped into The Cedars pub in Wootton for a well-earned meal.

On the return towards Ryde, I discovered Quarr Abbey, a working Benedictine monastery with a striking red-brick abbey built in 1912. Set among woodland and coastal paths, it’s a peaceful spot to explore, with ruins of the 12th-century abbey, nature trails, and even a farm shop selling local produce.

Finally, I cycled back down Ryde Pier and boarded the ferry to Portsmouth, ending the loop with sunshine, sea air, and that satisfying tired-legs feeling after a perfect day of cycling.

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Tips for cyclists planning this route:
• The Red Squirrel Trail is mostly flat but does turn into gravel in places — a gravel or hybrid bike is more comfortable than a pure road bike.
• Bring snacks or stop in villages like Bembridge or Wootton for food — plenty of pubs and cafés to choose from.
• Keep an eye out for red squirrels, especially near Merstone and in wooded areas.
• Ferries run regularly from Portsmouth Harbour to Ryde Pier Head (Wightlink FastCat). Bikes are easy to take onboard.

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Highlights in this vlog:
• Portsmouth Harbour & Spinnaker Tower views
• Wightlink FastCat ferry crossing to Ryde
• Cycling Ryde Pier into town
• Seaview & St Helens village green
• Bembridge Harbour & Bembridge village
• Sandown seafront & pier
• Red Squirrel Trail ride to Newport
• Lunch at The Cedars, Wootton
• Quarr Abbey visit
• Return ferry to Portsmouth

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If you’re looking for a cycling day trip in southern England, the Isle of Wight is perfect: ferries are quick and frequent, the island is bike-friendly, and the scenery is unbeatable — from seaside resorts to quiet countryside lanes.

I hope you enjoy this ride-along vlog of my Isle of Wight adventure!

🚴‍♀️ Have you cycled the Isle of Wight before? Let me know in the comments — I’d love to hear your route suggestions.

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Chapters:
00:00 Portsmouth Harbour & Ferry
02:30 Ryde Pier Arrival
04:10 Seaview & St Helens
07:00 Bembridge Harbour & Village
10:20 Sandown Seafront
13:40 Red Squirrel Trail to Newport
17:20 River Medina & Island Harbour
20:00 Lunch Stop in Wootton
22:10 Quarr Abbey
25:00 Return to Ryde & Ferry Back