The Isle of Wight offers one of Britain’s most perfectly formed cycling adventures—a compact 70-mile circumnavigation packed with breathtaking coastal scenery, charming villages, and historic sites. Our 3-day itinerary breaks this iconic route into manageable segments, highlighting the best accommodations and attractions along the way.
Why cycle the Isle of Wight?
The island’s Round the Island route follows quiet lanes and dedicated cycle paths, with stunning sea views around virtually every corner. As Britain’s sunniest spot with a unique microclimate, it offers ideal cycling conditions from early spring through late autumn.
Day 1: Ryde to Freshwater Bay (25 miles)
Starting point: Ryde
Your adventure begins in Ryde, easily accessible via ferry from Portsmouth or Southsea. The town’s elegant Victorian architecture and long sandy beaches make it the perfect launching point.
Before You Ride: Visit Wight Cycle Hire if you need any last-minute accessories or advice from local cycling experts.
The route: East to West Coast
Today’s ride follows the island’s northern coastline before cutting south to the spectacular west coast:
- St. Helens – A picturesque village with a charming green
- Bembridge – Home to the island’s last remaining windmill
- Sandown – A traditional seaside resort with a magnificent sandy beach
- Shanklin – Don’t miss the picture-perfect Old Village and Chine
- Ventnor – Built on steep slopes of the Undercliff with Mediterranean vibes
- Blackgang – Offering dramatic coastal views
The route includes some challenging climbs, particularly as you approach the island’s southern coast, but the views make every climb worthwhile.
Lunch Stop Recommendation: The Garlic Farm near Newchurch offers cyclist-friendly lunches featuring their famous garlic-infused dishes.
Evening destination: Freshwater Bay
End your first day at stunning Freshwater Bay, where white chalk cliffs frame a perfect crescent beach. The area offers breathtaking sunset views over the English Channel.
Where to Stay: Freshwater Bay House offers comfortable rooms with sea views, secure bike storage, and excellent dining. Their “Cyclist’s Package” includes energy-rich breakfast and packed lunch options.
Check availability at Freshwater Bay House
Day 2: Freshwater Bay to Yarmouth via The Needles (22 miles)
The western wonders
Today’s route is shorter but packed with some of the island’s most spectacular scenery. The circular route takes you to The Needles before returning to the north coast:
- Alum Bay – Famous for its multi-colored sand cliffs
- The Needles – The island’s most iconic landmark (accessible via a short walk)
- Tennyson Down – Rolling chalk downland with sweeping sea views
- Totland Bay – A sheltered bay with clear waters
- Colwell Bay – Perfect for a refreshing swim in summer
This section includes some challenging climbs, particularly around Tennyson Down, but the descents are exhilarating.
Must-See: Take the chairlift down to Alum Bay beach to see the famous colored sands up close or visit The Needles Landmark Attraction for panoramic views.
Evening destination: Yarmouth
End your day in charming Yarmouth, with its well-preserved castle, bustling harbor, and excellent dining options. The town’s narrow streets are filled with independent shops and galleries.
Where to Stay: The George Hotel sits right on the waterfront, offering stylish rooms in a 17th-century townhouse. Their secure bike storage, maintenance area, and cyclist-friendly staff make this a perfect overnight stop.
Book your stay at The George Hotel
Day 3: Yarmouth to Ryde (23 miles)
The final stretch
Complete your island circumnavigation along the northern coast, through ancient woodlands and past Queen Victoria’s beloved island residence:
- Newtown National Nature Reserve – A peaceful estuary teeming with birdlife
- Cowes – The world-famous sailing center with vibrant waterfront
- East Cowes – Home to Osborne House, Queen Victoria’s holiday home
- Wootton Bridge – A picturesque village with a tranquil creek
- Quarr Abbey – A working Benedictine monastery with beautiful grounds
The terrain is generally gentler than previous days, making for a more relaxing final ride.
Cultural Stop: Osborne House offers fascinating insights into Victorian royal life and stunning gardens (secure bike parking available).
Return to Ryde
Complete your circumnavigation by returning to Ryde, where you can celebrate your achievement at one of the town’s excellent seafront restaurants before catching your return ferry.
Final Treat: The Garlic Pod & Farm Shop in Ryde offers the perfect post-ride refreshment with their famous garlic ice cream—more delicious than it sounds!
Planning your Isle of Wight adventure
When to go
The Isle of Wight enjoys more sunshine hours than most of the UK. May and September offer ideal conditions with warm temperatures, lower rainfall, and quieter roads.
Getting there
The island is easily accessible via:
- Wightlink ferries from Portsmouth to Fishbourne or Ryde, and Lymington to Yarmouth
- Red Funnel ferries from Southampton to East Cowes
- Hovertravel hovercraft from Southsea to Ryde (the fastest option)
All services accommodate bicycles (booking recommended).
Bike recommendations
A hybrid or touring bike is ideal for the mixed terrain. While predominantly on paved roads, some optional sections utilize gravel paths that connect to key attractions.
Navigation
The Round the Island route is well-signposted with blue-and-white signs, but using a GPS device provides additional reassurance. Download the official GPX files from Visit Isle of Wight’s cycling page.
Ready to circle the island?
This perfectly formed 70-mile adventure offers an ideal blend of challenging cycling, breathtaking scenery, and charming accommodations. Experience the best of British coastal cycling in one compact island package.
Book Your Isle of Wight Cycling Package
Our exclusive package includes ferry crossings, accommodation at handpicked cyclist-friendly hotels, luggage transfers, detailed route maps, and 24/7 support. Discover why the Isle of Wight is considered the perfect cycling destination with The Klub.
Have you cycled around the Isle of Wight? Share your favorite spots and tips in the comments below!
