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Isle of Wight - 5 days cycling
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Isle of Wight - 5 days cycling

Isle of Wight - 5 days cycling

Cycle the around the Isle of Wight

  • Cycling right the way around the Isle of Wight
  • Admire the sunny beaches and the beauty of the island
  • Discover Queen Victoria’s Osborne House
  • Marvel at the iconic Needles
  • Explore Newtown the old 'Rotten Borough' and Old Yarmouth Town
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Start & Finish: Ryde

Day 1: Arrive in Ryde
Day 2: Ryde to Yarmouth (39 km / 24,2 mi)
Day 3: Yarmouth to Chale (via the Needles) (38 km / 23,6 mi)
Day 4: Chale to Ryde (42 km / 26 mi)
Day 5: Arrangements end after breakfast

Day 1:    Arrive in Ryde

Ideally, take the train to Portsmouth and then the ferry or hovercraft over to the island. Ryde is a busy seaside town, take your time to explore and maybe try traditional fish 'n' chips on the promenade.

Accommodation: Ryde - we have selected a couple of 3-star hotels in the streets behind the esplanade. One is a quiet small hotel with a small bar, the other a popular town hotel with a big bar and restaurant.


Day 2:    Ryde to Yarmouth (39 km / 24,2 mi)

A great first day's ride takes you from the busy suburbs of Ryde and Cowes, to the beach resort of Gurnard and then through the pastoral elegance inland, winding through Newtown and some beautiful small villages before rolling into Yarmouth, a pretty, historic seaside town. On the way, the big attraction is Queen Victoria’s Osborne House. This is a big site, so you will need to watch your time if you visit. There is also Quarr Abbey, St. Mildreds Church Whippingham and Cowes. Newtown was the original capital of the island, it was attacked by the French in 1377 and never recovered. The old town hall dates back to the 1690's and is now in the care of the National Trust along with much of the surrounding land. Finally, we push into the old town of Yarmouth with its small pier and castle as well as an attractive square and church.

Accommodation: You will stay at a charming 16th century inn situated in the heart of Yarmouth's market square and only a stone's throw from the sea & harbour.

Day 3:    Yarmouth to Chale (via the Needles) (38 km / 23,6 mi)

A bike ride full of beauty with some hills, including an optional couple of steep hairpins up to the New Battery at The Needles Park. From there you can go no further, but it is a magnificent spot for views of the teeth-like stacks (The Needles) jutting out of the headland. It is not such a hard climb, and if you want to avoid cycling up, you could even walk or get the bus from the Alum Bay car park.

Follow on to Freshwater Bay, which has a couple of attractions including a thatched church. Then there is the (optional) chalky downland ride up and over the grassy downs called ‘The Tennyson Trail,’ this can also be bypassed if you don’t feel like it. The second half of the day is a bit easier with fast country roads, narrow winding lanes and pretty villages such as Brighstone, with some thatched cottages. Finally returning nearer to the coast, you arrive at the village of Chale underneath St. Catherine’s Down with its medieval lighthouse, the oratory tower. Chale Bay was at one time known as the Bay of Death; sixty ships were lost here between 1746 and 1808. Nearby are the Wealdon Beds which have yielded fossilised remains of dinosaurs.

Accommodation: Your inn in Chale is peacefully located.
Day 4:    Chale to Ryde (42 km / 26 mi)

The final day of cycling on the Isle of Wight is an interesting hilly mix of downs cycling and coastal stretches towards the end of the day. The route avoids the big tourist resorts of Ventnor, Shanklin and Sandown, opting for attractive hilly inland riding. This continues until you reach Bembridge where you pass around the estuarine harbour where there are a couple of venues to enjoy fresh crab or lobster. Then you are pedalling inland around pretty St. Helens with its harbour and attractive village green, before reaching the coastal road at Seaview. The last few kilometres are a relaxing roll into Ryde along the coast road, before climbing back into town to deliver your bike to the shop and return to your overnight accommodation.

Accommodation: We have selected for you a couple of 3-star hotels in the streets behind the esplanade. One is a quiet small hotel with a small bar, the other a popular town hotel with a big bar and restaurant.

Day 5:    Arrangements end after breakfast

After breakfast make your way to the pier to catch your return ferry to the mainland.


The hotels, inns, guesthouses and bed and breakfasts on this Isle of Wight cycling holiday are family-run, clean and comfortable (ranging from 2 to 4 stars), and provide access to local living thanks to your hosts. The hospitality is generous and their local knowledge is invaluable.

Where possible, we have chosen locations that add to your experience.

Dorset House (Ryde)
Dorset House (Ryde)

This has comfortable bedrooms offering a range of rooms. Mostly en-suite with TV and hospitality tray. Some with sea views across the Solent although we cannot guarantee this. Dorset House has a Residential License to help you wind down in the evening, but no restaurant here. A fine breakfast is served in the attractively appointed Dining Room to help you start the day. They also have a comfortable TV & Reading Lounge.


Harvey's B&B (Yarmouth)
Harvey's B&B (Yarmouth)

Harvey's is an elegant and historic Victorian style bed and breakfast built in the 18th century, situated in the main square in Yarmouth above a general store which used to be called ‘Harvey's’. It is well known for its hearty breakfast consisting of Isle of Wight free range pork produce, local milk and butter.

The Wight Mouse Inn (Chale)
The Wight Mouse Inn (Chale)

Popular pub with cosy rooms overlooking the downs. The restaurant does very reasonably priced pub food. This is also a good place to be if you like your beer.



This program can be booked any day between March 17th and October 20th, subject to availability and with the exception of 15-20 Jun & 30 Jul-06 Aug

The nearest international aiports to fly to/from are Bournemouth, Southampton and Gatwick (London)

Getting to/from the Isle of Wight (Ryde)

Nearest train station is in Portsmouth, from where frequent ferry & hovercraft services run.

Ferries run between Portsmouth - Fishbourne and Southampton - Cowes.

It is so easy (and cheap!) to go somewhere as different as the Isle of Wight. An hourly train from London Waterloo takes cyclists directly to Portsmouth Harbour (1.5-2 hours), where they can walk on to the passenger ferry. Less than half an hour later, the ferry arrives at Fishbourne. Then take the train into Ryde.

Those who can’t get there quickly enough can take the only scheduled passenger hovercraft service in the world, it takes just 10mins to get to the beach by the esplanade.


GPS tracks are available on request.



  • 4 nights´accommodation (B&Bs / Inns with ensuite facilities or private bathrooms where available)
  • 3 breakfasts
  • One piece of luggage per person transferred between your accommodation 3 times, not exceeding 20kg
  • Detailed route descriptions and OS maps
  • 24-hour telephone assistance

Not included

  • Dinner, lunch and drinks
  • Bike hire (please contact us for rental information)
  • Travel to the start and from the end point of the trip
  • Travel insurance
  • Admission fees
  • Personal expenses such as laundry and phone calls
  • Unscheduled transfers required during the trip


  • Single room supplement(s)
  • Solo traveller supplement
  • Bike rental

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