Isle of Wight Cycle

Isle of Wight Cycle

Trip Highlights

  • Cycling right the way around the island
  • The beaches and the beauty of the island
  • Queen Victoria’s Osborne House
  • The Needles
  • Newtown the old 'Rotten Borough' and Old Yarmouth Town

Trip Summary

This is a lovely short break for cyclists who want an attractive sightseeing tour, with a mixture of town and country. Almost half the island has been designated as an area of Outstanding Natural Beauty. Distances are fairly short giving you time to stop and explore. The route is undulating and there are a few hills but nothing particularly difficult. The holiday starts in the old seaside town of Ryde - the largest town on the island. Hire bikes are collected and the ride starts on mixed surfaces passing the interesting brick built Quarr Abbey and past Osborne House and Cowes, famous for its regattas. After the beaches of the north, the route tracks inland on fast roads through some attractive forest and farmlands and the estuary around Newport to the old town of Yarmouth. The route then cuts the busy western end of the island off by taking a cycle path following an old railway line to Freshwater Bay. You do have the option to take a diversion to ascend to the Needles Park for some splendid views. In good weather follow the Tennyson Trail to Brighstone and onto the ship wreck capital of the island - Chale. There is a final mix of hills around Bembridge Down, passing inland to visit attractive villages and a unique windmill and harbour before the last coastal stretch back into Ryde.


This trip involve cycling between 4-5 hours per day. You will need a good level of fitness and be in good health.


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 use a couple of 3 star standard hotels here 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.

Meals:  Nil

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 which 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 the attractive square and church. Accommodation: Yarmouth - The Bugle Inn is a charming 16th century inn situated in the heart of Yarmouths market square and only a stone's throw from the sea & harbour.

Meals:  B

A ride full of beauty with some hills, including an optional couple of steep hairpins up to the New Battery at The Needles Park from where you can go no further and for views of the teeth like stacks (The Needles) jutting out of the headland. It is not such a hard climb, and if you don’t want to cycle up, you could even walk or get the bus from the Alum Bay car park. Freshwater Bay then 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: Chale - The Wight Mouse Inn, is peacefully located.

Meals:  B

The final day 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 until you reach Bembridge where you pass around the estuarine harbour and there are a couple of venues for enjoying fresh crab, or lobster. Then you are pedaling inland around pretty St. Helens with its harbour and attractive village green, before reaching the coast 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.

Meals:  B

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

Meals:  B

What's Included

  • 4 breakfasts
  • 4 nights accommodation in B&Bs / Inns with ensuite facilities or private bathrooms where available
  • 3 luggage transfers
  • Information pack including notes and OS map (1 pack per room booked)
  • Emergency contact

What's Not Included

  • Lunches, dinners & beverages
  • Travel to and from Ryde
  • Bike Hire paid locally - approx £60
  • Transfers required during the cycle
  • Entrance Fees
  • Travel Insurance
  • Personal expenses such as laundry and phone calls

Upcoming Travel Dates


Enjoyed cycling along an old railway line, visiting churches and the views. The uphills really are not that bad. Overalll we had an excellent holiday.

G. French, United Kingdom, 26 Aug 2020

The Tuesday and the Thursday were excellent with good weather, lovely views while cycling and plenty of interesting places to visit. The Wednesday was very wet indeed and blowing a gale. After leaving Yarmouth, the first stop was Alum Bay and the Needles.Two visits to both the Alum Bay restaurant and the Glass Factory dried us out and warmed us up enough to set-out on the second half of the journey. By the time that we arrived at the accommodation in Chale, the wind had dropped and the sun had come out. We travelled in the 2020 summer.

P. Luard, Godalming, UK, 17 Sep 2020


Duration:5 Days
Starting Point:Ryde
Finishing Point:Ryde
Activities:Self-Guided Cycling
Grade:introductory to moderate  Click for more information
Trip Code:WIC
Prices From:GBP£585 Per Person
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.