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introductory to moderate

Traveller Rating


  • self guided cycle
  • 4 nights in hotels and guesthouses
  • 3 Breakfasts

5 Days£630GBP


Trip Code: WIC

Trip highlights

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

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.



Starting Point:


Finishing Point:


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 - Dorset House is situated close to the sandy beaches and esplanade.

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:  Nil

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



The map and elevation chart are for illustrative purposes only and meant to provide general guidelines.
On self guided trips, actual route information provided before departure will be more detailed.


  • 3 breakfasts
  • 4 nights accommodation in B&Bs / Inns with ensuite facilities or private bathrooms where available (1 night in an inn on a room only basis)
  • 3 luggage transfers (15kg is the total maximum limit)
  • Information pack including notes and OS map (1 pack per room booked)
  • 24/7 Emergency contact
  • Bike Hire for 3 days: Hybrid bike incl. puncture repair kit. E-Bike Hire on request (supplement applies, please ask us for details)

  • Bike helmet & panniers
  • Lunches, dinners & beverages
  • Travel to and from Ryde
  • Transfers required during the cycle
  • Entrance Fees
  • Travel Insurance
  • Personal expenses such as laundry and phone calls
  • 1 breakfast in Yarmouth
  • Guide - this is a self guided holiday
  • A supplement will apply if you are travelling solo or book a single room


Bike information


introductory to moderate


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

Departure dates

Daily from 1 Apr to 22 Oct (except 15 - 20 Jun & 28 Jul - 05 Aug)


Blackout Periods: Isle of Wight Festival from 17-23 Jun & Cowes Week from 23 Jul - 2 Aug.
Please note that minor changes to your 2024 itinerary may apply.

Priceper person from


Options & Supplements*
  • e-Bike SupplementGBP£100
  • Single SupplementGBP£190
  • Solo Traveller SupplementGBP£230
*Prices listed are per person

Frequently Asked Questions

If you are a foot passenger travelling to Ryde from Portsmouth and/or if you have travelled by train to Portsmouth harbour, then this feeds directly onto the Isle of Wight ferry. Please note though that once you've arrived in Ryde, you have quite a long walk with your bag off the pier. Alternatively, you can take the hovercraft via a connecting bus from Portsmouth and Southsea station. This unusual form of travel takes you directly to the beach in Ryde and where your first hotel is located.

This cycling holiday on the Isle of Wight doesn't completely stick to the coast. We have designed the cycle route in such a way that you will stay on quieter routes around the island and at times you will cycle inland quite a way. This includes sections passing private estates such as Osbourne House - where you will have time to visit.

The Isle of Wight is of course modern, but in many ways the infrastructure dates back and a lot of the set-up is from another era. This gives the feeling that the British isle has a slower, quieter pace of life than on the mainland UK. There is always also the island mentality!

While bike hire is included on this trip, helmets are not. We would recommend for reasons of preferential size and hygiene that you bring your own. Wearing a helmet is not a legal requirement in the UK but more people are wearing them. Also, if you are not wearing a helmet and have an accident, your insurance company may tend to take a dim view as they may try to get out of paying for accidents, however they may have been caused.

Basic stuff for changing tyres etc. is included with your hire bike, but it could be worth bringing with you a reasonable bike multi tool that you know.

It will also be worth bringing some simple led lights with you, or buy them in the shop. Even if you do not intend to cycle during the evenings, low fogs during the day are quite common at any time of the year and you may want to cycle to/from the hotel and a restaurant in the evening.

Yes it is possible to upgrade your standard bicycle hire to an electric bike on this cycling holiday on the Isle of Wight. The fee for this is mentioned in the Departure Dates section on this page. Please request this with us as early as possible as there is a limited supply of e-bikes.

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