Isle of Wight Cycling Tour

Isle of Wight Cycling Tour

Isle of Wight Cycling Tour


From $625USD




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Cycle around the beautiful Isle of Wight in South England

Visit the famous Queen Victoria’s Osborne House

Observe the beautiful Needles of Isle of Wight from your biking path

Enjoy the biking around the Isle on your own pace

Visit Old Yarmouth Town and Newtown - the old 'Rotten Borough'

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 shipwreck 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.

Isle of Wight Cycling Tour Itinerary

Day 1 Arrival 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.

Overnight Location
Hotel/BB in Ryde

Day 2 Ryde to Yarmouth

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.

Overnight Location
Hotel/BB in Yarmouth

Day 3 Yarmouth to Chale (via the Needles)

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.

Overnight Location
Hotel/BB in Chale

Day 4 Chale to Ryde

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.

Overnight Location
Hotel/BB in Ryde

Day 5 Depart

Today is the final day of your time in Isle of Wight, when you departure after your breakfast.

Overnight Location

Isle of Wight Cycling Tour Price and Dates

This self-guided tour in Isle of Wight is always run as a private tour for your group only and the price per person depends on the type of the room that you choose.

The price below is per person:

  • Price per person staying in a single room: $825USD per person
  • Price per person sharing a double room: $625USD per person
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Accommodation on Isle of Wight Cycling Tour

There is a variety of accommodation along the route ranging from bed and breakfasts, lodges, pubs and small hotels. They are run by cycling-friendly hosts offering en-suite or private facility rooms with a tasty breakfast to get you ready for the day ahead. Further facilities such as washing and drying facilities, packed lunches and packed lunches are available in some accommodations, you will be advised on your listing of what is available.

In some cases, the accommodation listed below may need to be substituted for other comparable accommodations.

Single Rooms and Solo Travellers
Rooms are double occupancy. You can pay a supplement to have a private room in a hotel where possible. Solo travellers may be required to pay a supplement.

Night 1

Hotel/BB in Ryde

There are a few options for your stay in Ryde, with two options being our favorite: One is a quiet small hotel with a small bar, the other is a popular town hotel with a big bar and restaurant.

The Bugle Inn in 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.

The Wight Mouse Inn in Chale

This family-run hotel is a tranquil and clean establishment with a close proximity to the beach.

Night 4

Hotel/BB in Ryde

There are a few options for your stay in Ryde, with two options being our favorite: One is a quiet small hotel with a small bar, the other is a popular town hotel with a big bar and restaurant.

Hotels on Standard Tour

What’s Included in the Isle of Wight Cycling Tour?


4 breakfasts are included.


Accommodations for 4 nights are included.

Transportation during the Tour

This tour includes luggage transfers for your luggage; however, you are in charge of any personal transfers needed.

Also Included

  • Detailed documents, guides, route maps, and GPX tracks
  • Emergency telephone support hotline for the duration of the tour
  • Pre-planned route

Not included

  • Getting to or from Ryde
  • Travel insurance
  • Visas if required
  • Meals, drinks, or snacks not previously mentioned
  • Guide services
  • Tourist hotel tax, payable each night at hotel
  • Airport transfers
  • Gratuities for drivers, servers, or other staff if desired
  • Bike rental

Optional Extras

  • Bike rental
  • Single occupancy upgrades

Frequenty Asked Questions about Isle of Wight Cycling Tour

How hard is the Isle of Wight Cycling Tour?

We rate this tour as a 2 / 5. The cycling is mainly along quiet country roads.

I’ve never been on a self-guided trip! How does it work?

Self-guided travelling is not difficult! For many, it is a preferred type of travel since you are in charge of your own time and pace. You are provided with all the information you’ll need to follow the route each day and often have access to phone support or other kinds of assistance. However, self-guided travelling requires good navigation skills and those who don’t feel confident in unknown places should consider booking guided tours.

Do I need a visa to travel to England?

Check with your local country about visa requirements. You could also try this website, though you should verify with your government.

Are meals included on the Isle of Wight Cycling Tour?

4 breakfasts are included.

Do I need insurance?

Yes, it is mandatory to have health and medical insurance to join this trip, and your insurance should cover cycling. Get your travel insurance.

How do I get to Ryde to start this tour?

You can get to Ryde via ferry or Hovercraft from Portsmouth. Portsmouth has direct train connection to London. You can also fly to Southampton Airport and then transfer by bus and train to Portsmouth. If driving, you can take a csr ferry from Portsmouth to Cowes or from Lynmouth to Yarmouth. There are also ferries to Isle of Wight from Lymington.

Where does the Isle of Wight Cycling Tour end?

This tour ends where it starts, in Ryde.

Can I rent a bike?

Yes, you can rent a bike during the booking process.

Can I bring my own bike?

Yes. If you bring your own bike, it should be a road bike suitable for the demands of the tour. If you are bringing your own bike, make sure to include it in any public transport tickets you reserve.

Do I need special vaccines to travel to Scotland?

Check with your family doctor.

Are there any travel restrictions for England?

Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.


All tours on 10Adventures are operated by highly vetted local tour operators and guides.

Having local tour operators and guides means you get a more authentic experience, and your booking creates jobs in the local communities you visit.

Details of the local tour operator will be listed on your booking invoice. If you have questions about the local operator prior to booking, please click the “Ask a Question” button below.

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From $625USD




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Tour Difficulty

We rate this tour as a 2 / 5. The cycling is mainly along quiet country roads.

Read about our scale for Tour Difficulty Ratings.

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