Cycle around the beautiful Isle of Wight in South England
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.
Highlights of the Isle of Wight Cycling Tour
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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
Distance: None
Meals: None
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
Distance: 39km
Meals: Breakfast
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
Distance: 38km
Meals: Breakfast
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
Distance: 42km
Meals: Breakfast
Day 5 Depart
Today is the final day of your time in Isle of Wight, when you departure after your breakfast.
Overnight Location: None
Distance: None
Meals: Breakfast
This self-guided tour is always run as a private tour for your group only.
2024 Departures
The departures are available daily, from March 15th to October 20th. All the prices below are per person.
- Solo traveller: $875 USD
- Single room (travelling with group): $825 USD
- Sharing a double room: $575 USD
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.
Hotels on Standard Tour
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.
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.
What’s Included in the Isle of Wight Cycling Tour?
Meals
4 breakfasts are included.
Accommodations
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
Frequently Asked Questions about Isle of Wight Cycling Tour
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