Self-guided Isle of Wight cycling holiday. Fully supported, GPX files, bag moves, quality hotels & more. In 5 days, circumnavigate this picturesque British island.
At a glance
Duration
5 days
Route
→
Countries
United Kingdom
Activity level
moderate
Style
Beach & Islands, Cycling
Group size
Ask
Flights
Not included
Solo travellers
Ask an agent
Day by day
Your journey through
United Kingdom
Day 1Day 1: Arrive RydeIdeally, take the train to Portsmouth and then the ferry or hovercraft (world's last year-round passenger service hovercraft!) over to the island. Ryde is a typical seaside town, take your time to explore and maybe try traditional fish 'n' chips on the promenade. Accommodation: The Dorset Hotel is situated close to restaurants, cafes and pubs and easy access to the beach and bike rental shop NB: You can collect your bike Mon-Wed & Fri: 9am - 12pm and 1pm - 6pm. Saturday collections are between 9am and 12 midday only. If starting your trip on a Wednesday or Saturday, please note you will have to pick up your bike on your arrival day, there is an extra charge for this (see below). You can return your bike any day of the week. Please take into account shop opening times for your bike collection.
Ideally, take the train to Portsmouth and then the ferry or hovercraft (world's last year-round passenger service hovercraft!) over to the island. Ryde is a typical seaside town, take your time to explore and maybe try traditional fish 'n' chips on the promenade. Accommodation: The Dorset Hotel is situated close to restaurants, cafes and pubs and easy access to the beach and bike rental shop NB: You can collect your bike Mon-Wed & Fri: 9am - 12pm and 1pm - 6pm. Saturday collections are between 9am and 12 midday only. If starting your trip on a Wednesday or Saturday, please note you will have to pick up your bike on your arrival day, there is an extra charge for this (see below). You can return your bike any day of the week. Please take into account shop opening times for your bike collection.
Day 2Day 2: Ryde to Yarmouth 39km / 24.25 milesA 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. Mildred's Church in Whippingham, and Cowes. Newtown was the original capital of the island, which was attacked by the French in 1377 and never recovered. The old townhall dates back to the 1690's and is now in the care of the National Trust along with much of the surrounding land. Finally, you push into the old town of Yarmouth with its small pier and castle as well as the attractive square, independent shops, cafes and church. Accommodation: tonight's accommodation is at Bugle Inn, a historic 16th-century establishment located in the heart of Yarmouth's market square on the Isle of Wight.
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. Mildred's Church in Whippingham, and Cowes. Newtown was the original capital of the island, which was attacked by the French in 1377 and never recovered. The old townhall dates back to the 1690's and is now in the care of the National Trust along with much of the surrounding land. Finally, you push into the old town of Yarmouth with its small pier and castle as well as the attractive square, independent shops, cafes and church. Accommodation: tonight's accommodation is at Bugle Inn, a historic 16th-century establishment located in the heart of Yarmouth's market square on the Isle of Wight.
Day 3Day 3: Yarmouth to Chale (via The Needles) 38 km / 23.6 milesA cycle ride full of beauty with some hills, including an optional couple of steep hairpins up to the New Battery at The Needles Park. From here you can go no further and have great 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: The Wight Mouse Inn is peacefully located with impressive views over the white cliffs from its big pub garden, explaining why this is such a popular place with locals and visitors alike. Rooms are spacious and en-suite with tea & coffee making facilities.
A cycle ride full of beauty with some hills, including an optional couple of steep hairpins up to the New Battery at The Needles Park. From here you can go no further and have great 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: The Wight Mouse Inn is peacefully located with impressive views over the white cliffs from its big pub garden, explaining why this is such a popular place with locals and visitors alike. Rooms are spacious and en-suite with tea & coffee making facilities.
Day 4Day 4: Chale to Ryde 42km / 26 milesThe 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. Here you pass around the estuarine harbour and there are a couple of venues for enjoying fresh crab or lobster. Then you are pedalling 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 coastal road, before climbing back into town to deliver your bike to the shop and return to your overnight accommodation.
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. Here you pass around the estuarine harbour and there are a couple of venues for enjoying fresh crab or lobster. Then you are pedalling 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 coastal road, before climbing back into town to deliver your bike to the shop and return to your overnight accommodation.
Day 5Day 5: End of tourAfter breakfast make your way to the pier to catch your return ferry to the mainland.
After breakfast make your way to the pier to catch your return ferry to the mainland.