A five day holiday cycling in the Isle of Wight, following its 55km spectacular circuit around its cliffs, chalky downs and coves – a perfect pocket of English landscapes. The Isle of Wight is just over two hours from London and easily accessible by train and ferry, from a number of different ports. Staying in locally owned B&Bs and guesthouses, with your luggage transferred for you, enjoy a mellow five days of cycling, either on traditional or e-bikes, across the grass and chalky downs, traditional seaside towns of Yarmouth and Ryde, as well as ancient villages of Chale and St. Helens. Bring your own bike or we will organise a rental for you, with e-bikes also available.
- Cycling all around the Isle of Wight
- Enjoy the Isle of Wight’s beaches
- Queen Victoria’s Osborne House
- The Needles
- Explore Newtown, the old ‘Rotten Borough’ and Old Yarmouth Town
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Day 1: Arrive Ryde
With long, spacious stretches of sandy beach, local shops and great restaurants, Ryde is a quirky mix of a traditional seaside fun, Victorian architecture and unexpected hidden gems.
- Accommodation: Dorset House or similar
Day 2: Ryde to Yarmouth | 39km
A great first day’s ride takes you from the relatively busy towns of Ryde and Cowes, to the beach resort of Gurnard and then through pastoral perfection 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 substantial but wonderful attraction, so you will need to watch your time if you visit. There is also Quarr Abbey, St. Mildred’s Church, Whippingham and Cowes to enjoy en route. Newtown was the original capital of the island and the old town hall dates back to the 1690s and is now in the care of the National Trust along with much of the surrounding land. At the end of the day, you cycle into the old town of Yarmouth with its small pier and castle as well as an attractive square and church.
- Cycling for the day: 39km
- Accommodation: Harvey’s B&B or similar
Day 3: Yarmouth to Chale | 38km
A bike ride full of beauty with a few hills, including an optional couple of steep hairpins up to the New Battery at The Needles but definitely worth the climb, as this is one of the most superb views on the island. It is not such a hard climb but, if you want to avoid cycling up, you can walk or get the bus from the Alum Bay car park.
Follow on to Freshwater Bay, which 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, where you are rewarded with magnificent views. The second half of the day is a bit easier with fast country roads, narrow winding lanes and pretty villages such as Brighstone. Finally, returning nearer to the coast, you arrive at the village of Chale underneath St. Catherine’s Down with its medieval lighthouse. 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.
- Cycling for the day: 38km
- Accommodation: The Wight Mouse Inn or similar
Day 4: Chale to Ryde | 42km
This final day of cycling on the Isle of Wight is an interesting hilly mix of cycling on the downs with some 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. This continues until you reach Bembridge where you cycle around the estuarine harbour where there are a couple of great spots to enjoy fresh crab or lobster. Then you are pedalling inland around pretty St. Helens with its harbour and attractive village green, before reaching the coastal 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.
- Cycling for the day: 42km
- Accommodation: Dorset House or similar
Day 5: Departure
Departure or extra nights upon request.
What to expect
Accommodation on this tour includes a mix of small, locally-owned hotels, B&Bs and traditional guesthouses. They have been carefully selected based on a variety of criteria including their location, warm hospitality, fine local food or commitment to responsible tourism. All rooms have en-suite or private bathrooms.
Click to view default hotels
Hotels are subject to availability. In the event of a particular hotel being fully booked for your chosen dates, we will replace it with a hotel of equal value and quality level. We will provide exact accommodation details to you upon booking confirmation.
Breakfast is included on all days. When no restaurant location is available on the route, lunches and snacks should either be bought from local shops, or packed lunches can be pre-ordered from your hotel the night before. You can have dinner at the guesthouse you are staying at or at the village pubs and restaurants.
Difficulty and terrain
Expect some long steep hills, which all fit cyclists should be able to complete, especially as the cycling days do not exceed, on average, 40km with a total ascent/descent of 915m (read more about difficulty grades). A comprehensive guidebook and map are supplied. You can also call our 24/7 local assistance phone number anytime. More detailed info on route navigation will be included in your holiday information pack.
When to go
This trip is available from March until October.
The flexibility of self-guided holidays means that there are no fixed dates, and you can start your trip on any date during the season. If you are a seasoned and well-equipped cycler, we can eventually book you on off-season dates.
Click to view travel options
Our recommended airports for this tour are Bournemouth, Southampton and Gatwick (London).
By train or bus
- The nearest train station is in Portsmouth, from where frequent ferry & hovercraft services run.
- Ferries run between Portsmouth – Fishbourne or Ryde, Southampton – Cowes, Lymington – Fishbourne. For more information, use the Omio planner above.
- An hourly train from London Waterloo takes you directly to Portsmouth Harbour (1.5-2h), where you can walk on to the passenger ferry. Less than half an hour later, the ferry arrives at Fishbourne. Then take the train into Ryde. You can also take the train to Southampton or Lymington.
- Those who can’t get there quickly enough can take the only scheduled passenger hovercraft service in the world; it takes just 10mins to get to the beach by the esplanade.
- 4 nights in twin/double rooms (small hotels, B&Bs and guesthouses)
- 4 breakfasts
- Detailed journey documentation and practical information: route notes and GPX tracks
- Luggage transfers from hotel to hotel – One piece up to 20kg per bag
- 24/7 phone assistance by our local office/representative
- Airfare and connecting land transfers
- Lunches, dinners, drinks and snacks
- Travel insurance (required – get a quote online)
- Personal expenses
- Local tourist taxes and entry fees (payable on-site)
- Any items not explicitly listed as included
Options, extras and supplements
- If you’re travelling in a group, a supplement applies to group members who would like to have a room of their own.
- A supplement applies to members of a group who require a single room
- This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
- Bike/e-bike rental
- Extra nights along the trail are bookable upon request
- Hybrid bike – 24 gears women’s or men’s lightweight day bikes, perfect for exploring the area.
- E-bike – comfort e-bike that exudes elegance, has sufficient power, is easy to operate and at the same time ensures a relaxed riding experience.