🔒 Europe Price Lock 🔒Save on France, Italy, Spain & Portugal 2025Book now
5 days
  • self guided cycle
  • 4 nights in hotels and guesthouses
  • 3 Breakfasts





Trip Code: WIC

Isle of Wight Cycle 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.

Trip Grading

introductory to moderate

More info about grading system

Traveller Rating


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 Wight House is situated at the higher end of town, close to the bike hire shop and with plenty of options to go for a meal around.

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. 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: The Bugle Coaching Inn (room only) is a charming 16th century inn situated in the heart of Yarmouth's market square and only a stone's throw from the sea & harbour. Bike storage is through the back. Tea & coffee making facilities in the rooms, which are all en-suite.

Meals:  Nil

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.

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. 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.

Meals:  B

After breakfast make your 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 on a twin share basis with ensuite facilities or private bathrooms where available (1 night in an inn on a room only basis)
  • One piece of luggage per person transferred from Inn to Inn, not exceeding 15kg
  • 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 involves cycling between 4-5 hours per day. You will need a good level of fitness and be in good health. *Please note that by UK law, you can ride an electric bike if you’re 14 or over.

Departure dates

Daily from 15 Mar to 20 Oct (except 17 - 23 Jun & 23 Jul - 2 Aug)


High Season
Blackout Periods: Isle of Wight Festival from 17-23 Jun & Cowes Week from 23 Jul - 2 Aug.
By UK law, you can ride an electric bike if you're 14 or over.
Minor changes may apply to 2025 itinerary.

Want to organise a private group?

Fundraising events, sporting groups, family treats; learn how you can organise a Private Group from just 6 travellers.

Priceper person from


Options & Supplements*
  • e-Bike SupplementUSD$140
  • Single Supplement 2025USD$240
  • Solo Traveller Supplement 2024USD$320
  • Solo Traveller Supplement 2025USD$350
*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 is the world's only year-round passenger hovercraft service and makes for a fantastic experience.

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 to get a full experience of the island. 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!

Bike hire is included on this trip and helmets are also provided if wanted. 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. 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.

Although the bikes come with lighting and even if you do not intend to cycle during the evenings, we recommend bringing some simple led lights with you. 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.

Isle of Wight Cycle Trip reviews

Why travel with us

Making Europe Affordable

We offer different levels of accommodation and comfort so that even the most budget conscious can treat themselves to active holidays on Europe's most celebrated tracks and trails. Our trips are great value for money because you only pay for what you want.  

Self-Guided Specialists

Our wide range of self-guided itineraries embody the UTracks philosophy of exploring Europe your way. We handle the logistics so all that's left for you to do is enjoy exploring Europe at your own pace. Most depart daily with a minimum of two people, meaning maximum flexibility.

Our Wide Range

With close to 400 trips in almost 50 countries, including the largest range of bike & boat holidays in Europe, we're confident that we can organise an Alps walk, Camino de Santiago or Via Francigena experience, Food Lovers' trip or a tour in a lesser-known pocket of Europe that you will love. 

Join Newsletter
<img src='/portals/World%20Expeditions/Icons/brands/small/ADS.jpg' class='brandPopoverIcon' alt="Adventures South"> <div class='brandPopoverBrandName'>Adventure South</div>
Adventure South NZ is unrivalled in their geographic coverage, originality and overall quality of adventures holidays in New Zealand. Choose from walking, cycling, winter or multi-activity holidays, on either the North or South Island.
<img src='/portals/World%20Expeditions/Icons/brands/small/AWH.jpg' class='brandPopoverIcon' alt="Australian Walking Holidays"> <div class='brandPopoverBrandName'>Australian Walking Holidays</div>
Australian Walking Holidays specialises in small group guided walking adventures. Since 1982 we have been guiding small groups of travellers on Australia's finest walks across our tropical, coastal or red centre landscapes.
<img src='/portals/World%20Expeditions/Icons/brands/small/GCT.jpg' class='brandPopoverIcon' alt="Great Canadian Trails"> <div class='brandPopoverBrandName'>Great Canadian Trails</div>
Great Canadian Trails specialises in active holidays in Canada. With both guided and supported self-guided options available, our unique itineraries draw upon some of Canada's most inspiring parks, trails and landscapes from coast to coast.
<img src='/portals/World%20Expeditions/Icons/brands/small/HUM.jpg' class='brandPopoverIcon' alt="Humac Challenge"> <div class='brandPopoverBrandName'>Huma Charity Challenge</div>
Huma enables those with adventurous spirits to challenge themselves and make a difference for a cause close to their heart. Travel, fundraise and meet life-long friends on one of Huma's meaningful and unique challenges around the world.
<img src='/portals/World%20Expeditions/Icons/brands/small/WB.jpg?v2' class='brandPopoverIcon' alt="Walkers’ Britain"> <div class='brandPopoverBrandName'>Walkers' Britain</div>
Walkers' Britain (formerly Sherpa Expeditions) have specialised in walking and cycling trips in the United Kingdom and Europe since 1973. Explore iconic trails and destinations on a self guided or small group active holiday with Walkers' Britain.
<img src='/portals/World%20Expeditions/Icons/brands/small/WB.jpg?v2' class='brandPopoverIcon' alt="Walkers’ Britain"> <div class='brandPopoverBrandName'>Walkers' Britain</div>
Walkers' Britain (formerly Sherpa Expeditions) have specialised in walking and cycling trips in the United Kingdom and Europe since 1973. Explore iconic trails and destinations on a self guided or small group active holiday with Walkers' Britain.
<img src='/portals/World%20Expeditions/Icons/brands/small/TAS.jpg' class='brandPopoverIcon' alt="Tasmania Expeditions"> <div class='brandPopoverBrandName'>Tasmanian Expeditions</div>
Tasmanian Expeditions is the most experienced operator of treks and adventure travel holidays in Tasmania. We own and operate the most comprehensive range of adventure holidays available across Tasmania's varied landscapes.
<img src='/portals/World%20Expeditions/Icons/brands/small/UTX-new.jpg' class='brandPopoverIcon' alt="Utracks"> <div class='brandPopoverBrandName'>UTracks</div>
UTracks are the active European holiday specialists. Whether you prefer cycling or walking, 2-star or 4-star, small groups or self guided, land, river or sea – UTracks can help you to explore Europe exactly the way you want.
<img src='/portals/World%20Expeditions/Icons/brands/small/WYA.jpg' class='brandPopoverIcon' alt="World Expeditions Schools"> <div class='brandPopoverBrandName'>World Expeditions Schools</div>
World Expeditions Schools is our specialist division dedicated to organising tailor made overseas school group adventures. Specialists in Service Learning projects, choose from more destinations than any other school group provider.
<img src='/portals/World%20Expeditions/Icons/brands/small/YOM.jpg' class='brandPopoverIcon' alt="Yomads"> <div class='brandPopoverBrandName'>Yomads</div>
Yomads offers adventures for the 20s and 30s on six continents. Designed as a way to bring young and likeminded travellers together, Yomads caters to those interested in lightly structured and active trips that allow freedom to roam and explore.
<img src='/portals/World%20Expeditions/Icons/brands/small/ACT.jpg' class='brandPopoverIcon' alt="Australian Cycle Tours"> <div class='brandPopoverBrandName'>Australian Cycle Tours</div>
Australian Cycle Tours specialises in high quality self guided and guided cycling experiences in a selection of the most beautiful regions in Australia.
<img src='/portals/World%20Expeditions/Icons/brands/small/WEX.jpg' class='brandPopoverIcon' alt="World Expeditions"> <div class='brandPopoverBrandName'>World Expeditions</div>
The pioneers of original, worldwide adventure travel holidays since 1975
<img src='/portals/World%20Expeditions/Icons/brands/small/TJX.jpg' class='brandPopoverIcon' alt="Trail Journeys"> <div class='brandPopoverBrandName'>Trail Journeys</div>
Self-guided cycling experts on New Zealand's Otago Rail Trail and more
<img src='/portals/World%20Expeditions/Icons/brands/small/BMAC.jpg' class='brandPopoverIcon' alt="Blue Mountains Adventure Company"> <div class='brandPopoverBrandName'>Blue Mountains Adventure Company</div>
The original Blue Mountains canyoning, hiking, climbing and abseiling experts
<img src='/portals/World%20Expeditions/Icons/brands/small/GWNZ.jpg' class='brandPopoverIcon' alt="Great Walks of New Zealand"> <div class='brandPopoverBrandName'>Great Walks of New Zealand</div>
Explore New Zealand's most spectacular wilderness regions with the self-guided hiking experts
<img src='/portals/World%20Expeditions/Icons/brands/small/NAA.jpg' class='brandPopoverIcon' alt="North America Active"> <div class='brandPopoverBrandName'>North America Active</div>
USA Canada hiking & cycling tour specialists, choose from self-guided or guided trips