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Isle of Wight Bike Tour

Explore the Isle of Wight on two wheels, discovering coastal roads, historic villages, Osborne House, The Needles, and stunning seaside views on a scenic adventure.

Starting point

Ryde

Finish point

Ryde

Duration

5 days / 4 nights

Season

From April to October

Fitness level

2/5

Tour type

Gravel / E-bike

Number of people

2

Choose your style

Secure your spot with no risk - free cancellation in the next 48 hours
  • Ride through the Isle of Wight’s scenic coastal roads and rolling countryside
  • Climb to The Needles for breathtaking views over the iconic chalk stacks
  • Ride the stunning Military Road with uninterrupted sea views on your right
  • Explore historic Osborne House, Queen Victoria’s seaside retreat
  • Visit charming villages like Godshill, Yarmouth, and Bembridge Windmill
  • End your journey in Ryde, cycling along its Victorian promenade by the sea

What’s included in the price?

Self-guided

4 nights in 3-star hotels with breakfast
Digital guidebook with detailed itinerary and route instructions
GPS navigation with an easy-to-use app
Tour design and organization
Service and support during your tour
Luggage transfer

Not included

Tourist tax

Optional extras

Airport transfer
E-bike
Gravel bike
Hotel upgrades
Single supplement

Discover the Isle of Wight on a self-guided cycling journey, combining stunning coastal views, historic landmarks, and charming villages

From dramatic chalk cliffs to rolling countryside, each mile offers a new experience, whether it's exploring Osborne House, riding past medieval churches, or enjoying local seafood in harbor towns like Yarmouth.

Along the route, you’ll visit some of the island’s most iconic sights. Marvel at The Needles, a series of striking chalk stacks rising from the sea, and ride along the breathtaking Military Road, offering uninterrupted coastal views. 

Pass through historic Newtown, once the island’s capital, and stop at Bembridge Windmill, the last surviving windmill on the Isle of Wight. You will wander the charming streets of Ventnor, explore the golden beaches of Sandown and Shanklin, and soak in the seaside charm of Ryde with its historic pier and panoramic Solent views.

This route is perfect for cyclists seeking a moderately challenging yet rewarding ride.

We take care of all the logistics so you can focus on the ride. From booking comfortable accommodations to providing GPS navigation, a detailed digital guidebook, and luggage transfers, we ensure a seamless experience. 

Our team is on hand to offer local recommendations and support, making your cycling adventure stress-free and enjoyable.

Whether solo or with friends, this tour offers freedom, flexibility, and a deep connection to the island’s breathtaking landscapes and rich history.

Map

Frequently Asked Questions

Self-guided cycling tours provide a flexible and independent way to explore the UK on two wheels. You can set your own pace, modify your schedule, and immerse yourself in the journey. Our team handles all logistics, including booking accommodations, providing detailed itineraries, GPS routes, and 24/7 support. This ensures a stress-free experience while giving you the freedom to discover the UK's scenic landscapes and cultural landmarks at your leisure.

To help you choose the most suitable tour, we rate difficulty on a scale of 1 to 5:

  • 1/5 – Easy: Daily rides of about 30 km on mostly flat terrain. Ideal for beginners or those with little cycling experience.
  • 2/5 – Moderate: Up to 40 km per day with slight elevation gains (up to 200 m). Suitable for anyone in reasonable health.
  • 3/5 – Intermediate: Covering around 50 km daily, with elevation gains of up to 500 m. On flatter days, distances may be longer. Best for recreational cyclists with a good fitness level.
  • 4/5 – Advanced: Expect daily rides of 60 km or more, with climbs exceeding 500 m. Some stages may include up to 1000 m of elevation. Designed for experienced cyclists accustomed to hills.
  • 5/5 – Challenging: Long distances with steep climbs, perfect for highly experienced cyclists seeking a demanding yet rewarding challenge.

Accommodation availability varies based on the season, so we partner with a selection of trusted lodging providers that meet our quality standards. We aim to match accommodations to your preferences and budget, ensuring a comfortable stay. While our itineraries provide examples of accommodation types, specific locations may change depending on availability.

We offer tours for various cycling styles, including road cycling, gravel riding, and mountain biking. Our specialists can recommend the best option based on your experience, terrain preferences, and group needs. 

Gravel bikes are the most versatile choice, even for road cycling routes, as they allow for smooth riding on paved roads and scenic backroads that may be less maintained. These bikes also provide extra comfort for long-distance rides.

Since many of our tours feature hilly landscapes, some cyclists opt for e-bikes for added support. However, we recommend having prior experience with e-bikes, as they handle differently from traditional bicycles.

If bringing your bike isn’t an option, we offer rental services. Our range includes road bikes, gravel bikes, mountain bikes, and e-bikes to match the needs of your tour. Simply provide your preferred bike size and any special requests, and we’ll ensure you get the best fit for a comfortable ride.

Bike rentals include delivery before the tour and collection afterward. Each rental comes with a helmet, spare chain, basic repair kit, and pedals if required.

We strive to accommodate dietary needs, though availability varies by region. Vegetarian meals are usually easy to find in larger towns and cities, but vegan options may be more limited in rural areas. Many of our lunch stops are at traditional UK eateries, where dietary choices might be restricted, so we recommend planning.

The best time to cycle in the UK is from late spring to early autumn (May to September). May and June offer long daylight hours and relatively dry conditions, while September provides quieter routes with fewer tourists. However, UK weather is unpredictable, so it’s always wise to be prepared for occasional rain.

Most tours can continue in light rain with the right clothing. Thunderstorms are more common in summer afternoons, so we suggest starting your rides early in the day. If extreme weather is forecasted, we can modify your itinerary. Our support team is available to help with last-minute adjustments.

Ratings & Reviews

Google Reviews

5.0 average rating

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Top Rated Brand
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Angie Osborne

Verifed customer · 6 months ago

This tour met and exceeded our expectations. It was certainly challenging cycling for seniors but most of us did it all seven days. Scenery and culture of the islands was glorious. Guide and crew was superb!

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Greg Martin

Verifed customer · 7 months ago

Great holiday. Really easy to follow routes, good choice of hotels and the en route places to eat and visit was really helpful. Super responsive to questions during my holiday. Would definitely use them again.

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Chris Pyne

Verifed customer · 1 year ago

First class company with a well planned route, great accommodation and simply outstanding support in time of trouble. We did a two week ride from Bled to Pula in September 2023. Fair to say we hit a lot of problems courtesy of BA with rescheduled and diverted flights, lost bags, problems with our own bikes, returning rental bikes and more. Daja was simply amazing in helping us sort all of them out and was so accessible at all hours. She even managed to source and buy a forgotten Thru-axle and deliver it personally to our hotel, which is far and above any service i would reasonably expect. Thank you !! Our accommodation was fantastic and far better than expected in all but one location. The route planning in Slovenia was great but due to our decision to bring road bikes from the UK and the nature of the roads in Croatia, our second week was a bit tricky route wise and it would have been good to have had a discussion about this section beforehand. A Gravel bike is far better suited to Croatia although this was our decision to bring road bikes. Transport arrangement and logistics were flawless. Overall, i would change very little and we will definitely be returning to Slovenia. Daja was fantastic and I absolutely recommend Slovenia Cycling Holidays and will be using their services again.

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Filip Vercruysse

Verifed customer · 1 year ago

Top Company, Top Tour ! We did the 7 days tour (from Alps to Adriatic), from Bled to Piran in august 2024 ! It was the best tour made in years. Amazing landscapes and nature, great accommodations and food and perfectly organised. Daja did really a perfect job ! she was allways available for questions or suggestions ! I would recommend this tour to everyone.

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SHONA Goaman

Verifed customer · 7 months ago

Well organised, great route and lovely hotels.

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Karen Bergman

Verifed customer · 9 months ago

I thoroughly enjoyed this trip! The guides were professional and provided excellent leadership. They clearly know this country and the best cycling routes. I would definitely do another trip with them.

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