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Isle of Wight Bike Tour

5 days / 4 nights

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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

Season

From April to October

Fitness level

2/5

Tour type

Gravel / E-bike

Google ReviewsTripAdvisor Reviews
  • 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.

Our Bikes

To ensure the best possible experience on your cycling adventure, we offer top-quality bikes for rent. Our fleet features the latest models, meticulously maintained for both performance and comfort.

To match each rider with the right equipment, our team will also assist you in selecting the most suitable bike based on your physical profile, personal preferences, and the technical requirements of the tour.

Gravel Bikes image 1

Gravel Bikes

Best for: Mixed-surface rides, backroads, and light trails


These are premium gravel bikes built to handle a mix of paved and unpaved terrain. They come with wider tires for extra grip, disc brakes for reliable stopping, and stable geometry that keeps things comfortable on longer rides. A great choice for exploring backroads, forest trails, or varied surfaces with confidence and ease.

Touring E-Bikes image 1

Touring E-Bikes

Best for: Comfortable trekking, touring, longer distances, and hilly routes


These pedal-assist electric bikes are designed to make riding easier and more enjoyable—especially on longer or hillier routes. They come with powerful mid-drive motors, long-lasting batteries, and comfortable riding geometry for smooth support across varied terrain. With intuitive controls and quality components, they’re a great choice for riders who want extra assistance without giving up the feel of a real ride.


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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+6
Top Rated Brand
Greg Martin's profile photo

Greg Martin

Verified customer

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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SHONA Goaman's profile photo

SHONA Goaman

Verified customer

Well organised, great route and lovely hotels.

Karen Bergman's profile photo

Karen Bergman

Verified customer

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.

Amy Berger's profile photo

Amy Berger

Verified customer

Great trip! Klemen set up our trip perfectly. When we needed him he was there. The hotels were excellent. The biking a blast. We did a 5 day self guided tour. Do it!!

enric tomas's profile photo

enric tomas

Verified customer

Good organization, we made the trip without any setbacks, and if there were any (a reservation that couldn't be found), they were able to resolve it satisfactorily. Recommended.

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Adrian Wee

Verified customer

Klemen was very responsive and handled everything from start to finish. Route planning was customised to our ability and requirements. No cookie-cutter itinerary here. Accomodation selection was excellent. Absolutely would use this company again.

All available guidance options

Self-guided

Those who like a good adventure and limitless flexibility should go on a self-guided cycling holiday...

HANDPICKED ADVENTURES

HANDPICKED ADVENTURES

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SELF-GUIDED TRAVEL

SELF-GUIDED TRAVEL

Explore independently and with confidence while we keep everything running from behind the scenes.

VALUE YOUR TIME

VALUE YOUR TIME

With everything on your plate, let us handle the vacation planning, so your valuable time stays exactly where you need it.

TRUSTED BY MANY

TRUSTED BY MANY

We are a financially protected company operating since 2014, and with thousands of satisfied customers in the past, we still put you first.

from 1.000 € /person