Beautiful views towards St. Catherine's Point Taking a break above Alum Bay
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Isle of Wight

Take a self guided walking or cycling holiday on the Isle of Wight

Where can you go in the British Isles that is close enough to London to not require expensive train journeys, a place which in many ways exists in its own time warp, where you can walk to beautiful scenic and historical places on scenic coastal paths and across hilly grassy down land, through ancient woodlands, past rustic farms? This has to be the Isle of Wight.

The Isle of Wight is a limited holiday opportunity; you only have about another 4000 years before the island disappears into the sea! Parts are going at rates of 3.5 metres a year….. See it while you can!

Famous for its sailing regattas, for the white chalk cliffs and the stacks called The Needles and for the coloured sands at Alum Bay. The Island may be a bit of a cliché in British tourism, but it exists in its own time. Beyond the big tourist towns of Shanklin and Sandown, and the sophistication of Cowes harbour, everything is on a manageable scale - no huge towns, or big industrial blights, but long chalky downs, sandy beaches and enchanting woodlands. Seaside rock, ice cream and fish ’n’ chips of course, but also great pubs and restaurants, quiet paths, historical churches and gems of villages.

Let’s face it, if it was good enough for Queen Victoria, its good enough for most of us! After all, Queen Vic despite ruling a quarter of the Earth and being Empress of India, elected to spend her holidays on the Isle of Wight where she had her husband build a little holiday cottage called Osborne House- her little ‘pied de terre’. She painted and sketched the nature, rode horses, went for long walks, went swimming and even spent her last days there.

When to walk & cycle on the Isle of Wight

We recommend taking a walking or cycling holiday on the Isle of Wight either between April to late June (before the UK schools break up) or between September and October. The spring and early summer often has low rainfall and beautiful spring flowers within the woodlands with bright emerald leaves on the trees, while the autumn period has a more rustic golden charm. Of course sea fogs can be notorious and can roll in at any time!

It is best to avoid the heaving summer ‘bucket and spade’ season and the August Cowes weeks – although the trails can be quiet, resorts and towns are very busy. There are several music, walking and cycling festivals taking place in May, so similarly that month can vary in terms of busyness. 

Walking holidays on the Isle of Wight

On our walking holiday on the Isle of Wight you will have the opportunity to circumnavigate the island by the coastal path which does not follow the coastline all the time, but except for some sections after heavy rain the walking is generally easy going and there is some road walking involved. You will of course walk through tourist hotspots to then soon be in peaceful countryside once again. 

Cycling holidays on the Isle of Wight

Our cycling holiday on the Isle of Wight is an easy going ride circumnavigating the island on the Taste Round The Island Bike Route, which we follow, with some variation for its entirety over three cycling days. This keeps the days almost equidistant in length. The rides are undulating and only on the last day will you find it particularly hilly. 

It is a ride that will appeal to novices, and those used to cycling will find it easy and enjoy time spent visiting various sights on the ride. So although the days are quite short, you can easily spend much of the day visiting Osbourne House, or the Needles etc. The second cycling day can be made shorter and easier by missing out cycling to the Needles and over hilly Tennyson down.

Getting to/from the Isle of Wight

It is so easy (and cheap!) to go somewhere as different as the Isle of Wight. An hourly train from London Waterloo takes you directly to Portsmouth Harbour (1.5-2 hours), where you can seamlessly walk on to the passenger ferry. Less than half an hour later, the ferry arrives at an old pier, where an antiquated City and Metropolitan tube train serves as the main train into Ryde, the island’s largest town. Those who can’t get there quickly enough can take the only scheduled passenger hovercraft service in the world, which plonks you onto the beach by the esplanade. Both ferry and hover options cost around £16.

Why travel with us

Personal Experience

We've been walking and cycling the planet for over four decades and are passionate about delivering exceptional service. Combined, we’ve travelled to virtually every corner of Europe, and are eager to share the many benefits of travelling on foot or by bike.

Great Value & Quality

Our well priced trips offer great value for money. Included in your package are comprehensive route notes, maps & guide books along with bag transfers and locally run accommodation. We take the stress out of organising your holiday.

Self-Guided Specialists

We have been operating active self guided holidays since 1973. We handle all the necessary logistics so that you can relax and explore your destination at your own pace. Many of our tours depart daily, giving you even greater flexibility.