London - Havant - Isle of Wight - Worthing - London is fully booked London - Havant - Isle of Wight - Worthing - London

London - Havant - Isle of Wight - Worthing - London

12th August 2021 - 16th August 2021 (5 days)

A moving on tour averaging 55 miles per day and 2,500ft of ascent with 2 'challenging' days on Day 1 and Day 3 - although we can ride that day's Isle of Wight circuit without luggage, making the riding easier. Day 2 is basically a leisurely transfer to the Isle of Wight, and involves using two ferries, and could feature as few as 16 miles, leaving time to explore Sandown, or go for a swim, after arrival. On Day 4 we return to Portsmouth and take a mainly flat coastal ride along to Worthing. Highlights include The Devil's Punch Bowl, Isle of Wight, the South Coast from Portsmouth to Worthing and the iconic Box Hill climb.

  • Holiday Type Guided
  • Tour Manager Peter Mastenko
  • Grade Challenging
  • Booking Status Fully Booked
  • Accommodation Hotel
  • Board Basis Some Meals
  • Travel Arrangements Ferry
  • Road / Off Road Road
  • Holiday Style Moving-on
  • Vehicle Support Carry Own Luggage
  • Holiday Ref 03654


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London - Havant - Isle of Wight - Worthing - London is fully booked London - Havant - Isle of Wight - Worthing - London

Thursday 12th August

We meet outside Surbiton Station at 9.30am. A Travelodge in Kingston or a Premier Inn at Tolworth are nearby if required. We ride via the Surrey Hills (approx 550ft ascent to Staple Lane at 650ft and Combe Lane descent) and on to the Devil's Punch Bowl (approx 600ft of ascent to 866ft), and a long descent, stopping at Grayshott for a cafe lunch, before continuing to the South Downs National Park, with a few testing climbs (ok to walk!), before descending to Rowlands Castle (refreshments) and to Havant and the Bear Hotel. 71 miles. Total ascent 4,078ft. Stay 1 night. Meals: None

Friday 13th August

We cycle to Portsmouth Harbour via Hayling Island and Eastney Ferry. 12 miles. We take the Fastcat to Ryde, and cycle via Brading  to Sandown and the Wight Bay Hotel. 9 miles. Total for day 21 miles. Total ascent 500ft. The remainder of the day is free to explore Sandown, go for a swim, or a bike ride. Stay 2 nights. Meals: B

Saturday 14th August

A clockwise 'Round the Island' ride. We head south through Sandown, Lake and Shanklin, climbing and then descending to Bonchurch, before joining the 'official' route near Ventnor. We plan to ride to the Needles, and cycle back via Yarmouth , Cowes, Wootton, and Bembridge to Sandown. 65 miles. Total ascent 3,904ft. Meals: None

Sunday 15th August

We cycle to Ryde Pierhead and take a Fastcat ferry back to Portsmouth Harbour. Once back on the mainland we return to Havant, via the Hayling Island ferry, and continue east via Chichester, Bognor Regis, Littlehampton to Worthing. 60 miles. Total ascent 1,120ft. Stay 1 night close to the seafront at the elegant Chatsworth Hotel. Meals: None

Monday 16th August

Return to Surbiton featuring a short coastal ride to the Shoreham Gap, where we commence a route North via the lanes, with plenty of potential refreshment stops for tired legs, passing several nice villages including Partidge Green and Rusper in West Sussex and Newdigate in Surrey, en route to a climb of the iconic Box Hill in the North Downs, if desired, and a descent from Headley via Epsom back to Surbiton Station, where the holiday will end. 56 miles. Total ascent 3,037ft. Meals: B

Meals: B = Breakfast

The above itinerary should be treated as an indication of what is to be accomplished during the tour and not as a contractual obligation.

Accommodation & Meals

On 2 nights, accommodation will be in a 3-star hotel with en suite facilities. On 2 nights, accommodation will be in a 2-star hotel with en suite facilities. All rooms are based on 2 persons sharing, with breakfast included at the first and fourth overnights. No other meals are included in the tour price.

Vehicle Support

No vehicle support is provided. Participants are expected to carry their own luggage. You are encouraged to travel as light as possible.

Travel Insurance

Obtaining travel insurance is optional for UK residents as your Cycling UK membership provides third party cover. However, this does not cover any other risks such as cancellation charges, personal injury or lost property. We therefore strongly recommend that suitable insurance is taken out to safeguard against such risks. Members who do not reside in the UK are not covered for third party and are advised to obtain suitable cover before leaving their normal residence. If you already have an annual policy, you may need to confirm that it will cover a UK holiday or make provision for it to do so.


The price of £310 is based on a minimum number of 7 people taking part in the holiday; please note Booking Conditions, clause 3. If there are insufficient bookings by 3rd June 2021, we will contact you and return all monies paid.

Price Includes

  • 4 nights hotel, sharing room
  • 2 breakfasts
  • CTC Cycling Holidays & Tours costs

Price Does Not Include

  • Travel to the start or from the end of the tour
  • Fastcat Isle of Wight ferry (allow £28)
  • Eastney ferry (allow £5.50)
  • Breakfasts on two days
  • Dinners, lunches or refreshments during the day
  • Entry fees at any attractions visited
  • Any other personal expenses
  • Travel Insurance
  • Single occupancy supplement (£188, subject to availability)

Payment Schedule

A deposit of £31 per person is payable upon booking, with the final balance of £279 per person to be paid ten weeks prior to departure, by 3rd June 2021.


Should you be forced to cancel your booking for any reason you must notify us in writing. Cancellation charges are as follows:

Written notice received:

Before 3rd June 2021

From 3rd June 2021 through to departure


Cancellation charge:

Deposit (£31)

100% (£310)

The Area Covered By The Holiday

The rides traverse the Surrey Hills AONB, the Weald, the South Downs National Park, the Isle of Wight, and the South Coast between Portsmouth and Worthing, before returning to London. Highlights include:- The Devil's Punch Bowl - legend has it that the Devil scooped up a handful of earth and hurled it at Thor, God of Thunder, to create the Punch Bowl. The Isle of Wight - with its fabulous scenery and breathtaking views, boasts miles of stunning coastline views and beaches. We will take a catamaran ferry from Portsmouth to Ryde, and enjoy 2 nights on the Island and a 'round the Island' cycling day. We pass through Hayling Island, Chichester, Bognor Regis, Littlehampton and Worthing. Finally the last day includes the Shoreham Gap and we ride the iconic Box Hill climb. Wherever possible, quieter roads are followed.

Rides & Rest Days

Apart from any refreshment breaks, most of each day will be spent in the saddle, apart from Day 2, where much lower mileage is planned. All of the route is on tarmac roads, using a mixture of lanes, B-Roads and A-Roads. As usual with rural roads, please be aware of any loose gravel, debris, potholes, uneven surfaces, drains, etc. Take care on any steep descents with blind bends!
The Tour Manager will lead at a relaxed pace of 10 - 12 mph on the flat, tackling any climbs at a slower pace - we can take hills at our own pace, then re-group at the top of climbs. Any faster riders are welcome to ride ahead at their own pace, assuming they feel confident to follow the (supplied) GPS route, and outline route instructions, which will be supplied in advance. As no back-up vehicle is provided, it is important that each rider feels confident and is fit enough to undertake this tour whilst carrying their own spares and a minimum luggage.

Group Information

The maximum number of participants will be 10 excluding the Tour Manager.

Weather & Clothing

Weather in the South East in early August should be ideal for summer cycling, with average temperatures on the Isle of Wight, for example, being 17C and an average of 5 or more dry days per week and 14.5 hours of daylight. You should dress suitably according to the weather forecast just before the tour. Aside from your on-bike attire, a lightweight packable waterproof jacket is always useful to carry, and some lightweight clothing and sandals to wear in the evening. Don't forget the sun protection, and helmet if you wear one. Also some lightweight clothing and sandals/flipflops to wear in the evening.

Cycles & Equipment

A lightweight touring or road bike is suitable for this tour. You should ensure your cycle is well maintained, paying particular attention to wheels, tyres and brakes. A low bottom gear (e.g. small chainring the same size or smaller than the largest cog on your rear wheel) is recommended. If you are unsure about gears, please discuss with the Tour Manager. Mudguards are optional but show courtesy to those who are following you in wet weather. Lights are recommended but might not prove essential. New tyres are recommended of at least 25mm diameter. Participants will be expected to carry each day sufficient spares and tools to deal with punctures and minor repairs.
A pannier, or rack top pack or bar bag will be useful for carrying wet weather gear, lightweight clothing for the evening, phone, snacks and your map. Each participant is expected to bring, and carry, all of their own clothing, personal items and spares. You are advised to do some riding before the tour with a similar load to that which you will be carrying during the tour to get a feel for how your bike will handle.
Helmets are recommended but it's your personal choice.

Maps & Guides

The links to the route and GPX file downloads on Ride with GPS will be provided in advance of the tour as well as a list of all the places we cycle through in order of visit. It's also useful to carry an outline map of the areas we will cover, perhaps taken from an atlas. The addresses, phone numbers and locations of the accommodation will be supplied. You should carry these, and a mobile phone, if you use one.