Dorset and the Jurassic Coast Cycling

From $882 per person

****# (91%) Based on 6 customer reviews
CC BY Paul Tomlin / flickr
  • Famous, fossil-filled Jurassic Coast: sheltered bays, deserted coves, stunning Blue Flag beaches
  • Rich rolling hills, patchwork fields, grass-covered cliffs dotted with Iron Age Forts and battle-worn coastal castles
  • Tranquil traffic-free cycling - electric bike option for hillier sections!
  • Traditional seaside resorts, historic market towns, quintessential English villages serving clotted cream teas!
  • Unique geology tracing 185 million years of history

What's included?

  • 5 nights, hotel-to-hotel
  • Departs Daily from 1 May '17 to 30 Sep '17
  • Full English Breakfasts included
  • Managed by Headwater appointed agent
  • Sustainability rating: 86%
  • Route notes and maps provided
  • High quality bikes provided
  • Optional electric bikes
  • Luggage transfers between hotels

Excellent for...

Dorset and the Jurassic Coast Cycling

Undeniably one of the loveliest counties in England, Dorset is frequently described as 'the best of both worlds' with fabulous beaches, magnificent cliffs, historic towns, unspoilt villages and wildlife-rich nature reserves. Captivated by its unique charm and outstanding natural beauty, Dorset has long been an attraction for artists, photographers, writers and film-makers, and its stunning coast was the awe-inspired setting for ITV's award-winning drama, 'Broadchurch'.

On this new 5-night holiday, the cycling alternates between traffic-free bridleways and undulating country lanes - don't worry, you can opt for an electric bike if you're nervous about tackling the hillier sections! For much of the time you'll be pedaling close to the UNESCO-listed Jurassic Coast, a 185-million-year-old shoreline of fossil-filled caves and stunning beaches and England's first Natural World Heritage Site. And, as the cycling distances are quite short, you'll have plenty of time to relax on the beaches, go swimming, enjoy leisurely lunches at the numerous seaside cafes where the freshest of seafood comes straight off the boats. You'll enjoy exploring inland too where, set back from the sea and nestled among low fertile hills, lies an equally contrasting and colourful landscape: from historic market towns to centuries-old fishing villages to super-rich Sandbanks where you'll find some of the most expensive real estate in Britain!

The range of places you'll be staying in are among the best in the region, including a boutique beachfront B&B in Weymouth and a lovely old Georgian townhouse in the centre of historic Dorchester. Breakfasts are included everywhere, however, with so many fine restaurants, tempting tea-rooms and great pubs on your doorstep, we've left other meals up to you.

Day-by-day itinerary

Day 1 Arrive in Weymouth

We meet you at Weymouth train station and take you (5 minutes) to your boutique B&B right on the town's splendid Georgian Esplanade overlooking its amazing sandy beach - first put on the map in 1789 when Mad King George III used an off-the-wall 'trolley-cum-bathing machine' to take his first Royal dip! Time permitting, explore the bustling C17 harbour and adjacent C19 Northern Fort - its stunning views and excellent British Naval Museum makes it one of Weymouth's most visited attractions.

Day 2 Weymouth to Dorchester 21 miles

A gentle cycle west this morning along the scenic shores of Radipole Lake - a designated RSPB reserve of whispering reeds and migrating waterfowl - then on to Chesil Beach where The Dambusters' 'bouncing bomb' was developed. You'll pass the world-famous Swannery - nesting ground for over 600 mute swans - en route to the postcard-pretty village of Abbotsbury. Lunch perhaps on the lawn of the delightful Abbey House Tea Rooms which afford uninterrupted views of the Tithe Barn and Abbey ruins below and St Catherine's C14 chapel on the hillside in the distance. Keen gardeners shouldn't miss the village's award-winning sub-tropical gardens - 20 magnificent acres of walled woodland with rare and exotic plants from all over the world. Continuing along quiet country lanes, fantastic sweeping views of the timeless Dorset countryside open up as you climb gradually to Hardy's Monument, a 72-ft high landmark built in 1844 in memory of Vice Admiral Sir Thomas Hardy, captain of HMS Victory and a commander at the Battle of Trafalgar. Your final stretch is an exhilarating downhill whizz through the peaceful Bride Valley to the great historic town of Dorchester where you stay overnight.

Day 3 Dorchester to Wareham 47km/29 mi

It's lovely tranquil pedaling this morning as you follow pretty riverside paths and bridleways east through rolling countryside to the sleepy village of Moreton, where T.E. Lawrence (better known as Lawrence of Arabia) lived nearby and is now buried in the cemetery. From here, you head south, to the stunning Jurassic Coast, get off the bike and walk to massive Durdle Door - one of the most photographed rock arches in the world - before pedalling on to gorgeous Lulworth Cove for lunch. Enjoy a swim from the beach or step back through millions of years of the Earth's history at the renowned Heritage Centre before continuing on to the pretty riverside market town of Wareham, home for the next two nights.

Day 4 At Wareham

Captured by the Vikings in 876, Wareham's fascinating history dates back nearly 2000 years. Explore the remnants of its Saxon walls and churches, and watch the world go by on the quay - once a busy river port, now a popular meeting point and site of the town's weekly market. In the afternoon, perhaps take the bus to Swanage, a small Victorian seaside town overlooking one of the most beautiful bays in the country.

Day 5 Wareham to Sandbanks/ Poole 30km/19mi or 42km/26.5 mi

Built by William the Conqueror and destroyed by Cromwell's vengeful troops during the civil war, the dramatic ruins of Corfe Castle - now a National Trust property and the setting for several historical feature films - stand at the gateway to the Isle of Purbeck and its surrounding hills. Wander around the village - described as one of England's most beautiful - before cycling along pretty bridleways to the gorgeous white sands at Studland. The dunes here are a protected National Trust nature reserve and home to rare species of bird and plantlife. Taking your bike with you, it's just a short hop on the chain ferry across to exclusive Sandbanks and your waterfront hotel. Optional circular cycle (or bus) for those wanting to visit neighbouring Poole - a beautiful coastal town whose natural harbour is the second largest in the world.

Day 6 Leave Sandbanks

You may want to spend extra nights at leisure in Sandbanks, otherwise, after breakfast, your hotelier will arrange a taxi to Poole station at a time to connect with your onward travel arrangements.

For a longer tour, why not consider combining this with our Backroads of Brittany Cycling

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking. You can call our sales team on 1-800-567-6286 to discuss accommodation options.

If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day. Please contact us on 1-800-567-6286 for further details.

B+B Weymouth   (3 Acorn)

Weymouth Esplanade, location of B+B Weymouth

Situated in a Grade II listed Georgian building right on the seafront along Weymouth Esplanade is B+B Weymouth, a privately owned bed and breakfast offering guests boutique accommodation in the centre of a historic seaside town. Rooms here offer a clean, minimalist design and there is a tastefully decorated lounge area with leather couches, free tea and coffee, and floor to ceiling windows, which offer spectacular views over Weymouth Beach.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar
  • Safe
  • Tea/coffee facilities

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Casterbridge Guest House, Dorchester   (3 Acorn)

Lounge at Casterbridge

The Casterbridge is a charming, wisteria clad Georgian town house in the centre of historic Dorchester with Period furnishings, drawing room, bar/library, conservatory and courtyard garden.

There are 9 bedrooms, most of which have been recently renovated in a traditional style.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • Hairdryer
  • Wifi hotspot
  • Television
  • Tea/coffee facilities

Nearby facilities:

  • Banking / cheques cashed
  • ATM / Cash machine

The Red Lion, Wareham   (3 Acorn)

Red Lion, Wareham

Ideally located in the centre of historic Wareham, a town which dates back to Saxon times, is the family run Red Lion Hotel. The old inn was extensively refurbished in 2011 but has retained much of its charm and period features. The hotel offers a number of lovely rooms decorated in a contemporary style with new bathrooms and Egyptian cotton sheets, and the downstairs has a spacious bar, a cosy snug and a more formal restaurant.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar
  • Safe
  • Tea/coffee facilities

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Harbour Heights , Poole   (4 Star)

Harbour Heights Hotel, Poole

Ideally located between Poole and exclusive Sandbanks, with scenic views over the world's second largest natural harbour, the Harbour Heights offers boutique rooms, an award-winning restaurant and stylish cocktail bar. Rooms have a subtle nautical theme and each en-suite room has a spa bath! The Brasserie here serves an impressive seasonal menu and there is also a large, landscaped terrace with panoramic sea views for al fresco dining.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar
  • Air conditioning
  • Safe
  • Tea/coffee facilities

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Travel options

Transfer to the Hotel from Weymouth train station at the start of the holiday.

Please call our sales team on 1-800-567-6286 or email to arrange connecting flights.

Customer reviews

Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus, of course, an overall rating and comments about their holiday.

Any feedback collected is posted straight to our website - totally unedited. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Reviewed by Mrs McInnes on 03/07/2016

A wonderful exploration of the Dorset countryside.Very friendly locals,good hotels,very good cycles provided by Roy Griffiths from sign post cycling who gave us an extra days use of the cycles at no charge.

Reviewed by Mr Crossland on 09/09/2015

The route and places visited were superb. There were a variety of options for sightseeing and plenty of time to see them properly. We enjoyed the variety of challenges for cycling with some long off road sections, a few steep inclines and practically no riding on busy roads. The written instructions were very helpful. As with other cycling tours we have taken it would have been beneficial if the route was pre-marked on the map provided and perhaps a few more cross references between the map and written instructions. If arriving by car, it is most important to phone Roy the local representative to help you sort the complex parking arrangements in Weymouth Swannery carpark. He is an excellent ambassador for Headwater. The Dorchester Sienna Restaurant was superb and visiting the Roman house is a MUST. When leaving Dorchester the route follows the Northern bank of the River NOT the right bank as written in the guidance notes. During the Wareham free day, we visited Swanage via the bus and steam railway. We visited the pier and saw a magnificent Tall ship and walked to the headland for good views of the Isle of Wight. We continued to walk on the Victorian coastal path to the excellent Durlston Castle for lunch and fantastic panoramic views. The Harbour Heights at Poole was the quality of Hotel we were expecting and provided superb views across Poole harbour. We returned to Swanage bus station by the half hourly bus service. Michelle from the Weymouth B&B found the cheapest (Fleetline) taxi return from Poole. This is a highly recommended way to return to Weymouth with suitcases.

Reviewed by Mr Bailey on 31/08/2015

We went to Dorset in the wettest week of the year, so only managed half a days cycling. The local rep could not have been more helpful, driving us along the routes we were supposed to be cycling and pointing out the sights to see. Disappointed that in spite of phoning Headwater with our time of arrival, this was not communicated to the rep so we had to walk to our hotel. I am not sure this particular Headwater holiday is great value for money, as travel and dinner are not included, but I might be less critical had we had some decent weather.

Reviewed by Ms Singleton on 24/08/2015

We loved our 4 day cycling holiday in Dorset. The B&Bs were excellent. The Kings Arms a little dated and the staff a little bored The Red Lion and Harbour Heights were perfect as were the staff. We definately want to do this again. Roy was so informative. The whole experieince was great. Thank you so much Del and Jackie

Reviewed by Ms Skinner on 09/08/2015

We were a group of three; two elderly parents and a sixteen year old son. We all thoroughly enjoyed the routes taken, places stayed and food eaten. It is a tricky task to ensure the enjoyment of three people with diverse interests, (my husband is an architect and loves old buildings!) so , I am very pleased that this holiday was such a success. Special mention of Roy who spent time and care ensuring that all was in order... And warned us about the steep climb up to Hardy's monument! I would recommend this holiday to anyone. The Dorset countryside is unbeatable, stunning and truly beautiful.

Reviewed by Mr Wignall on 31/07/2015

Jurassic Coast cycling offered a superb variety of classic British countryside, thatched cottages, country lanes, ruined castles, sandy beaches and of course village greens with pubs. A few short hills provided brilliant views over Poole bay and the sea beyond and the route was a good mixture of quiet lanes, gravel tracks and minor roads. We mentioned a small tweek to the route notes around Corfe Castle to the rep you may suggest this amendment in the future. Unfortunately it rained for 4 days out of the 5 but thats the British summer for you !! How can we submit photos if we don't do Facebook?

Departure dates & prices

May 2017 departuresTour only 
May 1$913
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Aug 28$913
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September 2017 departuresTour only 
Sep 1$913
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Sep 4$882
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Holiday details

Holiday type

Self-guided cycling, hotel-to-hotel. Managed by Headwater appointed agent.


Daily from 1 May '17 to 30 Sep '17, for 6 days (5 nights).


Full English Breakfasts included.

Other details

Please see our Planning your holiday and What's included in the price? pages for additional information. Please call us for single room supplements, room upgrade options and child prices.

Starting your tour

Transfer to the Hotel from Weymouth train station at the start of the holiday.

Enquire about this holiday

Simply complete the form below and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and additional information.

We'd like to keep you informed of our latest news and special offers. Please tick here if you'd rather not receive our free e-newsletter.
We can call you when it's most convenient for you, or contact you by email if you'd prefer. Morning calls will be between 9:00-13:00, afternoon calls between 13:00-17:00, and evening calls after 17:00.
Let us know any queries you might have about departure dates, similar holidays or tailor-made options.


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