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Dorset and the Jurassic Coast Cycling

Dorset and the Jurassic Coast Cycling

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  • Holiday typeSelf-guided cycling
  • Duration5 nights
  • Accommodationhotel-to-hotel
  • Activity level
  • From $925per person, tour only
  • Departures
    Daily from 22 Aug '18 to 30 Sep '19
  • What your holiday price includes
  • 5 nights hotel-to-hotel accommodation in a mix of and hotels
  • Full English Breakfasts
  • Management by your local Headwater-appointed agent
  • Route directions and maps
  • High quality bikes
  • Luggage transfers between hotels
  • Optional Upgrades
  • Excellent choice for
  • Flora & fauna, bird spotting opportunities, art & history, swimming opportunities, couples, coastal routes, lake & river routes
      from 14 reviews

Mrs Watson says...
An extremely enjoyable holiday in beautiful countryside with breathtaking sea views. the local agent Roy was very helpful, friendly and cheerful. The only ...
Read reviews »


Dorset and the Jurassic Coast Cycling

  • 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
  • Traditional seaside resorts, historic market towns, quintessential English villages serving clotted cream teas!
  • Unique geology tracing 185 million years of history

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 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 lovely old Georgian townhouse in the centre of historic Dorchester, a family-run inn in Wareham and a luxurious hotel with panoramic sea views near Sandbanks. 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.

We're here to help

If you have any questions about this holiday call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Day-by-day itinerary

We're here to help

If you've any questions about this holiday call our sales team on 1-800-267-3347 , or email usa@exodustravels.com

Day 1 Arrive in Weymouth

We meet you at Weymouth train station and take you (5 minutes) to your 3* hotel, close to 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 Nothe Fort - its stunning views and excellent British Naval Museum makes it one of Weymouth's most visited attractions. (Staying at Hotel Rembrandt, Breakfast only)

Day 2 Weymouth to Dorchester 34km/21.5mi

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. (Staying at The Casterbridge, Breakfast only)

Day 3 Dorchester to Wareham 47km/29mi

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. (Staying at The Red Lion, Breakfast only)

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. (Staying at The Red Lion, Breakfast only)

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

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. (Staying at Harbour Heights Hotel, Breakfast only)

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.

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. 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.

To find out more call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Hotel Rembrandt, Weymouth

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Situated just a few minutes' walk from Weymouth's seafront esplanade, beautiful sandy beach and town centre, the Hotel Rembrandt, part of the Best Western group, offers 78 comfortable rooms with contemporary decor. All rooms offer an ensuite bathroom, tea and coffee-making facilities, 24-hour room service, flat screen TV and fibre Wi-Fi.

Guests have complimentary use of the hotel's Leisure Club, an ideal place to relax that features a heated swimming pool, gym, sauna, steam room, spa bath and sun bed. For those aching muscles, there is also a spa treatment room (open Mon-Sat) and a choice of massage and health & beauty treatments (payable locally).

After plenty of sea air to swell your appetite, the hotel's Gallery Restaurant offers wholesome, freshly prepared dishes using locally sourced ingredients. The Gallery Bar is ideal for pre- or after-dinner drinks.

Find out more on the hotel website and read customer reviews on Tripadvisor.

DatesExecutive RoomSuperior Room
01/05/2018 - 30/09/2018£14£28

All prices shown above are valid from 30/04/2018. Executive Rooms offer more space as well as upgraded toiletries, 42' LED Flat Screen Television and a docking station/speaker. Superior Rooms offer more space, bathrobe & slippers, two flat screen TV's, a 2-seater sofa, fresh fruit and flavoured water, minibar/fridge and a pillow menu.

Please contact us for extra night prices.

The Casterbridge, Dorchester

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.

Wessex Royale, Dorchester

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The Best Western Wessex Royale Hotel is situated close to the Jurassic Coast. It is an old coaching inn built in 1756, which has flawlessly been updated with comfortable modern furnishing. The hotel is located close to the Dorset County Museum and Dorchester Arts Centre.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.

The Red Lion, Wareham

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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 and the downstairs has a spacious bar, a cosy snug and a more formal restaurant.

Read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.

Springfield Country Hotel , Wareham

Just outside Wareham the Springfield Country Hotel is set in 6 acres of beautifully landscaped gardens, and offers both indoor and outdoor pools.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.

Harbour Heights Hotel, Poole

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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. Guests of the Harbour Heights Hotel have full use of the spa at sister property, the Haven Hotel.

Find out more on the hotel website and read customer reviews on Tripadvisor.

DatesHarbour ViewHarbour View with BalconyHarbour View with Juliette Balcony
01/05/2018 - 30/09/2018£16£18£24

All prices shown above are valid from 18/11/2017. Harbour View doubles have views over Poole Harbour. Harbour View doubles with balcony have views and a balcony over Poole Harbour. Harbour view deluxe double with Juliette balcony rooms are more spacious and offer a Juliette balcony overlooking Poole Harbour.

Please contact us for extra night prices.

Haven Hotel, Sandbanks

Swimming Pool IconHair dryer iconNEARBY:

The Haven Hotel is on the very tip of the Sandbanks peninsula at the entrance to Poole Harbour and offers incredible views across the water all the way to the Isle of Wight! Rooms are tastefully furnished and well equipped and the hotel has a fantastic restaurant and bar. It also offers guests free use of the impressive spa facilities which include indoor hydrotherapy pools, sauna and steam room, outdoor heated pool, jacuzzi and a sun lounger area. With sea views and a private entrance onto the beach, you can hear the waves crashing as you recline with a glass of wine.

Find out more on the hotel website and read customer reviews on Tripadvisor.

DatesSea ViewHarbour View/Sea View with BalconySuite with BalconySea View Deluxe with Balcony
01/05/2018 - 31/10/2018£14£16£20£24

All prices shown above are valid from 20/11/2017. Supplements are per person per night based on 2 sharing. Sea view and harbour view rooms are the same size as the standard rooms but with sea view or harbour views; the sea view double with balcony is also of the same size but comes with balcony, the Suite is a larger room with separate lounge area and balcony.

Please contact us for extra night prices.


Transfer from Weymouth train station at any time (5 mins) included and back to Poole train station (10 mins) payable locally.

Please call our sales team on 1-800-267-3347 or email usa@exodustravels.com to arrange connecting flights.


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 an overall rating and comments about their holiday.

Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Mrs Watson, 25/07/2018

An extremely enjoyable holiday in beautiful countryside with breathtaking sea views. the local agent Roy was very helpful, friendly and cheerful. The only problem was not having enough time to see all of the recommended sites but that will depend on the speed of the cyclists! Maybe a longer holiday with less stop overs would be the answer!

Mrs Farr, 13/09/2017

We had a good time and enjoyed the area, we were also lucky with the weather. The OS map was very helpful.

Mr Allan, 21/07/2017

Excellent area for cycling - mainly off road and local roads - but quite hilly. Good scenery, lovely villages, plenty of interesting tourist opportunities. Good pubs and tea shops.

Mr Warden, 20/07/2017

90% of the ride is on quiet lanes and bridal paths which made the ride more pleasurable. The first hotel (b&b) wasn't bike friendly as there were a flight of steps then two heavy sprung doors which made it difficult to get in and out. We did have a direction mistake but once we spoke to Roy this was soon resolved , luckily we hadn't gone too far in the wrong direction. Overall we had a great time and thoroughly enjoyed getting away to the fabulous Dorset countryside. We will defiantly be back

Mrs Molloy, 11/07/2017

The booking process was easy and the staff were very helpful answering any queries. The representative in Weymouth was very informative about the area and explained each day's cycling, what to see and where to visit. The cycling routes were a joy, they were very well planned and were an excellent way of discovering Dorset especially if it was the first time visiting the area.The electric bikes were of good quality.Our bags were transferred to each hotel, placed in our room before we arrived at each destination which was a bonus. Overall, it was a lovely holiday.

Mrs O'Sullivan, 10/07/2017

The Dorset cycle was very interesting and varied, with castles and historical sites, places of literary interest, beaches, fishing ports, and beautiful countryside. Routes were very well planned and signposted. Plenty of good restaurants and tearooms (recommended by the local Headwater guide).

This was our fourth cycling holiday with Headwater (plus 2 walking and 1 canoeing) but our first in England and our first with e-bikes. The towns of Weymouth, Dorchester, Wareham and Poole are all worth visiting.

This is a great trip for a short cycling tour - only three days cycling.

Mr Wotton, 19/06/2017

Great holidays my first cycling one and lots of fun

Mrs Macdonald, 15/05/2017

Cycling in South Dorset on decent bikes staying in excellent hotels/hostels is a great experience. The countryside is awesome and the cycle routes though challenging enabled us to enjoy it without killing us.

Mrs McInnes, 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.

Mr Crossland, 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.

Mr Bailey, 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.

Ms Singleton, 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

Ms Skinner, 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.

Mr Wignall, 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?

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday. Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

  • Aug
  • Sep
Aug 2018 Tour only Availability
21st Aug US$1005 Check availability
22nd Aug US$1005 Check availability
23rd Aug US$1005 Check availability
24th Aug US$1005 Check availability
25th Aug US$1005 Check availability
26th Aug US$1005 Check availability
27th Aug US$1005 Check availability
28th Aug US$975 Check availability
29th Aug US$975 Check availability
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Sep 2018 Tour only Availability
1st Sep US$975 Check availability
2nd Sep US$945 Check availability
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4th Sep US$945 Check availability
5th Sep US$945 Check availability
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24th Sep US$945 Check availability
25th Sep US$945 Check availability
26th Sep US$945 Check availability
27th Sep US$925 Check availability
28th Sep US$925 Check availability
29th Sep US$925 Check availability
30th Sep US$925 Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Please contact us for child prices.

Holiday type
Self-guided cycling Managed locally by Headwater appointed agent.

Daily from 21st Aug 2018 to 30th Sep 2018, for 5 nights.

Full English Breakfasts

Tailor-made travel

Tour only
Transfer from Weymouth train station at any time (5 mins) included and back to Poole train station (10 mins) payable locally.

How to book

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

We are ATOL registered We are an ABTA member
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