Ride Across Dorset

Four unforgettable days.

One extraordinary journey.

Experience Dorset from its rolling chalk downs to its dramatic Jurassic Coast on a fully supported cycling holiday unlike any other.

We'll take care of the accommodation, luggage, logistics and route planning, allowing you to enjoy one of England's most beautiful counties exactly as it was meant to be explored—by bike.

✔ Tour Highlights

Four days of guided riding
Four nights' accommodation
Luggage transported each day
Hand-picked accommodation
Home-cooked welcome dinner at Rose House
Spectacular Dorset scenery
Ride the Jurassic Coast
Durdle Door & Lulworth Cove
Studland and Old Harry Rocks
Chalk downs and ancient ridgeways
Small groups: come on your own, or with partner/friends
Fully supported throughout
Particularly suited to e-bikes

Monday

Welcome to Dorset

Arrive at Rose House in Iwerne Minster during the afternoon, settle in and enjoy a relaxed welcome with drinks and a home-cooked evening meal.

We'll introduce the week's adventure, check bikes and answer any questions before tomorrow's journey begins.

Tuesday – Day One

Into the Dorset Downs

Leaving Iwerne Minster behind, our adventure begins across the rolling chalk landscapes of North Dorset.

We'll climb to the panoramic views of Bulbarrow Hill before following ancient tracks through the Dorsetshire Gap and picturesque villages including coffee stop at Ansty.

A tasty picnic lunch will set you up for the afternoon - and progress permitting we will stop off for afternoon tea along the way.

The day finishes at Winyards Gap Inn after a wonderful introduction to Dorset's quiet countryside and hidden valleys.

Wednesday – Day Two

From Hills to the Sea

Today's ride takes us across to Broadwindsor, up and over Lewesdon Hill, then on through the beautiful Marshwood Vale before reaching the coast at Lyme Regis for lunch.

From there, we'll follow one of Britain's most spectacular coastlines, riding underneath Golden Cap - there highest point on the South Coast - and on towards West Bay with breathtaking sea views, dramatic cliffs and unforgettable scenery.

Finishing our day at Eypes and our next stop over Eypes Mouth Country Hotel.

Thursday – Day Three

Along the Jurassic Coast

Today showcases some of Dorset's most iconic landscapes.

Following the South Dorset Ridgeway, we'll enjoy magnificent views across Weymouth Bay, overlooking Abbotsbury and passing Hardy's Monument before we take some time out for a really fabulous lunch at The Wishing Well in Upwey.

In the afternoon we continue along the coast above Osmington and Ringstead before reaching the world-famous landmarks of Durdle Door and Lulworth Cove where we stay. Option of a sauna and swim in the cove itself.

Really a day where the views continue to give at every turn.

Friday – Day Four

The Purbeck Finale

Our final day takes us through the beautiful Isle of Purbeck, past Kimmeridge and over to Swanage, before climbing onto Ballard Down for spectacular views across Old Harry Rocks and Studland.

One last unforgettable section brings us up and onto Nine Ballard Down, with far-reaching views of Poole Harbour and then a final magnificent descent to Corfe Castle, where we'll celebrate the completion of our Dorset adventure before transporting you and your bikes back to Iwerne Minster.

This isn't simply a route across Dorset—it's a carefully curated journey through one of England's most beautiful counties, shared with like-minded cyclists and supported every step of the way.

PRICES:

£875 per person for dual occupancy: including 4 nights accommodation, dinner at Rose House, all breakfasts & packed lunches (other dinners and drinks not included), luggage transfers and collection/return to Iwerne Minster.

Single occupancy from £1,150