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Classic Cotswolds Cycling – 6 Day Private

From £2288 pp

England, The Cotswolds

5 nights/6 days

Private tour for 2-6

Classic Cotswolds Cycling – 6 Day Private


What You'll Do

Get to know the Cotswolds like never before, on a bespoke, 6 day private tour that, as well as taking you along some of the best cycling roads in the UK, gets you off the beaten track and under the skin of the region, as you discover the best pubs, the traditional cuisine, the fascinating history and the little local gems that make this corner of England so special.

This 5 night cycling tour will take you along the most beautiful, and the quietest, roads in the Cotswolds, and in that time spent cruising from bustling market town to poetically beautiful village, it will feel as if you have stepped back in time into an age where the only signs of industry are drystone walls and sheep.

Fill your days with unique activities tailored to you, from discovering local cuisine, stopping for some wild swimming, exploring the birthplace of Churchill and the stunning grounds of Blenheim Palace, or gazing at a view of 16 counties from the imposing Broadway Tower.

You’ll cover the big World Heritage Sites – the Queen’s residence at Windsor, the otherworldly Stonehenge and the beautiful spa town of Bath, but you’ll also get the opportunity to really get under the skin of the Cotswolds and learn about the authentic, rural culture that still exists amongst the rolling hills and quiet woodlands.

Battle your way through the ‘Parade of Seven Puddings’, sip a local ale at the regular haunt of J.R.R. Tolkein, and learn about the bizzare ‘Cotswold Olympics’.

With stunning views around every corner, excellent accommodation, wonderful pubs and beautiful cuisine, you are sure to enjoy an experience you won’t forget.


Cycle some of the most beautiful roads in the UK with a local guide who knows the very best routes

Try out some classic Cotswolds cuisine and the Parade of Seven Puddings

Relax in the very pub where the likes of J.R.R. Tolkein and C.S. Lewis used to visit

Your Local Host:


Will was born and raised in the Cotswolds. Following a family cycle trip in France, Will discovered a passion for active travel and brought it home with him. With the goal of showing off our beautiful English countryside in all its glory, through beautifully crafted active cycling, walking and adventure tours.

Experience Itinerary

A Royal Day Out

We collect you at 8.30 from London at Paddington Station, Platform 1, under the clock and take you by bus Windsor, which is about 1 hours’ drive.

As you get to know your group, our guides will fit you to your bikes and we’ll set off into the royal deer park, past the cricket pitches and the famous Guards Polo Club and grounds, founded by HRH The Duke of Edinburgh in 1955.

A former player, he remains the Club’s President today, regularly watching games from the Royal Box. His oldest son, HRH The Prince of Wales and grandsons, Princes William and Harry, have inherited his passion and have played many a game at the Club.

Often on a Sunday there is a polo match taking place right in front of us as we travel past, lingering longer when there is a Chukka in play!

After a beautiful loop of the Great Park grounds, with all of its eccentric statues, totem poles and ruins – including Leptis Magna aka the Temple of Augustus, an ancient Roman ruin from Libya that has ended up here, 2000 miles away from where it originated!

With the option to lunch in the famous Saville Gardens, Britain’s finest Oriental Gardens, or in Windsor Town itself, we take a private tour of the magnificent castle.

On a private tour, immerse yourself in the heritage of the largest occupied castle in the world, and 1000 years of royal history, led by an expert. For those wishing to stretch their legs, we can lead a tour through the cobbled streets of Eton and its historic colleges (select dates only) and museums. In the late afternoon, taking our bus to your hotel in Moreton-in-Marsh in the North Cotswolds means a nice, gentle start to your holiday.

Stunning Views and Seven Puddings

We wind our way through the majestic countryside of the Cotswolds, taking in some of the most well-known towns and villages including Broad Campden with its magnificent topiary, the golden-stoned Chipping Campden with its impressive market hall, built in 1627 and its fascinating civil war history – lived-out in the ruins on the outskirts of the town.

Cycling up and out of town we pass Dover’s Hill, home to the ‘Cotswolds Olympics’, founded by Robert Dover in 1612 and still going to this day! Popular competitive events include hay bale carrying and the Shin-Kicking World Championships!

We visit the imposing Broadway Tower, from where you can see 16 counties and to the Black Mountains of Wales, the perfect lunch spot with a view.

Today we also visit the stunning Hidcote Gardens for coffee and to explore its internationally renowned gardens – special because of its series of outdoor rooms and as the first National Trust property to be purchased for its gardens rather than the building itself.

For garden lovers there is the option to visit Kiftsgate gardens 200m around the corner, run by three generations of women and home to the famous Kiftsgate Rose.

We return by bike on our round trip to Moreton in Marsh in the late afternoon.

We organise an evening of entertainment to celebrate Great British Puddings; a light main course followed by a ‘Parade of Seven Traditional Puddings’, a true highlight of the week, with a vote for your favourite dessert over coffee – from Eton Mess to Sticky Toffee Pudding and Gooseberry Fool – which will you pick?


You can choose between a 3* country hotel or a 4* prestige hotel

bar in a country hotel

Opulent Palaces and Oxford Pubs

We cycle out from the hotel through the beautiful Cotswolds to Blenheim Palace, where Winston Churchill was born and a World Heritage Site. The morning’s ride is around 20 miles, through rolling countryside, stopping off at the famous organic farm shop, Daylesford.

Complete with cheese rooms, their own range of English wines, an incredible delicatessen, it is well worth a visit. Our coffee stop is the community run café de la post at Chadlington – boasting the ‘worlds best carrot cake – as voted for by Jeremy Clarkson, one of the regulars here!

At Blenheim itself, we provide guests with a sumptuous picnic spread over-looking the Capability Brown parklands and have ample time to explore the historical palace on an audio tour and walk through some of the 3000 acre estate.

There is the option to visit the tucked away and little-known graveyard of Churchill and his relatives, hidden just outside the Blenheim Estate. We travel into Oxford in the evening for a guided walk through the historical university town, from the Radcliff Camera to the Bridge of Sighs.

Timings-dependent, we can organise in advance to visit Christchurch Cathedral or an Oxford College. For those interested in literature we can visit the Eagle and Child for a local pint, famous for serving the Inklings literary group of C.S. Lewis, J.R.R. Tolkien and others as well as the pubs made famous by Inspector Morse!

With options for dinner in town including dining on the balcony of the iconic Ashmolean museum or in one of Oxford’s brilliant restaurants, we’ll truly explore the best of the city before returning to Burford and your hotel.


You can choose between a 3* country hotel or a 4* prestige hotel

country hotel in the cotswolds

Stepping Into The Past

We travel from Burford towards the stunning White Horse Hill, an ancient carving atop the Ridgeway, thought to be around 3000 years old. We wander to Waylands Smithy an atmospheric Neolithic chambered long barrow, haunted by the God-Giant Wade, King of the Finns.

Cycling to the White Horse pub in Woolstone for lunch, we continue by support vehicle onto Stonehenge, Europe’s best known prehistoric monument for a look around these magnificent stones, completing our Neolithic Day.

There is the option to finish at lunchtime and head straight to our hotel for a relaxing afternoon in Bath.

Why not try your hand at punting along the slow rivers and canals around Bath, take traditional afternoon tea in the celebrated Royal Crescent Hotel, or taking our famously funny Laugh at Bath tour through the city’s highlights, on this day or the next.


You can choose between a 3* country hotel or a 4* prestige hotel

hotel bedroom in the cotswolds

Downton Abbey and Roman Baths

In the morning we cycle around the canals of Bath towards Bradford on Avon and Lacock along tow paths and beside the rivers that lead into this Roman city. Visiting Lacock village takes you back 200 years, with very little changed in this medieval town.

This ageless quality has seen the village used for Downton Abbey filming, Harry Potter and in many other popular TV shows and films. Cycling back into Bath for the afternoon, we lunch in the Holbourne museum before taking a stroll for a privately guided tour of the incredible Roman Baths, constructed between 60-70 CE and one of the best-preserved Roman remains in the world.

Led by an expert on the Baths, you’ll gain a unique insight into its history. We take a relaxed walk through the cobbled streets in the early evening through the heart of the city, leading guests up to the Royal Circus and the iconic Royal Crescent with views overlooking the city.

We stay overnight once more in Bath, eating out in this town, known for its restaurants, bars, culture and arts!


You can choose between a 3* country hotel or a 4* prestige hotel

outside of a hotel in the cotswolds

Departure Day

Our tour ends in Bath after breakfast, where we help guests with their ongoing travel arrangements, most often from Bath train station, a short walk from the hotel.

Reviews (2)


Thursday 16th January, 2020

My 6-day cycling trip in Kent was wonderful. This was my 4th trip with this host (2 in the Cotswolds, 1 in the Cotswolds/Devon/Cornwall - a custom made trip - and then my trip in Kent in 2019). Each trip was outstanding: beautiful views, wonderful vi...

My 6-day cycling trip in Kent was wonderful. This was my 4th trip with this host (2 in the Cotswolds, 1 in the Cotswolds/Devon/Cornwall - a custom made trip - and then my trip in Kent in 2019). Each trip was outstanding: beautiful views, wonderful visits to national trust sites, historic homes, and monuments, and lovely hotels. The trips are well-organized and give guests the opportunity to add on or subtract miles as desired (in several trips I rode extra miles solo with the guide, which was really terrific). The organization is meticulous, and the guides are friendly, helpful, and very knowledgeable about the local area. Frances was a wonderful guide for the Devon/Cornwall trip!

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Linda B

Monday 9th September, 2019

Cornwall/Devon trips. I chose guided hiking but joined self guided guests and cyclists. The views were spectacular; the touring paths hidden gems; and the guides were outstanding. They were knowledgeable, intelligent, patient and told fascinating fac...

Cornwall/Devon trips. I chose guided hiking but joined self guided guests and cyclists. The views were spectacular; the touring paths hidden gems; and the guides were outstanding. They were knowledgeable, intelligent, patient and told fascinating facts about the region. Lodging and food top rated. And, I came back home healthier than when I left. I give my top recommendation to Will, Frances and the group. They have designed a unique small group experience. FIVE STARS!

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Location Information

You will be collected from Paddington Station in London at 8:30 am on the first day of your adventure, before you head out to Windsor, then to the Moreton-in-Marsh to begin your journey through the green rolling hills of the Cotswolds.

From there, you’ll head south through the Area Of Outstanding Natural Beauty, visiting Oxford, rural towns, and finishing the tour in the old Roman town of Bath.

  • 5 nights accommodation
  • All breakfasts and 3 dinners (in the brasserie/bar)
  • Entry into all iconic points of interest
  • Transport throughout
  • Professional local guide
  • Bikes and equipment


This tour is rated 2/5 for difficulty meaning it’s appropriate for guests going for a good ride and can handle an incline or two. The terrain we cover is varied. We’ll enjoy some rolling hills, with wonderful downhills and a few climbs which will be a bit more demanding.

Your holiday, however, will be tailored by your guide to suit your individual preferences. Rewarding views are guaranteed. Daily distances range from 10-40 miles and options for shorter or longer rides are available on all days.

You will spend two nights staying in The Manor or Redesdale in Moreton-in-Marsh, two nights in The Highway or The Lamb in Burford, and one night in The Bird in Bath.

All options are luxurious, comfortable and bursting with country character, and guarantee you a pleasant stay in the Cotswolds. There is free parking, wifi and upgrades available at every option.

Your luggage will be transported for you between accommodations by our team