Feefo service rating

Call us on 01707 817260

  • Monday - Friday9am - 5pm
  • Saturday9am - 1pm
  • SundayClosed
  • Bank HolidaysClosed

Call us on 01707 817260

  • Monday - Friday9am - 5pm
  • Saturday9am - 1pm
  • SundayClosed
  • Bank HolidaysClosed

Save up to £250 pp on your first booking with Ramble Worldwide. Learn more.

X Close

The South Cotswolds

Experience breath-taking vistas: Exploring the southern Cotswold escarpment near Cheltenham and Gloucester. The Cotswolds are renowned for picture-postcard beauty. Honey-coloured stone villages and open rolling grassy ridges.

  • Cotswolds

  • 5 nights
  • Half Board
  • Landscape

  • Sep

  • Average group size: 12-14


What does this mean?

What does this mean?

What does this mean?


View Destinations


Walking grade

Grade 4

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.  

Usual daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

The above statistics are generalisations of a day’s key walk, it does not include distance covered during general sightseeing or daily activity. Detailed information of the daily walking requirements are specified in the specific holidays ‘Daily Itinerary".


Classic Collection

Thoughtfully designed, meticulously planned, carefully graded, and expertly guided walking tours and hiking holidays along well-loved and off-the-beaten-track footpaths.


Holiday Highlights

  • Take in the view from Leckhampton Hill.
  • Walk the finest sections of the Cotswold Way.
  • Count the bizarre shaped yew trees in Painswick churchyard.
  • Enjoy the villages, many complete with manor house and church.
  • Discover Laurie Lee's hidden valleys.

As you journey westward from London, the landscape unfolds into an increasingly captivating tableau. The Cotswolds, renowned for their postcard-perfect beauty, unveil honey-hued stone villages and sweeping grassy ridges that stretch as far as the eye can see. Whether you're a walker, historian, geologist, or botanist, the Cotswolds offer an inexhaustible wellspring of fascination.

In this holiday adventure, we venture into the southern reaches of the Cotswold escarpment, nestled near Cheltenham and Gloucester. Here, we'll savour some of the most enchanting segments of the Cotswold Way. Our journey will lead us to Leckhampton Hill, where panoramic vistas of the Devil’s Chimney and the picturesque villages of Painswick and Winchcombe await. While the hills may not rise dramatically, they grant us just enough elevation to revel in breath-taking views stretching westward to the Severn Estuary and the distant Welsh landscape. As we pass through villages, keep an eye out for the splendid medieval churches, testimony to the prosperity generated by the local wool trade.

The riches of this region are compactly nestled, ensuring that travel from our hotel is brief, leaving ample time each day to immerse ourselves in the local treasures. This holiday promises a true postcard-perfect experience, an opportunity not to be missed for those seeking to bask in the timeless charm of the Cotswolds. 

*We also offer this holiday over the Christmas and New Year periods - please search for 'Festive South Cotswolds' for more details*.  

  • En suite four-star hotel accommodation on a half board basis
  • All local transport required for the itinerary by private coach
  • Services of a Classic Tour Leader
  • Entrance fees (unless otherwise specified)
  • Personal expenses (such as your bar bill)
  • Lunches
  • Discretionary tips
  • Optional excursions
  • Travel insurance

Holiday Information

Click the button below for a detailed Holiday Information Sheet containing all the particulars about this trip.

NOTE: Itineraries and Holiday Information Sheets can vary by a specific date chosen

View Holiday Information Sheet

Tour Codes


Itinerary & Travel

Itinerary Details

Whilst every effort will be made to adhere to the outlined itinerary and advertised programme, local conditions can change due to weather or other unforeseen circumstances. This may mean that routes and timings need to be amended or the order of days may change, sometimes at short notice.

Your Itinerary

Day 1

Arrival day




Independent arrival at the Cheltenham Chase Hotel. Check in is from 3pm. Dinner is at approximately 7.30pm in the hotel restaurant. 

Please aim to be in the hotel bar at 6.30pm - an hour before dinner - for an introduction to your tour leader, an outline of the planned programme for your holiday and the chance to meet your walking companions.

Day 2

Painswick Beacon, Coopers Hill & Roman Villa


Breakfast & Dinner


  • Time

    4.5 hours

  • Distance

    7.5 miles

  • Ascent/Descent


Our first walk starts in the attractive and elegant Cotswold town of Painswick, known as the Queen of The Cotswolds. We explore the historical streets and see the famous yew trees before walking through the Painswick Valley with a short climb up to Painswick Beacon. We will be rewarded with stunning views from the summit across the Vale of Severn. The walk continues along the Cotswold Way passing through woods to Cooper's Hill, then down to The Great Witcombe Roman Villa, before descending back to our hotel. 

Day 3

Kilkenny, Devil’s Chimney & Crickley Hill Country Park


Breakfast & Dinner


Views from the Devil's Chimney

The Devil's Chimney is a limestone rock formation that stands above a disused quarry in Leckhampton, near Cheltenham, Gloucestershire. It is named for its peculiar shape, that of a crooked and twisted chimney rising from the ground. The Devil's Chimney is a local landmark, but its origins are uncertain

  • Time

    4.5 hours

  • Distance

    8.5 miles

  • Ascent/Descent


A short drive in our private coach takes us to Birdlip from where we follow the Cotswold Way taking in Leckhampton Hill and the Devil's Chimney with spectacular views over the Severn Vale. We continue via the Cotswold Escarpment to Crickley Hill Country Park.

This is an undulating walk initially through farmland to an attractive village with Dick Whittington connections, before following the edge of the Cotswolds escapement along Leckhampton Hill to the unusual natural feature of the Devil's Chimney. There are great views on a clear day across the Vale of Severn towards the Malvern Hills and down onto the town of Cheltenham, before continuing on the Cotswold Way to wooded Crickley Hill.

Day 4

Winchcombe, Sudeley Castle & Hailes Abbey


Breakfast & Dinner


Hailes Abbey

Hailes Abbey is a majestic ruin in a peaceful setting situated on the Cotswold Way. The site is managed by English Heritage. 


  • Time

    4 hours

  • Distance

    8.6 miles

  • Ascent/Descent


Today's walk is based around the historic, medieval town of Winchcombe, once the capital of Mercia, home of King Offa. Winchcombe is rightly known as the walking capital of the Cotswolds.

We head off on the Pilgrims Way towards Hailes Abbey, a former Cistercian monastery, reduced to ruins by Henry VIII. From the Abbey we climb the Cotswold Way to the lovely hamlet of Farmcote with beautiful views across open farmland to the Malverns. In the afternoon we find the hidden treasure of St Keneln’s Well and discover its 1000-year-old legend. From here we descend with views of Cleeve hill and some of the best views in the Cotswolds to Sudeley Castle, home of Katherine Parr, sixth wife of Henry VIII.

After enjoying the castle parkland, we head back into Winchcombe to enjoy its uniquely Cotswold charm.

Day 5

Laurie Lee's Hidden Valley


Breakfast & Dinner


  • Time

    4.5 hours

  • Distance

    7 miles

  • Ascent/Descent


We start in Slad, Laurie Lee’s beloved home, bought to life in Cider with Rosie. We walk through Laurie's home valley, with stunning views and quiet glades. Leaving the Slad Valley behind we walk through undulating woods and valleys to Miserden with views down into the Golden Valley. Miserden is a chocolate box Cotswold village, where scenes of 'Cider with Rosie' were filmed due to telegraph poles having been removed by the Lord of the Manor.

Day 6

Departure day



Independent departure after breakfast. Check out of the hotel is by 11am. We hope you have enjoyed your holiday and we look forward to welcoming you on another soon.

Departure dates for your selected tour

28th Sep 2024 - 3rd Oct 2024 (5 Nights)

Travel Details

Private coach transport to and from the trailheads when necessary is included. 

Nearest mainland railway stations:
Cheltenham Spa station (5 miles)


Accommodation information

Below is the accommodation featured on this holiday across all departure dates. Please refer to the Itinerary for more detail about each night's accommodation for each departure date.

Delta by Marriott Cheltenham Chase

The  Delta Hotels by Marriott Cheltenham Chase is a comfortable, modern four-star hotel, with a superb health and fitness suite (including indoor pool) and is set in landscaped grounds on the edge of the Cotswold hills. Hardy’s restaurant and Hunter’s bar and lounge provide plenty of space to relax. The recently refurbishment and re-branded hotel provides a comfortable base to explore this magnificent corner of England. This modern and comfortable hotel is both well-appointed and set amongst the gently rolling hills and hidden valleys of one of Britain's most attractive walking areas.

Rooms offer en suite bathrooms, free Wi-Fi, TVs, a safe, air conditioning, a mini fridge and tea and coffee making facilities.

Trip Information

All the details you need

Holiday Grade

Usually, your walk will take up the whole day at a moderate pace. Terrain will often be hilly and paths generally good. Note that on holidays in mountainous areas, expect some rougher paths. An average walk length is 6 miles but expect this to vary from as little as 3 miles on a sightseeing day and up to 10 miles on a full day dependant on the amount of ascent and decent required.  

Usual daily walks - Distance: 6 miles; Ascent/Descent 500m; Terrain: sometimes hilly and undulating on good paths and tracks; Walking Time: Day walks. 

The above statistics are generalisations of a day’s key walk, it does not include distance covered during general sightseeing or daily activity. Detailed information of the daily walking requirements are specified in the specific holidays ‘Daily Itinerary".

Walks & Excursions

The Cotswolds, Britain’s largest Area of Outstanding Natural Beauty, cover 800 square miles of gently rolling and partly wooded hills dotted with attractive villages of honey-coloured local limestone.  The Cotswold escarpment, created when a block of the underlying rock fractured and tilted provides some spectacular walking trails including sections of the Cotswold Way which traverses 105 miles of Cotswold countryside from Chipping Campden in the north to Bath in the south.

Local Transport Costs

In the holiday cost, we've included all local transport expenses related to the advertised activity programme for your convenience. If there are additional visits or excursions to enrich your experience, you can choose to participate and cover the costs locally. Depending on the itinerary, local transport may involve a mix of private hire coaches, taxis, local buses, and ferries.

Optional Excursions

At your destination, you may have the option to book various local excursions and activities through a local operator. It's important to note that we are not involved in these activities or excursions, and we do not operate, supervise, or control them in any way. Your contract will be directly with the local activity supplier, and we bear no responsibility for their actions or omissions.

Spending Money

Holiday Budgeting

When budgeting for your holiday, you will need to consider drinks, non-included entrance fees, optional excursions you may choose to participate in locally and any souvenirs or additional services such as laundry. 


In your holiday price, we've included tipping for our local suppliers, covering hotel and restaurant staff, local guides, and drivers. Should you wish to make an extra contribution for a specific service, this should be given directly to the recipient at your discretion.

Tour Leaders & Local Guides

Tour Leaders

Your tour leader plays a crucial role in enhancing your holiday experience, and they share your passion for exploring the world on foot. In addition to being resourceful and organised they are also well-travelled and deeply enthusiastic about showing you new destinations.  Your tour leader takes care of all the local administration, ensuring you can fully enjoy your holiday without worrying about the logistics. While leading group holidays, they always keep in mind that each group is composed of individuals. Each tour leader brings their unique style, talents, and professional background to the table. Rest assured, they are all trained, qualified, experienced, and dedicated to making your holiday as enjoyable, interesting, and inspiring as possible. Remember, your leader, while on holiday, is your first port of call for any issues, ensuring a smooth and worry-free experience for you.

Leader's Evening Briefing

Each evening, your tour leader will meet with you to review the programme for the next day. This is your chance to discuss details and ensure that the planned activities align with your walking ability. If you have any concerns about clothing or equipment, feel free to bring them up during this discussion. If, for any reason, you prefer not to participate in the organised group programme, please inform your leader. Your preferences are important, and your leader is there to make sure your experience aligns with your expectations.

Your Travel Details

To reach the hotel…

by car: from the M5. Leave the motorway at J11A and join the A417 (signposted Cirencester). After 1.7 miles, bear left and at the roundabout take the third exit onto the A46 Shurdington Road (signposted A46 Cheltenham, Stroud). The hotel is shortly on your left.

by train or coach: The nearest train/coach stations are at Cheltenham and Gloucester. To get between your station and the hotel, use a bus or taxi as described. At Gloucester, bus-service 10 terminates at Clarence Street, which is close to the train station. At Cheltenham, services 10 and 46 go via Montpellier Street, which is about a mile from the train station.

by bus: Brockworth is served by the number 10 bus which goes to Cheltenham and Gloucester, and by the number 46 bus which goes to Cheltenham. Both services stop near the entrance of the hotel. For details of the timetables, please visit www.stagecoachbus.co.uk 

Taxis from Cheltenham to the hotel cost about £15 (Central Taxis 01242 228877) and from Gloucester to the hotel about £15 (Central Taxis 01452 382020). We do however recommend that you obtain a quote before you book.

You may also wish to look at the following website for advice on the best way to travel to the hotel;


Route planning to and from the hotel at Brockworth:

The AA and RAC both offer free and detailed on-line route planning facilities on their websites which may help you find our hotels. Details can be found at:



Personal Details Check

To ensure the accurate administration of your holiday arrangements, kindly verify that the personal details we have for you are current and correct. Confirm that you've given us all the necessary information for securing your travel and accommodation. Please review your passport details, date of birth, and any other pertinent information crucial for the management of your holiday.

Additionally, please make us aware of any dietary allergies or intolerances you may have. Your well-being is important to us, and this information will help us make appropriate arrangements for your meals during the trip.

You can access and update the provided information or add missing details through the "Manage My Booking" feature on our website at www.rambleworldwide.co.uk. Alternatively, reach out to our Sales and Reservations team at +44 (0)1707 331133. Upon receiving your booking confirmation, promptly check the details. Your cooperation ensures a seamless and enjoyable holiday experience.


This tour is offered on a half board basis, with breakfasts and evening meals taken in the hotel's restaurant. Lunches are not included in the holiday cost, however there will be opportunities to purchase lunches prior to your walks.

Footwear & Kit List


Lightweight waterproof walking boots with a good moulded sole (such as Vibram or similar) and a deep tread and which provide ankle support are strongly recommended and may be essential for some walks.

General Kit List

Outdoor activities are always safer and more enjoyable if you are prepared.

If you have not travelled with us before the following list might be of use:

  • Waterproof jacket (Goretex or similar) and trousers
  • Lightweight quick-drying trousers
  • Walking T-shirt/shirts
  • Walking socks
  • Fleece or jumper
  • Sun hat, sunglasses, lip salve and sun block
  • Warm hat and gloves (if appropriate)
  • Swimwear (if appropriate)
  • Day sack (this should be able to carry all you would need for the day's activity)
  • Day sack liner
  • Water bottle - at least 1 litre capacity (more than 1 bottle may be required)
  • Basic first aid kit
  • Lunchbox
  • Walking poles (should you find them useful)
  • Sit mat

This list is not exhaustive and every walker is different and may have their own preference.

Travel Documents Checklist

Documents and Information to take with you:

  • Holiday money
  • Credit or debit cards (and separate details of who to call if lost)
  • Car parking ticket and car park directions (if prebooked)
  • Coach or rail travel tickets (if prebooked)
  • Holiday booking confirmation document
  • Travel insurance details (if applicable)
  • Details of any medical condition or allergy your holiday leader should know about

Water To Go

Opting for filtered water from a reusable bottle with its built-in water filter, like the Water-to-go bottle available at www.watertogo.eu, is a sustainable alternative to single-use sealed water bottles. Simply refill it from any water source and contribute to saving the environment from disposable plastic bottles.

Exciting news: Water-to-go has introduced two new bottles to their collection. The Active bottle is designed to fit bike water bottle holders, and the Sugarcane bottle is an even more planet-friendly option. Crafted from fibrous cane, a by-product of liquid extraction, it undergoes a process to create plant-based plastic. Explore the details on the Water-to-Go website for this innovative new range.

As a token of appreciation for your commitment to the environment, we've secured an exclusive 15% discount with Water-to-Go for you. Visit www.watertogo.eu and use the code RWH17 during your order.                        

Note: If you're booked on a long-haul holiday departing after November 1, 2023, you'll receive a complimentary Water to Go bottle, sent to your home address 2 or 3 weeks before your holiday. Thank you for being a part of our sustainable journey!

Maps, Guidebooks & Other Information

Maps, Guidebooks & More

The walks are covered by the following map:

Ordnance Survey Explorer series 1:25,000
Map 179: Gloucester, Cheltenham & Stroud

The Map Shop

If you cannot find the maps or books locally we recommend:

The Map Shop
5 High Street
Upton upon Severn, Worcs

Tel: 01684 593 146
Website: www.themapshop.co.uk
E-mail: themapshop@btinternet.com

If you key many of the local places mentioned in this holiday fact sheet into YouTube, you will find a vast array of spectacular footage of the area.


Visit the following websites for an idea of the climate in your destination:

Staying Healthy On Holiday

Health requirements in destination can change, and it's crucial for you to take responsibility in staying informed. Ensure that you consult a professionally qualified source and comply with any health requirements at least 6 to 8 weeks before your departure. Your GP can provide advice on vaccinations. Stay proactive about your health preparations to ensure a safe and enjoyable travel experience.

Health Advice for United Kingdom

No compulsory immunisations are required for holidays in the UK although you should be up to date with the usual immunisations recommended for life in Britain. Tetanus immunisation is recommended.

Further Travel Advice

For further advice please visit:

You might wish to take a small bottle of antibacterial hand gel with you for times when you're unable to wash your hands.

Travel Insurance

It’s a condition of booking that you obtain adequate travel insurance, from a reputable provider, to undertake the holiday, including UK trips chiefly due to the cancellation element of cover.

The policy must cover the period from the date of booking to the last day of your trip and should include, as a minimum, cover for: medical expenses (including the consequences of a Covid positive test result), mountain rescue including helicopter rescue, death, repatriation, cancellation and curtailment and shall not have exclusion clauses limiting cover for the activities you will partake in on your trip, including altitudes reached in the holiday arrangement. It is your responsibility to check that your policy is adequate for the nature and destination of the holiday booked.

Once you have obtained your travel insurance, please provide us with the name of your travel insurer, the policy number and the insurer’s 24 hour emergency assistance number.

In the event that you fail to obtain suitable Travel Insurance we shall not be liable for any costs incurred or claims made against us due to your failure to comply with this term.

If travelling outside the UK you must carry proof of insurance with you and produce it if reasonably requested to do so by RWH Travel staff, tour leaders or suppliers. No refunds will be made should you be excluded from the walking programme through being uninsured or you being unable to demonstrate that you are insured.

Our house broker MPI should be considered for whom we are an affiliate and contact information is on our website and will be referred to in your booking confirmation.

If you are travelling to an EU country or Switzerland please also ensure that you have either an existing valid EU EHIC card (European Health Insurance Card) or a valid UK GHIC (Global Health Insurance Card). You can apply for a UK GHIC free of charge on the NHS website at https://services.nhsbsa.nhs.uk/cra/start.

Personal Safety

The UK Foreign, Commonwealth & Development Office is your go-to for the latest info on security, local laws, and the nitty-gritty of passports and visas at www.gov.uk/travelaware. Make sure to take a quick peek at the current advice for your upcoming destination—it'll only take a few minutes.

When you're out and about, stay aware of your surroundings. Take smart precautions with your credit cards and passport, and maybe tone down the flashy accessories. Less is more, especially when it comes to carrying cash—just enough for the day will do. Consider using a money belt for that extra layer of security. Stay alert, stay safe, and make the most of your travels!

Cultural Awareness

Responsible Travel

We are dedicated to promoting responsible travel practices that prioritise the well-being of both the environment and local communities. We believe in the transformative power of travel and aim to minimize our ecological footprint by selecting eco-friendly accommodations, encouraging waste reduction, and supporting sustainable transportation options where possible. Our walking tours are designed to immerse participants in the local culture, fostering meaningful connections with the communities we visit. We strive to leave a positive impact by engaging in responsible tourism activities, respecting local customs, and contributing to the preservation of natural landscapes. Through our commitment to responsible travel, we aim to create enriching experiences for our guests while actively contributing to the conservation of the destinations we explore.

The Ramble Worldwide Outdoor Trust

Unlike many other tour operators, we take pride in our unique approach. Ramble Worldwide channels its surplus profits back into various outdoor, walking-related, or environmental conservation projects in the UK through our own trust. When you choose us, you contribute to this impactful initiative.

The Ramble Worldwide Outdoor Trust is passionate about making the outdoors more accessible for more people from all communities. We grant funds to many organisations and have recently partnered with Mind Over Mountains, Adaptive Grand Slam and other groups to create an enduring impact on people’s lives and to support them to enjoy the outdoors. In addition, the Trust makes many small grants to local organisations such as Ramblers Groups, Walkers are Welcome, My kind of Books and recently provided a small grant, via his scouting group, to enable a young man whose family had fallen on hard times to complete his DofE Gold award.

Patron of the Trust is the renowned explorer, Mark Wood. Over 20 years Mark has undertaken expeditions to some of the most remote parts of our planet. Our shared values make for an exciting partnership, and we believe that by standing shoulder to shoulder we can encourage people from all communities to enjoy being active outdoors in whatever way suits them best.

For more comprehensive details, please visit the 'About' section on our website and click on the Charitable Trust link. Your choice to travel with us goes beyond a memorable vacation; it contributes to meaningful projects that have a positive impact on our community and environment.

Heart and Sole

We appreciate that we are in a fortunate position to be able to use our profits to help make a difference to people's lives. Heart & Sole is a venture managed by our office staff, whose aim is to reach the heart of the communities in the countries we visit. Through Heart & Sole, we hope to make more of a long term, direct impact to these communities, particularly in less developed countries where even a small amount goes a long way. See our website for more information and details of some of the projects we support.

Staying In Touch

Mobile Phones

Kindly share a mobile phone contact number with us. We'll utilize this solely for crucial communication pertaining to your holiday arrangements.

Ensure your mobile phone remains switched on and easily accessible when en route to the airport or during transit delays. This way, we can promptly reach you with any last-minute updates concerning your travel plans.

In consideration of others, we request that you switch off your mobile phone during walks or make an effort to limit its usage. Additionally, during group meals, please minimize the use of mobile devices. Your cooperation ensures a seamless and enjoyable experience for everyone on the journey.


What customers are saying

View Dates & Book

Choose your preferred departure date

Can't find what you're looking for?

Call for help or regional flights on 01707 817260

View Dates And Book
Feefo service rating