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What to expect

Areas of Outstanding Beauty

Areas of Outstanding Beauty

Discover quintessential English towns

Four-Star Hotel

Four-Star Hotel

Leonardo Hotel Cheltenham

Winchcombe

Winchcombe

Visit the ancient Saxon capital

Relaxed Walking

Relaxed Walking

Follow the Cotswold Way

About this trip...

Discover some of the UK’s most picturesque landscapes and finest walking trails in the world-renowned Cotswolds – celebrated for its charm and natural beauty. Stay in a superb four-star hotel and enjoy expertly guided walks in the company of like-minded travellers on this ever-popular Solos walking break.
 
Grade: Easy to Moderate
Activity Level: Activity Level Rating
What's this?

What's included?

  • Twin/double room for sole use with private facilities
  • Breakfast & 3 course evening meal daily with glass of wine
  • Welcome drink & information meeting
  • 2 Full Day guided walks, including transfers
  • Experienced Cotswold Blue Badge walking guide
  • Accompanying Solos Tour Leader

What's Extra

  • International flights are not included
  • Let us help you book them! Learn more.
  • Travel insurance
  • Tips & drinks
  • Meals when not included in the itinerary
  • Activities when not included in the itinerary

Itinerary

  • Arrival Day
  • Cotswold Way & Ancient Mercia
  • Cotswolds Woodlands & Grasslands
  • Departure Day

What you'll be doing

Day One: Arrival Day

Day One: Arrival Day

Check in at leisure and perhaps enjoy the hotels facilities then meet your fellow Solos guests for the first evening dinner.
  • Dinner included
Day Two: Cotswold Way & Ancient Mercia

Day Two: Cotswold Way & Ancient Mercia

Our first walk begins in the historic town of Winchcombe, often considered the capital of ancient Mercia—one of the original seven Saxon kingdoms. From here, the trail leads us through a peaceful pastoral valley before opening up to sweeping stretches of farmland, where you’ll likely see the region’s iconic sheep grazing in the fields. Along the way, we’ll visit several notable landmarks:

  • St Faith’s Church – a historic site with roots stretching back to Saxon times.

  • Farmcote Herb Garden – a delightful stop to take in the colours and scents of a wide variety of herbs.

  • Hailes Abbey – a Cistercian monastery founded in 1246, rich in medieval history.

  • Hailes Church – known for its striking medieval wall paintings and stained glass windows.

We’ll pause for refreshments at Hayles Fruit Farm, the perfect place to sample local treats. The walk concludes back in Winchcombe, where there’ll be time to unwind and enjoy a well-earned drink at one of the town’s cosy pubs or cafés.
  • Transfer time: 30 mins approx 
  • Walking distance: 7.5 miles approx (Steep in parts with stiles) 
 
  • Breakfast & dinner included
Day Three: Cotswolds Woodlands & Grasslands

Day Three: Cotswolds Woodlands & Grasslands

Today’s walk takes us on a charming route through scenic woodlands and open grasslands, carefully maintained to support diverse wildlife—including several orchid species and the rare Duke of Burgundy butterfly. As we follow the trail, we’ll be rewarded with sweeping views: the rolling Painswick Valley on one side and the striking Malvern Hills on the other. On a clear day, you may even catch sight of the Severn Estuary, the Forest of Dean, and the distant Welsh hills.

We'll pause for a well-deserved break at the welcoming Edgemoor Inn, the perfect spot to relax and enjoy some refreshments before we continue our walk.

Transfer time: approx. 20 minutes
Walking distance: approx. 6 miles

 

  • Breakfast & dinner included

Day Four: Departure Day

Day Four: Departure Day

After a leisurely breakfast, check-out and say goodbye.

  • Breakfast included

Accommodations

Leonardo Hotel Cheltenham

Nestled just outside the vibrant town centre, the four-star Leonardo Hotel Cheltenham offers an ideal base for discovering the surrounding area, while its excellent facilities make it a perfect spot to unwind in the Cotswolds.
Facilities include:
The Leonardo Hotel Cheltenham offers state-of-the-art facilities including a fully-equipped gym, indoor heated swimming pool, steam room, sauna and spa pool. There is a bar and restaurant offering all day dining and a bar to relax with your favourite tipple. WiFi is available throughout the property and there is plenty of parking available for a fee.
Room includes:
Rooms are stylish and modern with contemporary artworks, equipped with WiFi, TV and tea and coffee making facilities. The bathroom has a bath or shower, complimentary toiletries and hairdryer.

Dates & Prices

Departure Return Nights Price from Other Info
Apr 16 2027 Apr 19 2027 3
$969
  

Essential Information

Travel Insurance

We strongly recommend purchasing travel insurance before any trip — it safeguards you against unexpected issues like illness, cancellations, or lost luggage. It also protects your health and travel investment, giving you peace of mind to fully enjoy your journey. Click here to learn more.

Passport & Visas

We recommend that you check passport and visa requirements for the country you are visiting at the State Department if you have a U.S. Passport. Most countries require that your passport have at least six months validity when traveling internationally, and many require that you have one to two blank visa pages for either an entry stamp or visa. As a general rule, please check that your passport has six months validity beyond your planned trip, and if not, please renew your passport with plenty of time to provide Solos with your updated passport information by the final payment due date.

Not sure what travel documents you need? Our trusted partner, sherpa°, makes it easy to check visa and entry requirements based on your destination and passport. One quick check now means smooth sailing later. Click here to learn more.

Location & Transport
The hotel is conveniently located a short distance away from the A40 and Cheltenham Spa Station is 1.4 miles away. Car parking is available at a reduced rate of £7 per day. The postcode for Sat Nav is GL51 0TS.
Walking Programme
Two guided walks are included in the programme. The walking programme requires good physical fitness and you can expect to walk approx 7.5 miles on the first walk and approx 6 miles on the second walk. A coach will be used to transfer you to the start/end point of the walks. 

It is recommended to purchase a snack and drink to take with you before each walk. Lunch on both days will be at own cost. It is your responsibility to ensure that you are fit and well enough to take part in your chosen activity holiday. 
 
If you are unsure as to whether the walks are within your capabilities, please contact the office to discuss this matter, thus making sure you appreciate the terrain that you will be walking. You could be walking across uneven ground in some areas and extreme care must be taken, especially if wet. If used to using a pole/stick, it is advisable to bring it.
 
Please appreciate the route and content of the holiday may change at the time and at the discretion of the guide/organiser, should conditions require. Solo’s Holidays Ltd cannot be held responsible for personal injury, accident or damage to property whilst on these walks other than incidents arising out of the company’s negligence. The guide has the right to refuse to guide a walk with anyone not properly attired.
What to wear
It is of paramount importance that you have the correct footwear. It is essential to wear walking boots that are comfortable and preferably lightweight, with some ankle support and a good grip. If you already have a pair of boots that you are happy walking in (including during hot/wet weather and on hard ground), then bring these along. However, if you are bringing new footwear, do make sure they are well broken in before you arrive. Experience has shown that wearing 2 pairs of woollen socks adds to comfort. The weather, even in summer, can be unpredictable. We would therefore recommend you travel with clothing suitable for all conditions, and suggest you use the following checklist as a guideline of what to take:
  • Walking boots with good ankle support
  • Waterproofs – jacket and trousers
  • Walking poles – recommended as they provide good support for the knees, particularly on downhill sections of walks and when conditions are wet/slippery
  • Lightweight trousers and shorts with pockets
  • Shirts or t-shirts for walking in
  • Walking socks – several pairs
  • Lightweight fleece or jumper
  • Hat & gloves
  • Daysack/rucksack for walking
  • Umbrella – it can be used also for protection from the sun as well as rain
  • Lightweight drinking bottle to carry water whilst walking
  • Small first aid kit – plasters, insect repellant, etc
  • Good, high factor sunscreen, sunhat and sunglasses.
Gratuities
There is often confusion on the question of gratuities, since it frequently depends on the type of holiday, location and, of course, your attitude towards tipping, as to what is normally expected. In order to give you a rough idea, we have given appropriate guidance below. The Tour Leader will be on hand to offer advice or suggestions if required but gratuities are offered entirely at the sole discretion of the individual. We suggest a group collection at the beginning of your holiday to cover drivers, guides, porters and hotel staff (including restaurant, kitchen and reception staff) of approximately £10. Your Tour Leader will collect this on your behalf and distribute it accordingly, thus relieving you of the burden of who, when and how much to tip. The tipping of bar staff and housekeeping will be left to your individual discretion (the rounding up of the drinks bill and a small amount left in your room on departure should cover this and would be much appreciated). For any meals that are not included in your itinerary, restaurants expect a 10% gratuity (do check that service has not already been added to your bill). For taxis 10% of the metered fare.
Health Requirements

We recommend that you check if vaccinations are required for your destination at the CDC’s recommendations for your visited destination(s). We also recommend you purchase travel protection. A travel protection plan can often assist with medical emergencies and reimburse costs that are covered by the plan. Please verify coverage details with Solos before you travel.

Flights & Airport Transfers

Whether you'd like us to arrange your flights or prefer to book your own, we're here to make the process easy. Our team can secure flights from the location that suits you best or provide all the arrival and departure details you'll need if booking independently.

Arrival & departure airport transfers are included for the majority of our trips EXCEPT our UK Breaks, regardless if you book your own flights or if we book them for you. To learn more about flight options, payments, and transfers, click here.

Rated as Excellent (4.8/5) by our customers

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Fantastic time

I’ve recently returned from my first Solos trip and had a fantastic time. I can honestly say that I enjoyed every minute, and the memories will last a lifetime.
-Patricia

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Highly Recommended

I’d highly recommend Solos to people looking to travel on their own with a group of like minded people.
-David

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Brilliant Week!

We laughed until our bellies ached. It was such a brilliant week.
-Janev

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Go for it!

I still get a bit nervous but this will be my third time with Solos and its one of the best decisions I have ever made- everyone is so friendly, just go for it!!
-Jane

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