Exploring the Cotswolds - 8 days

Exploring the Cotswolds - 8 days

Trip Highlights

  • Discovering the typically English countryside
  • Walking parts of the Cotswold Way
  • Enjoying the flexibility of walking with a daypack from village to village
  • Experiencing the hospitality in the warm family run B&B’s and guesthouses

Trip Summary

This holiday is intended to appeal to those who want a gentle introduction to walking in the English countryside; the Cotswold’s are hilly rather than mountainous - the highest point being little more than 1000 feet above sea level. Officially designated as an Area of Outstanding Natural Beauty, the Cotswold landscape is an entrancing mixture of parkland, cultivated fields with dry-stone walls of Jurassic limestone, and patches of unspoilt woodland. Stone-built, also, are almost all the cottages, farmhouses, villages, and small towns that our route passes. About half of our itinerary, around 50 miles (from Stratford-upon-Avon to Winchcombe), coincides with the Cotswold Way, a 102 mile Long Distance Path that is claimed to be the best waymarked in England.


We grade this walk as ‘Easy - Moderate’ in relation to our other U.K tours, the route is hilly, but not mountainous, the weather is rarely too bad for walking, and there are generally quite a number of villages enroute. Days of up to 20 km are not too long for most reasonably fit people.


Make your own way to Stratford-upon-Avon, the birthplace of William Shakespeare. The day is free to explore the town. You can visit Shakespeare's birthplace in the centre of town, the Holy Trinity Church where he is buried, and the thatched cottage where Anne Hathaway once lived. Accommodation: Moonraker House is a traditional English 4 star licensed bed & breakfast with en-suite rooms, delicious home cooking, friendly service and a cosy atmosphere.

Meals:  Nil

Today's walk will bring you to Mickleton. We suggest that you stop off at the National Trust Gardens at Hidcote Manor, near Mickleton. Enjoy the wide views over the vales of Severn and Avon toward the Malvern Hills and Wales. Accommodation: The Three Ways Hotel is home to the famous Pudding Club and its award winning restaurant.

Meals:  B

Today you will walk to Broadway via Chipping Campden Fish Hill and the unique Broadway Tower, which offer remarkable views of the Cotswolds. Broadway is a beautiful and picturesque town, and the main street is lined with magnificent stone-built houses as well as some great antique shops. Accommodation: You will receive a warm welcome at the 4 star Windrush Guesthouse.

Meals:  B

On today's walk to Blockley you will pass Buckland where you can take a little time to explore, the church is interesting and has medieval painted roof timbers. Laverton, Stanton and Snowshill. A visit to the Tudor Snowshill Manor, with its collection of art and artefacts from all over the world, may be of interest. Blockley bears some resemblance to the villages of the Stroud Valley but the stone is much more golden in colour. During the 18th century when the wool industry was in decline Blockley turned to silk production. The village is a unique collection of buildings reflecting its past glory of mills and silk production and is quite different in, character to other north Cotswolds villages. Accommodation: The Crown Inn Hotel is an enchanting historic building. You have to pay for your breakfast directly to the hotel.

Meals:  Nil

Today is a beautiful walk, and you will be able to explore some of the prettiest villages of the Cotswolds. To the medieval wool town of Bourton on the Water, the walk will take you via Batsford, Stow on the Wold and Lower Slaughter. The river Windrush flows down the main street of Bourton on the Water. Bourton is well known for its footbridges over the river Evenlode and for its scale model of the village. Accommodation: The Lansdowne is a family run 4 star guesthouse where you can expect a warm welcome on arrival.

Meals:  B

An easy schedule today, which allows ample time to explore Bourton on the Water with its many attractions before setting out on your walk. Guiting Power, nestled in the hills above a small valley, is a perfect example of a Cotswold village. Due to limited accommodation in Guiting you may be staying in the small village of Naunton which is located 1/2 hour walk before Guiting. You will through this village enroute. Accommodation: Due to the limited accommodation in Guiting Power you could be staying at a) Guiting Guesthouse, Guiting Power, the house was originally built in the 16th century and could tell a story or 2 if the walls could talk. b) in the small village of Naunton which is located approx 2 miles before Guiting Power.

Meals:  B

The walk today leads you to the atmospheric ruins of Hailes Abbey, destroyed under Henry VIII, and the still inhabited Sudeley Castle, where Henry VIII's last wife Katherine Parr lived. Winchcombe is a delightful town nestling in a deep valley near the regency town of Cheltenham. Accommodation: Wesley House is a 15th century merchants house, and its restaurant developed a reputation for excellent food, elegant surroundings and exemplary service. If you arrive here on a Saturday night then we have to book you as dinner, bed & breakfast and there is a supplement of approx £50 per person.

Meals:  B

Your trip concludes after breakfast.

Meals:  B

What's Included

  • 6 breakfasts
  • 7 nights B&B accommodation on a twin share basis usually with ensuite facilities
  • One piece of luggage per person transferred from Inn to Inn, not exceeding 20kg
  • Information pack including route notes & maps (1 pack per room booked)
  • Emergency hotline

What's Not Included

  • Travel to Stratford and from Winchcombe
  • Lunches, dinners and drinks
  • Transfers
  • Items of a personal nature
  • Travel insurance

Upcoming Travel Dates


Trina Willis did a good job answering questions, and helped us with handling of extra bag. The accomodations in general were good, with Three Ways House our favorite, as it had both a very nice room and great restaurant. Diane enjoyed the Pudding Club. The two not up to the same standards on rooms were the The Crown Inn in Blockley and the Wesley House. However, the restaurants were good with the Wesley House very good. In general we enjoyed the hikes. In the future we would be more interested in hikes where we had a base camp and could stay for 3 days, rather than moving each day, which required constantly repacking of our luggage.

N Nowicki, Illinois, USA, 07 Oct 2019

We enjoyed a lovely week of walking in this beautiful part of England. We can't speak highly enough of the accommodation. The notes and maps provided were excellent.

P Snape-Jenkinson, QLD, Australia, 11 Jun 2019

We had the most fabulous time in every way possible. The weather was so sunny and warm that we never used our rain jackets that we brought along with us. The walking footpaths were perfect as were the maps that you sent for us to follow. Our accommodations were all wonderful - - our favorites were Mil-Mar in Stratford (sweetest couple running the B&B there), Three Ways Hotel in Mickleton, and Lansdowne in Burton-on-the-Water. The Sherpa service was absolutely perfect and we recommend them without reservation. What an absolutely delightful holiday. Thank you so very much for attending to all the details.

B Hamlin, Washington, USA, 30 Oct 2018

Too many high points to name - ancient old villages (day 5 had the most), beautiful views of countryside, sheep with newborn lambs everywhere, beautiful fields with hedges all around, all the fruit trees in color, woods with huge old trees, friendly people, pubs. There was a lot of mud due to heavy rainfall before we arrived, it made the steep descent on day 2 very difficult. Strongly recommend 100% waterproof boots, rain pants, walking sticks and know how to read a compass before travelling.

S. Wade, Toronto, Canada, 14 May 2018

Sherpa were very thorough in providing detailed route notes and interesting information about the places we walked through, as well as topographic maps (good photocopies, numbered in sequence) and local town maps / brochures. Only in a few cases was it evident that some of the information might have been a bit out-of-date, always a bit disconcerting when you need to turn left instead of right etc, but you get by.

L. Haegi, Unley, SA. Australia, 08 Jun 2015

Fabulous countryside. Beautiful experience walking through a variety of environments and gorgeous villages.

C. Braunack, Graceville, QLD. Australia, 13 Jul 2015

The scenery was amazing - loved the lot! Cotswolds - 3 Ways House accommodation and food superb. Particularly liked Blockley Village, Lower Slaughter and Sudley Castle. All accommodation great and enjoyed every day of walking. Thankyou!

M. Findlay, Macmasters Beach, NSW, Australia, 21 Sep 2015


Duration:8 Days
Starting Point:Stratford-upon-Avon
Finishing Point:Winchcombe
Activities:Self-Guided Walking
Grade:introductory to moderate  Click for more information
Trip Code:UCO
Prices From:GBP£840 Per Person
2021 Single Supplement:GBP£320  Click for more information
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.